Date and location of meeting: December 2015, Sydney
What I wore: first date- flared white denim skirt, light blue button up shirt, black patent loafers. Second date- black suede wedges, leather pinafore dress, long-sleeved grey turtleneck
What he wore: first date- black v-neck t-shirt, soft draped black coat with pattern in PU black squares all over, black pants, black pointy shoes. Second date- black button up shirt, black jeans, colourful runners.
I matched with the Tech Entrepreneur in early December. While chatting, he said that I could Google his name to see if it was real (he had an unusual name that reminded me of ancient Roman times). When I did, I was surprised and impressed to see that he had a Wikipedia page AND a New York Times article written about him, in conjunction to other articles. We made plans to smoke shisha together on a Monday night, and he said he would pick me up in an Uber- I love when boys come from overseas and offer to pick me up not knowing how far away I live (I live 45 minutes out of the city).
Tech Entrepreneur is American, but lives in Singapore. He had come to Sydney for some conferences on math, but worked in Singapore doing something with startups and tech. His Wikipedia page had stated that he was a software developer and researcher.
When I got into the car, my parents had been walking outside the house and saw me getting into the car with an unknown boy in the backseat. They were throwing me looks like ‘WHERE DO YOU THINK YOU’RE GOING’ while I was throwing them back looks that said ‘I’M A BIG GIRL I CAN DO WHAT I WANT.’ Needless to say, I was glad to get away. Tech Entrepreneur greeted me like a friend and said that he had a present for me, which I was delighted by. He was also wearing an ostentatious get up that made him look like a villain from out of a Marvel comic book. His gift to me was part of a keyboard that he said was being developed. The piece had six buttons and he got me to go over them and see which feel I liked. When I said I liked the two buttons with a hard sort of click he said: “I knew you liked it hard.”
We chatted animatedly during the whole Uber trip, and Tech Entrepreneur said that he was going to the get Uber Black until he saw that I lived 40 minutes away and decided to get Uber X (the cheapest one). We had an interesting evening discussing our Tinder experiences as well as different cultures. He also gave me his business card, which was of a solid material, and listed his title as a ‘disruptive technologist’. Tinder has it all apparently- from venture capitalists to disruptive technologists, just take your pick.
I told Tech Entrepreneur about my indefinite plans to move to NYC or SF next year, and he said that SF was the place to go if I liked geeky white boys. He said “there are so many geeky white boys, you could line them up if you wanted”. The idea of this sounded very appealing to me.
While smoking shisha, I enjoyed engaging in #realtalk with Tech Entrepreneur, something I haven’t been able to do with anyone for awhile. After smoking, we went inside the cafe, and he ordered an omelette and specified that he wanted the bacon “extra crispy”. When the omelette arrived, Tech Entrepreneur looked at the bacon, proclaimed that it was not “extra crispy”, and proceeded to disdainfully remove the pieces from his omelette. During this time, Tech Entrepreneur asked if I liked horror movies, to which I said no. Then he said that he had a horror movie that he wanted to watch, but didn’t watch horror movies on his own.
He then asked if I would watch a sci-fi movie with him, since I liked sci-fi. I said that I probably wouldn’t come over, because I didn’t want to hook up. Tech Entrepreneur said that it was fine to come over without hooking up, but I decided to make a sensible decision (for once, LOL) and go home. Tech Entrepreneur dropped me home in the Uber, and I wasn’t expecting to hear from him again, but he texted me immediately after he had dropped me off saying I look forward to napping.
He had been saying earlier that it was probably a good idea that I didn’t come back to his place to hook up because he would be tired in his conference the next day.
The next day, I had a Craigslist date (a proper date, not for BDSM sex) with a Japanese man, and had told Tech Entrepreneur about it. After my dinner had finished, he texted me asking if I wanted to come over. I was actually going to come, only that he immediately texted me back saying that he was tired and was probably going to nap, so I went home instead.
We texted back and forth since we met. Tech Entrepreneur was hilarious, intelligent and I had great intellectually stimulating conversations with him. I loved his company, but I wasn’t attracted to him. I loved that he spoke to me like a friend and invited me everywhere he went, like to his pilates classes, and to eat random vegetarian meals (he is not a vegetarian by the way). I liked that he said dirty and outrageous things to me such as: you’re too cute to have a dry pussy. Despite texting every day since Monday, we didn’t get a chance to meet again until Thursday evening, which was completely by chance. I was having dinner with a friend in the city. It wasn’t too late when I finished, about 8:45pm, so I texted Tech Entrepreneur and asked if I could meet him. Tech Entrepreneur said he had a meeting with an Italian researcher in Newtown, but of course I could come, as long as I didn’t mind that they would be busy talking for about 30-45 minutes.
When I got to the pub in Newtown that they were at, Tech Entrepreneur introduced me to the researcher, and I got a drink while I was waiting for them to finish up, and sat next to him. Tech Entrepreneur had his Mac on the table and was engrossed in some sort of code, while also drawing symbols on a piece of a paper that I had no idea what signified. I was sitting there quietly, listening to the two of them discuss complex math, when Tech Entrepreneur turned to me and asked how my day was and expressed apology for not paying attention to me. He said he would chat to me while his coding was finishing, but clearly the Italian researcher did not hear this piece, and looked at us with irritation as Tech Entrepreneur chatted to me. It was TOTES like that scene from Pretty Woman when Richard Gere invites Julia Roberts to his business meeting, and is distracted by her the whole time, only that Tech Entrepreneur and the researcher were talking math, not mergers. After a few minutes of this, the Italian researcher couldn’t restrain his irritation anymore, and said that he was going to leave. Tech Entrepreneur apologised and said that he was just waiting for his code to finish, and they resumed talking and drawing symbols on paper.
Shortly after that, they finished up, and Tech Entrepreneur was able to give me his full attention. There were many things I liked about him, such as how he called me “cuteness” and would subtly hold me by the shoulders or waist, that he would get so engrossed in looking at me, much to the exasperation and irritation of waiters, bartenders and Italian researchers wherever we went.
We grabbed another drink, and we discussed how I seemed ‘conflicted’ by his vulgar statements- as in I found them hilarious but refrained from using such words myself, as in words to describe the female anatomy. With my permission, he also had fun going through my Tinder and trolling my new matches, asking if they were cut or uncut.
I had a few glasses of wine that night, and as is my habit when I drink alcohol, I didn’t want to be alone. Therefore, Tech Entrepreneur and I got an Uber to his place, but I (think) I made it clear that we weren’t going to hook up.
When we got to his guest house, we walked upstairs and went into his room. I would have been content to share a bed with him, but when I saw that there were two beds, I took one and got ready for bed. He asked me if I wanted to take a shower while he took a bath, or take a bath while he showered. Being prudish in front of men I hadn’t slept with, I said no, but hovered in the doorway a little chatting and watching him bathe. Tech Entrepreneur was not shy, and didn’t hesitate to strip down and take a bath in front of me, walk around naked, etc.
If I had any intentions of sleeping with him before, they were gone after I saw him bathe. There was something about his shriveled, pink penis that reminded me of a baby’s penis, and I found it extremely off-putting. After he bathed, I then took a bath, then prepared to go to bed. Due to the glasses of wine I had knocked back earlier in the evening though, I found myself getting up to vomit, not once, but numerous times. Tech Entrepreneur seemed worried by this, and said that he could “call an Uber for me to go home, and it would be okay.” I said that I’d stay and went back to bed. During this time, he was still up, coding or doing whatever it is that tech entrepreneurs do late at night. While I was trying to get to sleep, I heard him say “did you just come here because you had to stop off in the city? It’s okay if you did” (lol, I did). I did enjoy his company though.
I woke up the next morning to hear the Tech Entrepreneur saying “good morning” and that we were going to another hotel, because apparently we had been too noisy last night (we didn’t even hook up!) With that, I got ready quickly, Tech Entrepreneur packed his clothes, and we vamoosed out of there. But not without passing the middle-aged landlady on the way out, who gave me a look of deepest loathing. I couldn’t help smirking as I walked past her, and heard her say “yeah, it’s hilarious” as we exited the building where conversation was not allowed after 11pm.
After that, we walked across the road to grab a beverage. Tech Entrepreneur looked over the cakes and said “none of these are moving me”. To this, the older man who looked like he owned the cafe said “they’re cakes. They’re not meant to move you” while rolling his eyes. TE ordered an iced chai and said to the man “and whatever she wants”. After getting our drinks, TE paid and we sat down and chatted while waiting for our Uber.
After our Uber arrived, we got in it and went to the next hotel. TE remarked that it didn’t look like the sort of hotel where you’d be kicked out for conversing past 11pm. After dropping off his luggage, he had to go to the university, and I had a prior engagement, but lamented not being free to hang out with him more, as TE was so enthusiastic about wanting me to hang out with him at uni more. We said goodbye with a hug and I left, wondering if I would ever see him again.