They say December is the worst month of the year to match with someone on a dating app, and I experienced that firsthand last year.
First came Christmas, then he went on a remote trip in which he had no phone service for a week. And, when he came back to Chicago after the new year, I had to travel to Texas for my best friend’s wedding.
After three weeks of chatting, things fizzled out. We had a courtesy date, and that was that.
The time and effort spent on apps before meeting the person is a top complaint with modern dating. So this December I skipped the dating apps and took a different, old-school approach that got me four first dates: I went speed-dating.
The night started fine. I entered Tabu in Fulton Market, walked to the bar and ordered a strong cocktail called “The Devil Made Me Do It.” I felt so hot and mysterious, y’all. Then, a cute guy asked if I was there for the event, started conversing with me, and I confidently asked if I could scoot closer to him.
“Whoa, am I doing it? Am I getting to know people in a ‘natural’ setting?” I asked myself mid-scoot.
The scoot made me spill half the cocktail, but I didn’t sweat it. It might make me more memorable over the other guys. The cute guy, you see, also was there to speed-date. But more about him later.
I talked with friends, people I met at a bar last weekend and even the host of the speed-dating event, and here’s what I think would be most helpful if you’re considering speed-dating.
When to schedule a good speed date?
There were five of us attending that Wednesday night. When I was the odd one out, the host told me about the group sizes he’s seen: Weekdays tend to have smaller groups, while weekends are more packed.
With my small group, it was a great way to dip my toes into something new. But it’s up to you what you think you’re ready for. Start small, or dive right in to the variety of singles Chicago has to offer.
A good quick-date tip
We had six minutes, with a two-minute warning. It can be intimidating, especially if you’re with someone you really want to impress.
First, I wanted to know if the person could carry a conversation. A friend asked me later this common-sense question: Did you flirt? I could’ve done a better job of that.
If you feel a good emotional or sexual connection with someone, be sure to drop a hint that you’re interested. “I love your smile.” Or be even more direct with, “You’re very sexy.” Leave no room for doubt you’re open to seeing them again.
What if they don’t like you back?
Look, I paid $35 for this. So I wasn’t expecting an elaborate dating experience produced by Netflix or ABC with Chicago’s most eligible bachelors lined up to woo me.
But that’s the thing. You’ll want to set no expectations before going into this. And be open-minded about the people you’ll meet.
Maybe you’ll meet a goofy person who doesn’t know they could easily sex you if they asked, or an older person who owns property and could introduce you to your first mature relationship. Or maybe you’ll meet someone you never thought you’d be interested in but are really into.
I was able to get one match that night. The cute guy from the beginning, however, didn’t like me back. And I don’t blame him.
He asked me how my Thanksgiving went, and I talked about how I had trouble with my turkey being a little undercooked. “Oh, maybe your oven door was loose,” he suggested as he kindly entertained my story. By then, I was too deep into the narrative to figure out how to make it sexy or naturally transition to another topic.
I want to stay delusional and tell myself maybe there was a glitch in the system, or he filled out the online form wrong. But no. Midnight came and went, and so did any sort of future with him.
The next morning, I got a screwdriver and tightened the screws on my oven door. No more raw poultry stories on first dates for me. I’ve moved on from the rejection, and so should you.
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