Let this story be some food for thought for all you 20-somethings navigating your respective new cities and postgrad purgatories, trying to walk the line between dating and hooking up.
I was out with some friends on a Friday night after work, and we eventually wound up at a somewhat overpriced but pretty chill rooftop bar in Midtown. The setting made it fairly easy to talk to those around you, and while the end of my night got a little hazy, I ended up getting the number of one of the girls I was talking to. We made plans to grab drinks sometime that next weekend.
Side note: I’ve grown to love first dates, which might seem strange to some, but I thrive off the awkwardness, butterflies and excitement that comes with actually getting to know someone for the first time. Call me crazy, call me a pussy… but you are what you eat.
That Monday after, one of my buddies at work and I are mulling over our weekends, and I mentioned how I was taking this girl out Saturday night and was trying to figure out a plan. He, being two years older than me and more experienced in the city’s dating game, recommended a restaurant and bar that he would usually take girls out to for his first dates. It was a little uptown and far away from where this girl lived, but he swore by it.
Saturday night comes, I pick her up from her place, and we take a cab uptown to said restaurant. The ride was between 10-15 mins which allowed for some mildly flirtatious small talk and remarks from her that she had never really been this far uptown but was excited about it none the less.
We get to the restaurant, which was a small, reasonably priced, very authentic Italian place with outdoor seating, and the waiters spoke more Italian than English. I ordered a bottle of wine and a cheese plate appetizer to snack on while we waited for the pizza to be ready. The conversation was flowing well, and I could tell we were both excited for the rest of the evening.
Next came the bar located about two blocks from the restaurant. This place was quiet and laid back (by bar standards) with some solid cocktail choices and lounge-like seating that made it easy to have an intimate conversation. The conversation continued to go well, and I started to get the feeling this night wasn’t going to end with just a kiss goodbye at her front door.
We walked a little further to one more bar (this one improvised by me and not part of the original plan), and after one more drink, she mentioned that all of her roommates were at a concert that night and that I should come back to her place and see the view of the city. We hopped in a cab and headed back downtown to her place where she poured us both a drink and took me up to the roof. The view was actually really spectacular, and after a minor amount of talking, we started making out. Then we made the move down to her bedroom.
This is where things started getting heated, clothes coming off and everything. Once we were both just about naked I mentioned to her that I didn’t have a condom. I asked if she had one, to which replied she didn’t, but said I could put it in anyway.
Now I know what most of you are thinking: why didn’t you just go for it? What’s the worst that could happen? Well, with my number of sexual partners creeping up into the twenties, I have become a firm believer that one night of fun is not worth 18 years of child support or a lifetime of herpes. So much to our dissatisfaction, we didn’t go any further.
I did end up staying the night, and the morning after wasn’t really that awkward either. About a week later I texted her back and we made plans again to get dinner after work. The second date was a good time, but I think we could both tell it wasn’t really going anywhere. After a few more texts and Snapchats, we stopped talking altogether. While I’m sure we would both be game for a “what r u up to?” text on some random drunken night, the possibility of this becoming a relationship is zero.
Moral of the story: if you’re taking a girl out for the first time, put in the effort to make it fun. But also, bring a damn condom (unless you get a thrill from playing STD roulette). If the night goes well, and she’s really into you, she probably won’t want to sleep with you right away, but then again she’s none the wiser about that extra heat you were packing. If she enjoys the date, but doesn’t think you two have a future together, at least you have something more than just the bill for dinner..
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