The Tech Guy

Date and location of meeting: San Francisco, March/April 2017

Okay, so I am writing this from NYC (where I now live!) and am basically in love with this guy I met in San Francisco last week.

I arrived in San Francisco at the end of March, and as usual, got to swiping as soon as I landed. It was a Friday, and I had spent the day walking the Golden Gate Bridge, was forced to catch two buses to get home due to my phone running out of battery, and was consequently exhausted. I wanted to rest for the evening but I also would not have minded winding down with some wine.

Enter Tech Guy.

We had been messaging since I arrived in SF. Tech Guy had super liked me, and I swiped right out of obligation. I thought he was boy next door cute, but by no means was he a mega babe.

So that Friday night, I came home exhausted from walking the bridge and was preparing for a night in when Tech Guy messaged me saying he was probably going to have a “calm night” and to let him know if I wanted to meet up for a drink. In the early evening, I replied that I’d like a drink, and we then made plans to meet up for a drink later that night at a dive bar within walking distance of both of us.

Around 7:45pm that night, I got ready and left my place. I was dressed casually in a black denim mini, striped turtleneck, denim jacket and black ankle boots. He got to the bar a little earlier than me and walked up the street to meet me. My suspicions were confirmed when I saw him – he was only a little bit taller than I was. He was not hideous but not the usual 10 that would warrant a hook up on the first night.

Nevertheless, we went to elbo room. I was unsatisfied with his bar choice – it was a large dive bar with ageing decor, that smelled like alcohol had seeped into the furniture. The staff were tattooed, and they didn’t serve wine. Masking my discontent, I ordered a gin and tonic, and sipped it slowly while Tech Guy asked numerous questions about me and I answered them politely, asking him questions in return.

Tech Guy was 31 (but looked younger), white, and worked for a well known social media company. He was originally from New York, but moved to SF in the last year. He asked me a lot of unusually direct questions, such as the name of my ex, which I found a little odd, but thought he might be nervous or shy. We finished our drinks and then walked outside. I was almost ready to call it a night, but then he asked if I wanted to grab another drink elsewhere. I told him that I usually drink wine, and he said he knew a place nearby.

We walked about 10 minutes to a nearby wine bar. At this point, I was already a bit drunk – those American bartenders and their free pours! The wine glasses at the bar we were at also abnormally large. As I hadn’t had a large dinner, I could feel myself getting very drunk very quickly, and at this point, was freely offering up information about myself to Tech Guy that I wouldn’t normally have. I got fairly drunk at the wine bar, and don’t remember many things I said, or how long we stayed there, but after we finished our glasses, Tech Guy settled up the bill and as we walked outside, he asked if I wanted to come to his place to watch a movie, no expectations. Of course, drunk me acquiesced, but with no intention at all of hooking up.

We walked back to his place and I must have been babbling drunkenly at this point, but also remember feeling overwhelmingly tired. I was relieved to get back to his place. He lived in a cute studio apartment in Hayes Valley. After we got back to his place, he put Moonlight on, which undoubtedly, was kind of heavy for a Friday night and first Tinder date.

After he put the movie on, he told me to lie down, and I rested my head on his lap. He would lower his head intermittently and kiss me on the forehead, which soon progressed to kissing, with tongue, but only after he asked if he could kiss me. And from kisses on the lips, it progressed to heavy petting. We then moved to the bed, where he peeled my clothes off hungrily, and then said he was going to go down on me. His technique was not terrible, but not the best I have had. Afterwards, he asked if he could fuck me- I said yes.

The sex was quite pleasant despite that I was half asleep/drunk and couldn’t do much. He had a large penis, which surprised me because of his height, and lankiness. We had sex once, for 10 minutes or less, before he came. After that, I think we lay in bed talking or kissing, in which he gave me many compliments, saying I was really beautiful, and that I had a perfect vagina. We had sex again, the second time was a bit more rough, which I preferred. After that, we fell asleep, but I woke up in the middle of the night, and Tech Guy was also awake. We started talking again, and kissing, and eventually had sex again. Like the other times, it was short. He was extremely affectionate with me, and held me all night, and asked if he could buy me breakfast in the morning. I said yes, and asked him if he always tried to take all the girls he met from Tinder home on the first night. He said no, but that I was so cute and only here for a few nights, that he had to try. With my head sufficiently larger due to all the compliments in the space of one evening, I fell asleep, content, wrapped in someone’s arms.

The next morning, I woke up due to the light streaming in through the window, and promptly stated my discontent. I told Tech Guy, I didn’t understand how anyone could sleep without blinds, and asked if he had an eye shade to cover my eyes. He went to get me one, and I tried to go back to sleep, but had a throbbing headache. We continued talking, and he continued giving me compliments, my favourite of which was: “Everyone’s going to love you in New York”, spoken with genuine warmth and enthusiasm. We then joked about how seedy it looked, with me on the bed, wearing the blindfold, and my arms stretched above my head (little did he know what I was into). All morning, he had also been joking about adding me on Facebook and liking all of my posts.

Shortly after this, he led my hand to his penis, once again, erect, and while I stroked it for a few minutes, I was not in the state of mind for morning sex. After asking if I was up for morning sex, and receiving a no, TG asked I would do him a “huge favour”. I asked what it was, and Tech Guy replied, “Will you watch me masturbate?”

I said sure, and engaged in a bit of voyeurism for the next few minutes. He came on my stomach, and afterwards, I took a shower and got ready to head out for breakfast. When I came out of the bathroom, he was sitting on the bed, wearing glasses, and I thought he looked adorable like that, and wondered why I hadn’t realised it earlier. We chatted for a little while, before he hopped in the shower, and shortly after, we walked to a nearby cafe for breakfast.

After being seated, we started talking politics, and as usual, whenever I get on the topic of politics, went into an anti-Trump diatribe. He shared my sentiments, and then said he loved hearing my opinions. After brunch, he walked me to the BART stop. We chatted all the way there, and he would kiss my forehead intermittently as we walked. When we got to the BART station, he gave me his clipper card to use, but said the card would warrant a second meeting on either Sunday or Monday. He suggested I come to his office on Monday for breakfast, and he would show me around.

Later that day, he messaged me saying he was glad we got the chance to meet up. We continued messaging back and forth until Monday, when I came to visit him at work and I scored a free breakfast (yay for tech companies and free food!)

We sat there bantering over breakfast, and as we did so, TG said he had a speech to give me when he showed me around later. After eating breakfast, he basically showed me around his entire office, and introduced me to his colleagues. The office spanned three or four levels, had games rooms and an outdoor deck- I was burning with jealousy the entire time. At the end, he took me into a room designated for what seemed like hanging out, and we sat in a square sofa booth. We were the only people in the room, and he said he was going to give me the speech now.

He began with, “I just wanted to say I really like you, and I think you’re so cool and it wasn’t just a random hookup.” There was definitely a bit more but my memory is quite hazy. At the end of the speech, he told me to come in for a kiss. It was all very romantic comedy-esque. After the kiss, I told him I didn’t have a speech for him, and thought he was joking when he said he was going to give me a speech earlier. Right after that, I decided it was time to leave for my flight to NYC. TG said he’d walk me to the BART.

While walking there, he told me he would be in NYC in June and would love to see me then. With that, we parted, and I left SF full of warm, fuzzy feelings.

The Irish Boy

Date and location of meeting: New Orleans, October 2016

R+ material***

While I was in New Orleans, I matched with a beautiful boy. I spent the day out sightseeing in New Orleans, and had come back to my hotel after a couple of drinks on Bourbon Street and Frenchmen Street, and was preparing for bed, when I got a message from him, saying “Damn – you’re hot AF”.

It was not the kind of response that would usually elicit a response from me, but damn, Irish Boy was hot AF himself. We exchanged a few remarks, after the ‘hot AF’ opening line, and figured out our hotels were within a 20 minute walking distance of each other. Irish Boy said he could come up for a drink. And that was how I ended up with an Irish boy in my bed, at 3am.

He got up to my hotel room fairly quickly and knocked at the door. It was only at this point that I accepted the full scope of what I had done, ordering a boy up to my room, like pizza. I peered through the peephole, and saw a tall, beautiful stranger standing there, and opened up. He looked like a young Tom Cruise, with slightly tan skin, blue eyes, shaggy brown hair, and a smile that could melt butter.

He said my name when I opened the door, and asked if he could come in, and then if he could sit on the bed. I wasn’t expecting a boy who used expressions, like ‘hot af’, to be so polite. It was also when I first met him in person that I realised he was Irish, and him, that I was Australian. He remarked, “oh, your’re Australian,” as he strolled into the room, and we began an easy conversation about ourselves, our backgrounds, and what we were doing in New Orleans. Just as you would on a regular date, only we were sprawled in bed. Irish Boy was 28, from Dublin originally, but moved to NYC with an NGO he had been working for for some time. Prior to that, he’d worked in the economics department for another intergovernmental body. He was visiting New Orleans for the week, with his brother.

Not my usual type. Contrary to what I’d thought, he was soft-spoken and gentle. After 15-20 minutes of talking, he asked if he could kiss me, and I assented. He tilted my head towards him, and as he leaned into me, he said, “you’re beautiful,” before he parted his soft lips and kissed me. It was one of those kisses where you feel everything just falling away. Not long after, we were taking our clothes off, and he graced me with his beautiful body. Irish Boy is the first boy/man I have ever seen, to have an actual 6 pack. After we were both undressed, we did some naked kissing, before he decided to put it in. He came prepared, with a condom, which he put over his giant penis. And then, wildness ensued.

He was a bit rough, liked to talk dirty, spanked me a lot, put his finger inside me, and then in my mouth, and watched in a fascinated sort of way. All things I liked. We were done in an hour, or just short of an hour, and I thought he’d be on his way, but then he stayed for a little while, and I rolled onto his chest and he held me, and we discussed Trump, and Brexit, and things people don’t normally talk about after having rough, dirty sex. Before long, he slipped into the conversation that he had to be up early, and I took the cue to move away and watch him put on his clothes, and say the usual, it’s been fun, before heading out.

And when he was gone, I revelled in the space of an empty bed, albeit, one with bedsheets containing a man’s sweat.

The Crazy American Writer

Date and location of meeting: New York, NY, October 2016

I finally made it to New York (just for a short holiday). It was my last night in NYC and I was out with my girlfriend J, at her favourite Italian restaurant in West Village, L’Artusi. We walked in around 9pm on a Saturday evening without a reservation and were told it would be a wait of an hour and 45 minutes. As we walked in, we saw two men look over at us. After being told the wait, J and I discussed whether we should stay there or not, and decided we would wait and get drinks while we waited.

A few people were seated at the restaurant, and we moved up in the line. J went to go get drinks, and shortly after she was gone, one of the men turned to me and commented that wasn’t it ridiculous that there was a long wait for the bar? I remarked that it was, and he began talking about what a good restaurant it was. His name was John, and he was 35, and a former investment banker and writer for a well known financial review but was now working on a non-fiction novel and had his own PR company. He had previously lived in London, Singapore and Japan, and spoke Japanese, like me. I found him exciting and was surprised that we had things in common. I liked the sound of his voice and his offhand American charm. He was dressed in chinos, a blue pin-stripe button up shirt, and a khaki vest.Soon his friend came back and he introduced me to him- Matt, who worked at a hedge fund. I found M cuter, but M started talking to J when she got back, so our pairings were obvious. As we continued talking, our conversation started and stopped. I felt like he was either nervous, or uninterested. Eventually John and Matt got called for their table, and they said they would see us later. Shortly after that, J and I got called for our table. We ended up sitting at the end of bar diagonal from them, so we could see them while we were eating, but at a distance.

J and I had a perfect meal, and finished up and walked outside. I was messaging the guy I was meant to go on a Tinder date with that evening and J said she was going home, when John and Matt walked outside and asked if we wanted to get drinks down the street. My Tinder date hadn’t replied, so I thought ‘why the hell not’ and asked J if she wanted to go, while she exchanged a look with me that said she didn’t really want to but would go for my sake.

While we were walking to the bar, John turned to us and said his place was right there, and would we mind if he quickly ran up to get some cigarettes. I said it was fine, and Matt, J and I stood downstairs and waited for him. He took a lot longer than someone should to get cigarettes. When he came back down, we continued walking to the bar and chatting.

We got to the bar, which was on the same block, and they ordered a round of drinks. John was talking about how great the bartender was, and how he would make us great cocktails. This was the point at which I began to think he was a little odd.

He told me various things throughout the night, such as, “you’re a sweetheart”, “I feel comfortable with you like I haven’t with anyone,” as well as quoting lines from The Great Gatsby exactly WORD FOR WORD without looking it up, I kid you not, saying things like, “and so we beat on, boats against the current, borne ceaselessly into the past..” etc.

We had had a few drinks, and then John decided to order oysters for the both of us- so there we were, eating oysters at 2am, while he talked about how nice it was, and continued to say flattering things to me. The things he was saying were getting repetitive, and as I gazed into his eyes, I realised his pupils were huge. He was also sniffing a ridiculous amount. I realised that he must be on coke, and that the run up to his apartment wasn’t for cigarettes. At one point, he asked if he could kiss me on the cheek before he went to the bathroom, and I allowed him to. Around this time, the things he was saying were also getting a bit repetitive. I mentioned to J that I thought my guy was crazy, to which she said, he just seemed a bit odd.

When he returned from the bathroom, my suspicions about him doing coke were confirmed when he asked me to go for a quick walk around the block, which I assumed was to cool down. We walked quickly around the block, chatting, and while we walked, he told me he had a rooftop at his place and could take me to see it. I said sure, and when we walked back into the bar, I asked J if she wanted to come back to John’s place for a bit. I could tell that she didn’t want to go but just went along with it because I wanted to.

While we were walking back to his place, which was on the same street, John mentioned something about how he indulged in drugs “occasionally”, and I replied, laughing (probably hysterically) that I knew he had done some coke that night, and John said he would give me some. While we were walking back to his place, he mentioned he had a female friend, Madeleine, staying with him who was going through a divorce, and she had all her stuff all over his place. I thought this was kind of weird, or that this person must be lacking some kind of decency. We got back to his place, on the same street that the bar and restaurant had been on in West Village. J and Matt sat in the living room chatting, while John took me upstairs to the roof. Sure, there was a rooftop, but there wasn’t a great view.

While we were on the rooftop, I was strolling around inebriated, enjoying the breeze, when he took my face in his hands and kissed me. We stayed like that for a few moments, kissing on the roof, until I managed to disentangle myself and said I wanted to go back downstairs. When we came back into his apartment, J was gone and Matt was sitting alone. I asked him where she went, and he said, “home.” Feeling uncomfortable that she was gone, I recall trying to leave, but John saying everything was okay and that I should stay. He said something to Matt, which I don’t remember, but after he said it, Matt got up and left. I thought he looked irritated but in my drunken state, I couldn’t be sure.

As soon as he left, John went to another room and pulled out the coke. He had a small bag of it, and placed it on the table. I was about to tip it out to line it up, but he said he would do it for me, and stuck his finger into the bag, and then placed some in each of my nostrils consecutively. It was a small amount, but it was strong, and in no time, I was shaking and my eyes were wobbling. We sat down on the hard seat that J and Matt had been sitting on before, and he asked me if I wanted a drink. He only had beer, which I accepted and began sipping on. As we sat there, drinking beer in his apartment, I put on Talking Heads ‘This must be the place’, and we sat there discussing the meaning of the song. We talked about how it was such a great song, and I said it was about someone who’s never been in love before and who is guessing they must be in love from what they know about it.

At that point, I must have been expressing myself in an opinionated way as I was shaking from the bumps of coke. I started to feel sick to my stomach so I rushed to the bathroom to vomit, and was in there for less than five minutes when John followed me and knocked on the door asking if he could come in. I said yes, and then he came in and asked if I was alright and stroked my hair. I said, “I want to go home, I feel sick.” He said, “stay, I just want to spend more time with you since you’re leaving tomorrow.” I came out of the bathroom and again said I was going home. John walked into the bedroom and stood slightly past the doorway, and said, “just stay, we don’t have that much time left together. I don’t want to do anything. I’ll take care of you.” The things he was saying were ridiculously corny, and no one I had ever met on the first night had ever spoken to me like that. Nevertheless, I liked it.

We went to sleep spooning, with him holding me. I fell asleep almost straight away, and true to his word, he didn’t try anything.

The next morning, I woke up very early to the sun streaming in through the windows, and him holding me in his arms. I said something about how could he sleep without curtains, and he said he normally didn’t have a problem. We lay there talking for a couple of hours. Even in sobriety, he continued to say ridiculously corny things to me, such as, “you’re so thoughtful and genuine. So different to other girls. And you like cool music like Talking Heads. I wish I met you earlier. I’m going to miss you when you go back to Sydney. I wish you didn’t have to go back. We’re going to stay in contact. I’ll come visit you in Sydney.” And so on, and so forth. I didn’t think he was being genuine, but I played along anyway. And then the things got even more ridiculous. He said, “I want to do new things with you. Have you been skiing?” When I said no, he would teach me how to ski when I came back to NYC. And he didn’t stop there. He said he would take me to the south, to Charleston when I came back, and that I would I love the food there. I found all the things he was saying so unbelievable and nonsensical that I half wondered if he was going to ask me to marry him, the things he was saying just seemed to increase in absurdity.

I was on my side, facing the wall, and he was spooning me from behind. During the night, he had removed his pants, so he was just in underwear and his shirt, slightly unbuttoned. All my clothes were still on, and he slightly tilted my head to his side and kissed me. I pulled away first every time he did this, half because I wasn’t that attracted to him, and half because I had morning breath. I made the excuse that I didn’t want to kiss because I hadn’t brushed my teeth, and he said, “I don’t mind, but brush your teeth, if that’s what it’ll take for you to kiss me.” So we went to the bathroom and both brushed our teeth using the same toothbrush (he only had one).

We went back to cuddle in bed, and kiss a bit, and I could feel his erection pressing into my back the entire time. He said, “I’m sorry, I hope I’m not being too forward.” I replied, “I don’t sleep with people the first time I meet them.” He replied, “I know. I guess I’ll just have to wait.” I tried to creep out, more than once after this, and I said a variety of things, “I’m super tired and have to pack, I don’t want to miss my flight,” etc. but he insisted on taking me to lunch that day, “to spend more time with me”. Eventually I agreed, and we lay in bed cuddling for couple of hours, chatting about ourselves, and stuff like our past relationships and favourite books.

However, in the light of the day, I saw things that hadn’t been so obvious the previous night.

There were several pairs of shoes strewn around his bedroom, and more than one handbag. There was also a picture of two girls on the mirror. “If your friend is staying in the other room, why would she put all her stuff in here as well?” I actually strongly suspected that he was hiding the fact that he lived with his girlfriend, but I didn’t want to accuse him outright. He replied, “I don’t know, she just did. “So who is that in the picture?” I asked. He said, “Madeleine, and her friend.”

Not satisfied with the answers he was giving me, I went to the living room while he was in the bathroom and continued looking around. There were letters on the table, with a woman’s name on that address. There was an ID on the table that also matched her address. “Why do you have this person’s stuff?” I asked him, in an accusatory manner. He said something like, “I told you my friend was staying here, I don’t know whose stuff that is.” And while he was saying it, he had a crestfallen look on his face, so much so that I pitied him, and still went out to lunch with him.

We walked to a nearby Italian restaurant called Morindi, and were seated immediately. As soon as we were seated, he said again how sad he was that I was leaving, and that he was going to miss me. He then asked, “how should stay in touch, email?”

“I have Whatsapp,” I replied, and with that, we exchanged numbers. He texted me ‘hey there’ right then, and I saw his full name pop up. I kind of liked him at this point, despite his shadiness, but I still thought he was a liar. He asked me when was a good time to visit Sydney, and I said if he liked beaches, probably December or January. He even asked if there were tickets available around a thousand dollars, and I said probably. Although I would have liked to see him visit me, I found it highly dubious. At this point, I was wondering if he did really indeed like me, or if he was a master of deceit. He even took photos of me while we were eating!

After we finished lunch, I reached for my wallet, but he said, “Don’t worry about it – it’s our first date.”

After lunch, I was thinking of getting the subway back to FiDi but decided to book a VIA instead. It wasn’t to arrive for another 15 minutes though. While we waited, we stood on the street corner in the sun, chatting. He would lean in intermittently to kiss me as we waited. When the car came, he gave me a quick hug and kissed me goodbye. Before 20 minutes had passed, he texted me saying, “have a smooth flight, pretty girl”. I replied “thanks, it was great meeting you :)”, a few hours later, or the next day. He didn’t reply.

I had pleasant thoughts of him going home, and the next day, I landed in Sydney and went straight back to work. I immediately experienced the onset of post holiday depression and decided to Google him for fun. I had seen his full name flash when he had messaged me on Whatsapp. When I googled him, I was surprised to see that he had a Wikipedia page, and unpleasantly surprised to find a nasty article about him.

The article said he had hit a girl with a beer bottle (more than once!) at a club in NYC after the girl had rejected him and that she was suing. I was so horrified to read this I kept the article open and continuously searched him while at work the next couple of days in some sort of shell shock. The article said the girl was suing him, and the club, whose bouncers reportedly helped him escape before the police came. Another article I read said he was on “medication” when he hit the girl.

To add to this, I also found pictures of him in 2013 with the girl whose name I had seen on the letters to his address, which really irritated me. So basically, I spent the night with a violent drug addict, and very possibly used his girlfriend’s (?) toothbrush. But oh well, life starts over again when it gets crisp in the fall…

The British Guy

Date and location of meeting: April, Sydney 2016

Despite the name of the blog stating otherwise, I am not only on Tinder. I happen to alternate between using 3-4 dating apps when I feel like it, and The British Guy happened to be a rare find that I matched with Hinge, Coffee Meets Bagel, and Tinder. We matched on Hinge in late 2015 or early 2016, and Coffee Meets Bagel shortly after. While matching on Coffee Meets Bagel, we exchanged a few messages and planned to meet up once we both got back to Sydney.

Alas these things often go by the wayside, and when I got back to Sydney we had both forgotten about meeting up. As usual, I got caught up in the dating scene in Sydney, which kept me busy, in addition to the Private School Boy dramas. Around this time was the first time Private School Boy and I stopped seeing each other. I didn’t waste any time in jumping back on the Tinder horse and scheduling a date. We met up on a Sunday afternoon on the Easter long weekend, and I almost cancelled the date because I had a bender the evening before and was exhausted.

I had messaged British Guy the morning of our meeting (we had initially planned to meet at 1pm) saying I had had a bender, and could we possibly reschedule. He replied that we could postpone to a later time, and advised me to get some rest because “it is imperative that we bring our best versions of ourselves”. So I went back to bed for a bit (but failed to get any sleep), and then when I got up and started getting ready to meet British Guy, I all of a sudden got texts and calls from Private School Boy asking me to ‘come over and hold him because he was a mess.’ About four days earlier he had broken it off with me, and although I had been upset, I promptly got back on the Tinder horse. I messaged him saying I already started seeing other people again, and he messaged back saying he understood. However, as soon as I got his reply and was faced with the possibility of never seeing Private School Boy again, I knew that was the only thing I wanted. I was ready to cancel my date and head straight over to his place, so I messaged him again and said I could still come over if he wanted, but didn’t get a reply. So with that, I continued getting ready (dejectedly) for my date with British Guy, and then headed out to the city to meet him.

We had planned a day drinking session at Opera bar, and as I was arriving there, British Guy texted me saying he hoped I was wearing a distinctive red hat. I was standing near the bar, when a tall man with blondish brown hair approached me. He was tall, and had James Dean slicked back hair, and an attractive, masculine face with a strong jaw. I don’t remember what he greeted me with, but I found him very attractive and hilarious to boot.

We grabbed a drink at the bar before looking for seats outside. It was crowded outside, and there were literally no spare tables. As we searched for a table, British Guy joked to me that we should just sit down at a table with randoms and see what would ensue. The smirk on his face suggested he would be totally game for it if I was. Game for it though, I was not. So we ended up sitting on the stone bench facing one another, and chatting.

British Guy broke the ice with a question about roommate horror stories, and I said I didn’t have any roommate horror stories because I still lived with family, but my grandma blasting buddhist mantras at 5am every morning was technically one. British Guy told me worse stories about his ex-roommates, and had me laughing nonstop. He was in his late 20s, worked in tech, and traveled a few times a year. He was from somewhere in the south in the UK, and had been living in Sydney for a few years. Leading on from our roommate discussion, I told him I might have roommate horror stories of my own, as I was contemplating moving to New York in 2017. I confessed my indecision about moving, and that I had based my decision around two things- if I got a decent job here, and if I was dating anyone seriously. British Guy set a date for me to decide, which was 1st August, and said if I wasn’t dating anyone by then, to decide on moving, and stick to it. He even got out his phone and made a date in his calendar, to call me on August 1st to make sure I had made my decision and that I would stick to it.

We had one or two more drinks at Opera Bar, which British Guy picked up the bill for. For our next bar, we decided to hit up Palmer & Co in CBD, which I had never been to before. When we got into Palmer & Co, British Guy suggested a game involving the two of us selecting drinks for one another. If we selected drinks that the other didn’t like, we would take it as a sign that we weren’t a match and leave immediately.

We had a very sexy South American cocktail waitress who British Guy chatted to enthusiastically, and I wasn’t sure if it was because he was interested in her. He let her in on our game, and then after she had taken our drink orders, he dared me to ask her a questions (it might have been her name, or where she was from). I didn’t end up asking it, and so he did. They engaged in a short conversation, which seriously made me wonder if he was just very extroverted, or whether he was hitting on her. Shortly after, she brought our drinks out, and neither of us particularly liked our drinks, but we continued drinking them anyway, and sitting there. Neither of us made a move to leave, and British Guy commented on my not having left, despite it. With that, he said he assumed I was enjoying his company, and suggested moving onto dinner. However, he said he hadn’t anticipated the chill and said he would have to swing by his place and get his jacket if we were going to continue going out further. He said his place was within 20 minutes walk. I didn’t say no to this but had heard similar lines before and wondered if he was trying to hook up.

As we were settling up the bill, British Guy asked me to split. He said it was “the norm” that people split bills on dates, and commented that I was just selfish, with a smirk on his face, so I assumed he was joking. After paying the bill, I excused myself to go to the bathroom and at that moment, Private School Boy called me, 6 hours after I had texted him back saying I could come over, and said he was coming to pick me up right then. I told him where I was, and said goodbye and walked out of Palmer & Co with British Guy. We were standing outside on the street, when he was saying we should start heading in the direction of his place, and I said, sorry I was actually going to go home.

Just at that minute, Private School Boy pulled up, and British Guy, said “oh, this is you?” in a tone, and with an expression I can only describe as crestfallen. I said, “I’ll message you,” feeling guilty (for once in my life), and British Guy said, “no you won’t.”

And so we said goodbye, and I hopped into Private School Boy’s car.

Two months later, Private School Boy and I were out at dinner, and saw British Guy also lining up for the same restaurant we were waiting for. He was also on a date. We made eye contact, and he grimaced at me.

The Private School Boy Saga (Part Two)

13th April – end of April 2016

I felt things were going well with PSB despite my doubts. On Wednesday, we made plans to see each other, and I came over his house. We had intense sex that night, and fell asleep watching a movie. That weekend, we had planned to go hiking on Saturday and I messaged him in the morning asking which route he wanted to do. When he replied, I sensed a tone of distance: “Just got up, pretty exhausted. Don’t feel like doing anything today, Mum’s situation is changing, heading to see her and won’t see her again for quite some time.”

I knew his mother was seriously ill, and so I should’ve been understanding, but I won’t lie, I was fuming because he had just cancelled plans the week before. So I replied, feigning concern and masking my anger, and asked if it was okay, and said I hoped it would get better if it wasn’t. He replied a few hours later, saying it wasn’t going to get better. I was out having drinks for a friend’s birthday at the time, and decided not to reply until the next day. The next day, while lying hungover in bed, I texted him saying I’d like to be there for him, if he wanted me to. I waited all day, and didn’t get a reply, nor did I get one the next day. As you know, I’m no stranger to the waiting-for-a-text-back-from-tinder-boy game, and after the second day I assumed it was over between us. On the fourth day, he messaged me, saying: “I can’t see you anymore, I’m sorry.” I was out eating dinner with my brother when I got the message, and tried to stop a tear from rolling down my cheek.

I was upset, but didn’t let it faze me. I promptly threw myself back into dating life, and even had two dates that weekend. That weekend was a long weekend, and four days after he had messaged me the goodbye text, I was getting ready for a date, when I got a text message by PSB saying: “I’m a mess, come hold me please.” He texted again promptly saying “I know I’m being unfair but I’m so down, and I need you.” Then he texted again, saying “Please come?” After the three texts, I also got two calls from him right after that I ignored. I felt slightly triumphant that he had asked for me back, but I also felt like he had had his chance already. I took a hot shower after the messages and mulled over my reply. When I got out of the shower, I replied to his message and said that I had taken him seriously when he said he couldn’t see me anymore, and that I had started going on dates again. He replied promptly, and said he understood, and good luck with everything. After I got that reply from him, I realised that I only wanted a little more persistence from him. I then texted him back and asked if he was okay, and said I could still come over. I waited 20 minutes and didn’t get a reply from him, so I finished getting ready and went on my date.

My date and I were three or four hours into our date and had already hit up two bars, and were five drinks deep when PSB called me and said he was coming to pick me up. 10 minutes later, my date and I were standing outside the bar, about to head to another one (I hadn’t told him I was leaving) then as PSB pulled up, my date said “Oh.. this is you?” and I replied yes, guiltily. To mitigate the fact that I was leaving with another man, I said, “I’ll message you.” He turned back with what I can only say was a hurt look, and said, “No, you won’t.” It was one of my top 5 most awkward date endings. Despite that, I was very happy to see PSB.

As he pulled up, and I got into the car, he said sorry, he didn’t know I was on a date, and that it must have been awkward. I was quite drunk after the five drinks, and I said unabashedly that it would have been more awkward for both of them rather than me. PSB said the situation with his mother had gotten worse, but didn’t elaborate, and asked if I would be able to stay the week at his place. I graciously agreed, and so off we went on the long drive home to my house from the city to grab a week’s worth of clothes. After grabbing clothes from my place, we went grocery shopping and then cooked dinner at his place. While we were eating dinner, PSB said he had made up his mind to ask me to be his girlfriend, and asked me to stay during the week so that I could have some time to decide.

We had a relaxing night in, and the next morning he drove me to work, kissed me goodbye and told me to have a great day. It felt like we were a married couple. After work the next evening, I came back to his house. He had a piano lesson, with a female tutor who looked at me intriguingly when he introduced me as his “friend”, which I didn’t mind.

The next morning, he drove me to work again, and after work we had sex twice, went grocery shopping and cooked dinner. After dinner, we were lying in bed cuddling and talking about the kind of relationship that we wanted. PSB very clearly stated that he wanted a thin, pretty, Asian girl, who was on the pill to be his girlfriend. There were some things he said that could have been relevant to me (such as ‘likes puns’), but the majority of his requirements were by and large applicable to girls other than me. He also said during this time, that if I wanted things to progress, I would have to lose weight and be on the pill.

You got that right: he actually said “lose weight”. I’m sure any other sane girl in my situation would have abruptly ended it, but because I am insane I brushed it off. That night we had more #realtalk, which resulted in him singing “Fly me to the moon” to me before we fell asleep.

The next morning, he gave me keys to his apartment as he would be home late that night. I love getting keys to a boy’s apartment more than anything, so I was elated when he did so. I ate dinner out that night, then came back to PSB’s place and chilled. He came home shortly after me, and we chatted for a bit before falling asleep. That night we had a slightly tense discussion. We were lying in bed, when PSB said he really enjoyed this week with me, and was sad that we wouldn’t be having them anymore. I replied, “what do you mean we won’t be having these weeks anymore? You asked me to be your girlfriend earlier, in the week, is that not something you want anymore?” He said “I still want that, but I assumed you didn’t because of your reaction when I said you’d have to be on the pill, and you started talking about personal freedom”. At this point, I still really liked him despite all the lose weight talk. He said this week had been as much about me deciding if I wanted to date him as well, and that it would be selfish of him to ask me to be exclusive while I was still deciding. He said he would give me some time to think about it. I went to sleep feeling quite troubled about the whole thing.

The next morning, I took all my stuff to work, and said I would drop it at home after work then come back out for drinks, and PSB said I could leave my stuff at his place, then he could come pick me up after my friend’s birthday drinks and then drive me home, which I said no to. That night, when I saw my friends at dinner, I told them about the situation and they plainly said I shouldn’t be seeing him. I told them I intended to stop seeing him after that night and would break it off without a goodbye.

That night, he picked me up after my friend’s birthday, and we chatted before going to bed. I felt uneasy and a bit sad about my planned end with him, but didn’t mention it, and went to sleep. The next morning, I had plans with a girlfriend in Bondi, which he dropped me off to. While driving there, we passed a golf course, and I mentioned that I’d like to try playing sometime. He said he would find his mother’s golf clubs to take me at some point, and told me to have a good day and kissed me goodbye when he dropped me off.

That was even more troubling, as I was mentally preparing myself to say goodbye to him. That day, I told my girlfriend about the weight loss thing, and she clearly said I wasn’t fat, and that I shouldn’t be seeing someone who would ask me to lose weight. Later on that evening, I went to spend the evening with another male friend, and it was at this point that I realised I had left my makeup bag at PSB’s house, which I was extremely irritated about. I called him that night with the intention of asking him to drop it off to me right then, but he sounded funny, and so we said goodbye with me soliciting a promise from him to drop my makeup bag off to me tomorrow.

The next day, PSB met me in the city with my makeup bag. When he saw me, he kissed me hello and asked what I was doing then, and as I wasn’t doing anything, he offered to drive me home, and I accepted. When we got to my place, he kissed me goodbye and we made plans to see each other in a few days. I felt extremely conflicted about the situation.

The Private School Boy Saga (Part One)

After our movie date, Private School Boy and I had scheduled a date for the Sunday of the Easter long weekend, but on Thursday he texted me and said he was free to hang out Friday if I was. I said I had plans but would still see him Sunday. When Easter Sunday rolled around, I was having lunch with a friend in the city and when I finished, PSB came to pick me up in the city, and we went back to his place to have a movie marathon.

When we got back to his place, we were lying on the bed and cuddling and were only 20-30 minutes through some sci-fi film when he leaned towards me and started kissing me, which led to a makeout session. It wasn’t long before his hand was down my pants and pulling them off, which totally contradicted what he’d said a few days earlier about taking it slow if I wanted to. The first time, I rebuffed him and we went back to watching the movie, until maybe an hour later, he tried again and this time we kissed passionately for a long time, before he successfully took off my pants, took off his and started trying to slip it in. Long story short, we ended up having sex. During this time, he said, “I think I like you more than I should.” I replied, “I like you too.”

We were chatting and kissing later on, and PSB said: “I feel like it’s too soon to ask you to be my girlfriend, but will you be exclusive with me?” I said yes. While we were having sex the first time, I put his hand around my throat, and after we finished, he said: “I didn’t know you were into that. So hot,” with an interested expression on his face. We had sex several times that day, and PSB showed his nervousness, maybe the third time, when he went soft, and said: “I’m sorry, I’m nervous,” and pulled out, trembling. I found his nervousness completely endearing, and in the bluish light of his room, we just held each other and talked. We had just finished having sex at one point, and PSB came out of the bathroom to see me lying on the bed naked. He said: “you’re gorgeous,” as he inspected every inch of my body. We had pizza and watched movies that night, and fell asleep intertwined. The next day, we went grocery shopping and cooked a late breakfast together, and at night, he drove me home. We made plans to see each other a few days later.

Two days later, after my first day of work at my new job, PSB and I had planned to have a night in, and he was supposed to cook me dinner. I had requested that he cook potato latkes, and he had previously said that he would check with his mother how to make them, but that day I had gotten a weird text from him saying his mum would be out of touch for a few weeks, and that he would try to get it right on his own. I called him after work, and PSB said he had cut himself while trying to open a cooking utensil with a jack knife, and might possibly need to go hospital, if it was still bleeding by the time I got there. I thought he was exaggerating, but when I got to his place, his finger was still bleeding, so I accompanied him to the hospital although he said he could drop me off to go home. When we got to the hospital, I’m sickened to say we acted like one of those shameless couples who do PDA’s in public. We were waiting in the emergency ward, when he got a message on his phone, and I glanced over. I was sure that it was the Tinder symbol, and PSB excused himself to go to the bathroom. When he came back, he was chatting like normal, but I was barely speaking or giving him one word answers because I was suspicious about what was going on. He noticed immediately that my demeanor had changed, and began asking what was wrong (he probably also felt guilty). I asked him who messaged him just then, and PSB replied, “a girl called Lyn, from high school.” I replied, “oh,” and paused before saying, “I thought I saw the Tinder symbol on your phone.” And then he said: “It was. I never deleted Tinder.” You can imagine the annoyance and fury I felt when he said this, considering that he had asked me to see him exclusively just a few days before. I had deleted all my apps straight away.

At this point, I turned my body away from him, and stopped talking, while he fussed over me and tried to get me to talk to him. After a little while, I asked him if he was seeing anybody else, and PSB replied: “No, I asked you to be exclusive because I don’t believe you can develop feelings for one person if you’re seeing several people.” I then replied, through clenched teeth: “I don’t mind if you’re seeing other people, but don’t ask me to see you exclusively if you are.” PSB replied, “I’m not seeing anyone else. I just kept Tinder because it would take too long to make another profile if you suddenly stopped decided to stop talking to me.” I replied that it didn’t take that long to make a Tinder profile, when he said that it did. We spent a long time not talking then, until we got admitted to the emergency room, and PSB apologised again for messing up our night, and said that I was free to leave if I wanted, and he could give me his keys to go to bed early and rest for work the next day. I said that was okay, and watched his features soften, and he said: “I’m glad you’re here, thanks for staying with me.” While he was on the hospital bed, looking helpless and feeble, he said: “Tell me something you haven’t told anyone.” I said something nonsensical to deflect, and then asked him what he had done that day. PSB replied: “It’s a bit personal,” and then paused. I have to admit I felt like he was trying to take the attention off the fact that he was still on Tinder, but listened. PSB continued, saying that he didn’t have a good day, because his mother had attempted suicide. This was a lot to swallow given that we hadn’t been seeing each other very long. He said he hadn’t told anybody else about it, and didn’t know who to talk to about it. Shortly after, he got his finger x-rayed and then stitched up, and we left the hospital and went home. When we got home, I pretended to be normal despite feeling a little troubled, and we went to bed.

The next morning, he woke up early and cooked me pancakes for breakfast, and dropped me at the station. That weekend, I had plans to go to the Gold Coast with friends, leaving Friday night and coming back on Sunday night, so PSB graciously offered to pick me up from the airport. On Friday, he texted me saying he was going to miss me a lot that weekend. But then the weekend came, I went to the Gold Coast, and I didn’t hear from him. I thought about him all weekend, and regretted my travel plans, because I missed him so much. Later that night, when I got in to Sydney, PSB was waiting at the airport for me, and I saw him before he saw me. He was on his phone, texting, and when he looked up, he smiled, and maybe it was my imagination, but I thought he looked slightly guilty. I wondered if he was messaging someone on Tinder right then, and I can only imagine I threw him the stink eye. I was a bit icy to him afterwards, and we didn’t have the most comfortable of nights. When we got back to his place, I took a shower, and after I came out, he said, “talk to me”. I replied, “about what?” in an irritated tone. He murmured something equally irritated in reply, and I realised I was being unkind and changed immediately. We cuddled for a bit, and he asked if I missed him that weekend. I said “yes,” leaving out the fact that I had thought only about him that weekend. He said he missed me a lot, and he “wrote so many texts that he didn’t send”. I asked him why he wouldn’t send them, and he said he didn’t want to be clingy because I was on a trip. I found this behaviour wildly adorable.

The next morning, he woke up and cooked me pancakes for breakfast and dropped me at the station, and asked to see me on Friday night. That Friday, I caught a ferry to where his parents lived, and we went grocery shopping. While on the way to the grocery store, I told him about my desire to lose weight, and PSB seemed interested. I can only describe his reaction to my statement that I wanted to lose weight, as ‘restrained enthusiasm’. PSB said “what made you suddenly want to lose weight?” And then, as an afterthought, he said, “well I guess it doesn’t help that you’ve been hanging out with me, as I have 0% body fat”. I kid you not, he said that. Anyway, we discussed it a little further, and as we were grocery shopping that night, I had a strong craving for some kinds of cheese. The grocery store we were in at the time also had a great deli selection of gourmet cheeses that aren’t available at my local place.

Anyway, I tried to grab cheese THREE¬† TIMES, but PSB pulled me away every time. On the way back to his parent’s place, he told me that cheese would have been a terrible choice if I want to lose weight. When we got back to his place, he gave me a tour of the house and showed me all the rooms, as well as explaining all the family photos. No kidding, his parents’ house looked like it came out of an Ikea catalogue. His kitchen cabinets were also full of cookbooks (that they actually use), and one of the drawers was entirely dedicated to spices, and was alphabetically organised. After that, he cooked me dinner, and while he was cooking, he told me that he deleted Tinder. I was pleased at this of course, but not when I heard the reason.

PSB said: “I felt like we would get into a fight, if I didn’t delete it.” I replied, “you know I wouldn’t have said anything.”PSB said that I would have been passive aggressive about it, to which I said nothing (knowing it was true), but still felt uneasy that it hadn’t been a genuine reason for deleting Tinder. We had a relaxing night in, with dinner and a movie and sex on the living room sofa, before going to bed. The next morning, PSB had to do some work, but dropped me off in the city and asked if I wanted to come back over that night after my outing with my friends, which I agreed to. That day, I saw my girlfriends for lunch and dinner, then during dinner, I was about to leave to go back to PSB’s place shortly, when I got a text from him saying sorry, but he had a ton of work, and did he mind if we cancelled tonight. I acted chill and nonchalant, but really inside I was fuming. Later that night when I got home, he messaged me on Facebook saying he missed me and asking if I had a webcam. I replied coolly, saying that I did, but my Mac could crash anytime. He didn’t reply.

The next night, he called me at 10pm, and basically talked non-stop about his ex, but also said to me that he would be fine with me talking to guys from Tinder that are now friends (God knows I have so many of those) but that it would be a problem if I was talking to any of my exes. We chatted for a bit, and then said goodbye on a good note, but the conversation had left me wondering if he was actually over his ex.


The Perfect Gentleman

Location and date of meeting: Sydney, June 2016

*Refers to title* such a thing doesn’t exist right? Well, I was wrong.

I matched with The Perfect Gentleman in June, and he gave me a fairly standard greeting: “Hey there- pleased to meet you.”I assumed he was being sarcastic (but later on realised this is actually how he speaks), so I responded generically also. We exchanged a few messages back and forth before I got bored and stopped replying. Not long had passed, when Perfect Gentleman double messaged: “Hey, you should talk to me more. I like you.”

I found this utterly adorable, and started messaging him again. The next morning, I woke up to see that he had found me on Facebook, and we messaged each other back and forth a bit. That day was a Monday, and as I was heading to the gym on my lunch break, Perfect Gentleman asked me whereabouts in the city I worked. I said I worked near Martin Place, and he said he worked in Chifley Tower. This ended up being a serendipitous coincidence, as I work right next to Chifley Tower. Perfect Gentleman then asked if I wanted to go for a quick walk with him, but I couldn’t skip the gym, so we made plans to meet up on Tuesday night instead.

We exchanged back and forth messages all that afternoon and also leading up to night, when he messaged me saying he had a “surprise” for me, and would tell me about it on Tuesday morning. PG said it would only take five minutes, so of course I went to bed curious about what kind of surprise would only take five minutes. The next morning he sent me a good morning message, and I asked what the surprise was. PG said he was going to bring me coffee as I had been tired on Monday. I got in to work a little earlier than him, and as he got in after me, he messaged me when he was downstairs in my building.

I spotted him immediately once I came down. He was dressed in a suit, and had beautiful naturally tousled dark brown hair that I wanted to run my fingers through, and hazel eyes that crinkled in the corners as he gazed at me. He was so charming and handsome that I lost my nerve and as he handed me my coffee, all I could say was thanks, and make small talk about our respective office buildings as I looked up at him adoringly. We only chatted briefly for about five minutes or so, before we both went back to work. Shortly after I messaged him saying thanks for the coffee, and he asked if I was still up for dinner that night. Of course, I said yes. I was convinced I had met my future husband.

That night, he finished work around 5:45pm and met me in Martin Place. When he greeted me, he said I had a mischievous expression on my face, to which I said, I always had one on my face. PG asked what I’d like to have for dinner, and I said, I didn’t mind, and he said he could go “anywhere I liked”. I asked him where he’d like to go, and he said he felt like ramen, so I took him to Menya for dinner. PG ordered for us, and paid the bill. He was like a classic, old school gentleman, opening doors and pulling out chairs for me. We did the usual first date chit chat over dinner, and I found myself liking him more and more. PG was 28, and worked as an analyst in capital markets, but before that he had been a university teacher. Despite being 28, he had the face of an early 20 year old with a gorgeous boyish charm and a dazzling smile. He was the quintessential Prince Charming.

After we’d finished eating, we sat there chatting a little bit more, until I put on my coat, and PG asked if I wanted to get out of there. We walked out of Menya, and then as we walked, he asked if I wanted to get a drink somewhere. I suggested Baxter Inn, and off we went. PG always walked on the side of traffic, “so a car would hit him first”, he said, which was another one of the endearing things he did throughout the evening.

When we got to the bar, PG would always go to the bar and order, and leave me at the table. There was a candle at the table, which I used to warm my hands. When PG got back, he asked if I was cold, and grasped one of my hands to warm it up. Literally everything he did was adorable.

We had three drinks at Baxter Inn (three and a half for me, because I didn’t like one, and PG said not to finish it if I didn’t like it), before we decided to call it a night. During the night, we had discussed our favourite movies, and PG said Inherent Vice was one of his favourite movies. I said I’d like to watch it, and PG said he would bring it for me next time. We left the bar shortly after, and we chatted on the train platform. Our trains got in at about the same time, and he gave me a hug and a kiss on the cheek, and told me to message him when I got home.

He messaged me before I even got home, saying he’d had fun and we should do it again. We chatted a little bit back and forth before I went to bed that night. The next day and the day after, he sent me good morning messages as usual, and asked if I wanted to grab an afternoon coffee on Thursday. That day, I wasn’t at work and told him so, in addition to lamenting the lost opportunity to see him again. The next day, I didn’t get a good morning text from him.

The following week, I was walking across the street to go to the gym on my lunch break, when I heard someone say “hey”. I turned around and saw PG, who was getting takeaway lunch from a cafe across the street from my office. He asked where I was going, and if I had had lunch, and I replied that I had, and that I was going to the gym. He said he would walk me to the corner, and we chatted pleasantly until then. He told me he had been busy at work, but would message me. I didn’t hear from him again.