I Went Speed Dating — Here’s How To NOT Fail Miserably

One Friday night last year, I went speed dating with a friend who asked me to go.

At first, I said no. (Then a coworker convinced me otherwise.)

$25 later, I was in.

The place was at a long, narrow bar in Little Tokyo where 15 women sat against the wall on separate tables and the guys would rotate around. Five minutes per conversation. At the end, the girls and guys would circle the people they like and, if there was a match, they would get each other’s contact info.

I wore a button-up shirt and jeans — if anyone cares to know — but I knew that was silly because I knew every other guy would wear that. (And they did.) In hindsight, I could’ve worn a hoodie under a blazer.

Oh well. It made zero difference.

How did I do? I guess I faired okay, but I wasn’t interested in most of them. One, I just circled for purely physical reasons, but during our text exchange, she said she lived in Diamond Bar and that’s, like, hella far.

Anywho, here are several important lessons I learned that night:

The most common question people started with was, “What do you do?”

Don’t ask that. It’s a terrible question to lead with and it doesn’t spark a good conversation because it’s so clichéd, boring, and similar to something you’d ask in an interview.

It’s also a waste of time. You only have five minutes to build some sort of connection — why waste it learning about the intricacies of medical supplies?

Well Anthony, what would you say besides this?

A lot.

First, let’s agree there are literally thousands of questions to ask someone besides this. So if this is the case, why is it so difficult to think of another, more-interesting question?

Is it fear? Tradition? Routine?

Would it be weird to ask a girl: “What’s your favorite thing to eat for breakfast?”

I don’t thing so. Food is better conversational topic than work. (And you can, like, totally make fun of her for still eating Cheerios.)

That’s just an example, of course.

Answer that question with care.

For a few girls, I answered with the truth. I said something like, “I’m a writer.”

I saw them perk up after that and I decided to stop saying it.

I learned that from comedy. Jerry Seinfeld, one of my favorite stand-up comedians, almost never swears. In one story about him, he tested a joke by adding a swear word. When he noticed that the dirtier version did better, he scrapped the entire joke.

He didn’t want to use a joke that wouldn’t have been funny without the expletive.

For me, I didn’t want them to be interested in me because of my occupation. I’d MUCH RATHER they liked me because I displayed an interesting personality, enjoyed their personality, and had fun.

For the rest of the girls, I answered with: “Well… what type of exercise do you do?”

Then we were off to the races.

There’s no such thing as awkward silences.

Inevitably, there’ll be a period where a topic stops and there’ll be silence.

That’s okay. That’s natural. Relax. Enjoy it. A lot of us, however, have an aversion to the dreaded awkward silence. Often, we feel that if this person is a great fit, the conversation should just go smoothly… otherwise it “wasn’t meant to be.”

That also ignores all the other outside factors. Sure, if someone doesn’t say anything, there’s an issue. But if there’s a few lulls in the conversation, so be it.

At one point, a girl got really insecure and looked at me like, “Well…?”

That’s okay, too. Character counts.

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Overall, it was an interesting experience. Even though I got zero dates out of it, it was still a good lesson and my friend and I had a nice time.