Date and location of meeting: December 2015, Sydney
What I wore: first date- camel coloured, oversized wool coat with maroon coloured diamond patterned dress with collar. Second date- white balloon dress with black wedges and gold chain choker
What he wore: v-neck shirt with slim jeans and pointy shoes, blazer. Second date- navy blue suit with light blue pinstripe button up shirt, Omega watch, pointy leather shoes.
I matched with the Investment Banker in late November 2015. I didn’t find him very attractive but swiped right more because of characteristics that reminded me of Voyeur Tinder. For example, they were both east Asian, both investment bankers, had both grown up in Western countries, and were now living the expat life in Asian countries (Investment Banker had been living in Hong Kong for 6 months, and was just back home for a brief business trip) and were even the same age. The Investment Banker started the conversation with a generic ‘hey’, and there was nothing that stood out in this greeting. We chatted back and forth a little bit, making small talk and trying to make plans but failing, as our schedules weren’t compatible.
We chatted back and forth, trying unsuccessfully to schedule a date. Investment Banker was originally from Sydney, but had moved to Hong Kong recently, and was just back home for the week. He expressed his desire about wanting to meet me so earnestly that I decided to make some time late on a Wednesday night after a Craigslist BDSM encounter with Proxie X (more on that later).
Investment Banker told me that he was staying at Four Seasons Hotel and to meet me at Grain Bar, which was just downstairs, and part of the hotel. In my experience, when a man from Tinder or other various online portals suggests to meet somewhere, it may be so that they can easily manoeuvre back to their place. Or that they are lazy. But because of the nature of what Tinder is used for, very often it’s the former.
So I went into the date, with my suspicions about what manoeuvres Investment Banker would try to make. Instead, I was pleasantly surprised. I waited for him in the lobby of Four Seasons Hotel, and saw him walking over to me. He waved and smiled, reminding me of the way Voyeur Tinder would smile at me.
We introduced ourselves and then walked a few feet over to Grain Bar. Investment Banker dressed nicely and spoke in a confident manner. He was also dominant and took the lead- basically an alpha male. We fell into an easy conversation and had one drink each at Grain Bar, which were charged to Investment Banker’s room bill. He said that I was the first girl he had met on Tinder, and that he had just recently gotten out of a long term relationship.
After having a drink here, Investment Banker suggested that we go to a different bar nearby.
We had one drink each there as well, he picked up the bill. I got fairly drunk that night as I had only had a light dinner, and he offered grabbing something to eat after two drinks, but I said it was getting late and that I should go home. He walked me to the station and we said a lingering goodbye, both of us looking at each other in the eye like we wanted to say more. At that point we both asked if the other was free again before we both had to fly out of Sydney and our schedules didn’t align. We hugged each other goodbye and he said thanks for sparing the time to see him.
I went home on the train in a haze and texted him straight after saying that I had a nice time and that I would have liked to see him again. I usually never do this after first dates but there was something about Investment Banker that reminded me so much about Voyeur Tinder, and I guess I wanted to be more upfront this time and see where it could go. He texted me back promptly saying the same, but it was a shame about our conflicting schedules. I was so tipsy and caught up in texting Investment Banker that night I forgot to get off at my stop and had to change trains at the next station. When I texted Investment Banker about my predicament, he said come back and crash at mine.
I don’t know if this was a booty call or out of genuine concern. I had been texting Tech Entrepreneur at the same time and had also gotten an offer to come over to his place. I was going to take up Tech Entrepreneur’s offer when my phone died, so instead I just went home.
The next day, Investment Banker texted me asking if I was still free Friday night. I replied saying that I was, and he said great, let’s have dinner and drinks. He had previously said that he was busy Friday night. I’d like to think that he cancelled his plans to go out with me.
We met at Central at 7pm on Friday night, and I was glad to see that he had dressed well. On our first date he had also dressed excellently as well. He had great taste and all his clothes looked expensive.
He picked a bar nearby to have drinks at before heading to the restaurant. Investment Banker had great taste in bars as well. We were in a hipster bar in Surry Hills that evening, and shortly after we had gotten drinks and sat down, he asked, out of the blue “were you spoilt as a child?”
I replied that I probably had been spoilt as a child and asked how he knew, to which Investment Banker smiled at and said that it seemed like I had received a lot of love and attention. And a lot of toys to boot. I asked him what the first thing that attracted him to a woman was, and he replied that he went for “the hottest girl he could find”. This lack of regard for personality honestly worried me a little.
After drinks, we walked to the restaurant and I was pleased with his choice. Investment Banker ordered crab for one of the courses. I’m a girl that loves to eat, so when the crab arrived, to say that I dug in and ate with my hands, sucking out the meat with my fingers like a savage would be an understatement. Investment Banker bared my unsophisticated dining habits without staring in horror, and I was extremely grateful for this. The food was delicious, and as expected, not cheap, but Investment Banker picked up the bill as usual.
He asked me what kind of men I was interested in, to which I replied that I was most attracted to older men, who were intelligent, humble and kind, preferably with some similar interests.
After this point, our conversation seemed to come to a push and pull, where both of us were trying to indirectly state what we wanted from the situation.
Investment Banker would say things like “I really want to be in a relationship with someone,” and I would say “but you live in Hong Kong,”. And he would say “yes, but I can basically come back anytime I want since most of my clients are here” (bet this was a big exaggeration). And so on and so forth.
After our last drink, we decided to call it a night and Investment Banker walked me to the station. We hugged each other awkwardly and kissed goodbye on the cheek, but never spoke again.