Dating : How to Ask an Adult Out on a Date

In my junior year of high school, I took Mr. Bennett’s Economics class and had the good fortune to be seated one row away from a good looking kid named Todd.

I’d never taken a class with Todd before, but all it took was for me to spend a couple of weeks imagining what it would be like to kiss that guy, frequently glancing in his direction with those brain waves emanating from my cute sixteen-year-old face, and “Bam!” he asked me out.

Easy-peasy.

Another time, in college, I showed up at the Theta Chi house looking for a guy named Casey, whom I’d met at the softball game earlier that week. I was there when he told me to be. I was supposed to pick up a glove for a mutual friend, but really I thought he was sort of asking me out. Turns out he really wasn’t, or he would have been there. But one of his fraternity brothers didn’t pass up the opportunity, and we wound up dating for two years.

Now that I’m in my forties, though, it seems like the initial ask is the most difficult thing ever. It’s a lost art. On one level, I get it — most of us have been married, some for a long time, and we got used to only having a conversation with our partner for that whole length of time.

Along came Tinder, and that turned out to be a bizarre scene of bots and unreliable narrators and twenty-year-old photos and a nonsensical array of strangeness. I have a very cynical essay about Tinder if you care to take a look.

Then there’s the danger of asking someone out and they say no because they’re married. Or worse, they say yes and they’re married.

These are shark-infested waters.

But hear me out. The art of asking someone out on a date is not to be abandoned. It just has to be revived. Just this past summer, I had the best meet-cute ever, and we dated for a few months after. The actual act of asking me out was the most thrilling feeling. So if you are thinking about whether or not to do it — my sincere advice is: DO IT. Do it now. Do it right now!

Here’s how my summer asking out went; I kid you not:

This very handsome man interrupted me briefly on the street, doing his best to do so in a non-threatening way. He said, “Excuse me, I don’t mean to interrupt.”

And then he gave me a very kind smile. I was surprised, but charmed, because, as I said, he made sure to position himself in a way that worked to make me feel comfortable (so, yeah, fellas, you might want to practice this in a mirror or something if you want to try this out — and it is situationally unique, but you just never know…).

Then, he went on, “I just wanted to tell you that I saw you walking and I just wanted to tell you that your hair is just remarkable. It is really beautiful.”

Then he smiled. He just smiled, and didn’t ask or say anything or seem to want anything.

I just said, “Well, thank you! Oh my gosh, you made my day.”

Now, here’s where he could have been creepy, but wasn’t. If I was not single, I could just cross the street and be done with it. But I’m single, so I smiled and lingered and he smiled and lingered, and in the lingering, he offered his handshake and told me his name. A very simple, “I’m Eric, by the way.”

And I introduced myself, and in a flash, he said, “I would love to see you…and that hair…again sometime.”

And that is all it took.

Now imagine if you see a very pretty woman, and you think her hair is great, and that is all you think. “Gee, her hair is great.” And you do nothing else.

Let me tell you this much when it comes to asking an adult on a date –

We are all about it. I promise. I’ve Tindered and it’s not that great, but I sure miss the days of flirting with a guy in Econ class and instantly going out to the movies on Friday. That meetup this summer was the greatest thing since 11th grade.