How do I flirt with someone who’s really into, well, partying?

We’ve been friendly and flirtatious from the get-go. I, as somebody who prefers to tell people, “I’m not into club kids,” this guy makes me nervous. While he doesn’t make me feel too young (he’s done all his partying right around my age) or scary (most 18-year-olds don’t bother me), I realize that he’s 20, a college student, and has a myriad of young friends to show for it, so I guess I need more than a chance at flirting to feel comfortable.

On this date, I really wanted to make it out to a nice restaurant with a cute drink. I loved everything about the restaurant—it felt fun, chic, and trendy—so I was hoping that we’d get more than a second look from someone with more than $10 in his pocket, and end up at a spot that we could get service to ease our desire for the company of our own friends. After all, when are 18-year-olds allowed to go out with their friends?

The two of us locked eyes in the waiting room as we waited to be seated. Within seconds, I realized that we were actually sitting right next to each other and if I didn’t make a move, he would.

“You’re wearing a dress, right?” I asked.

He didn’t look offended. “Well, okay,” he said, “I do wear dresses.” It was obvious he only wears them to feel other people up, not for potential dates. I smiled, but there was a part of me that wanted to run away.

I was comforted to know that we were in the same bar, so I asked to sit next to him, but before I could, he awkwardly asked to slide into my seat. He was pretty uncomfortable as I talked to him about my love for New York City and my latest mood-altering brain-painting projects. I’m looking for someone who is able to embrace being himself and not fake it.

On the way out, the bartender asked me how many drinks I wanted, so I had to decide if he’d be sitting next to me at a bar or at a restaurant that would be OK if I just got three drinks, which is less than one’s dinner count. I chose the bar because I have a little more left on the credit card, and I’m also fine with my date having three drinks because we are doing it out of kindness and to make his (and my) night more enjoyable.

I took my time and ordered a Cabernet Sauvignon. It was good.

“Do you want fries with that?” he asked.

“I’m not going to have them with dinner,” I said, disappointed.

“I’m not going to do anything to make yours ruin your night,” he replied.

He gave me the cold shoulder for the rest of the ride home, but all the while, my date was a cutie. He asked about my day, offered to take me to a movie on his off days and was appreciative of the arrangement.

I’m still in awe of the way he handled the situation and didn’t, in any way, try to turn it into an awkward dinner date. It’s interesting to see if he thinks the way I did, and what I do when one of my dates stops by the table (which happens about a quarter of the time) seems frivolous. It really makes me doubt that the age difference is real (though some people are just too dang in love).

I’m not looking for a relationship, but I wouldn’t mind having a little fun and some fun company. I have a bar back at my house, so I could have a drink or two with my date, depending on what I ordered. The next time I am with a 20-year-old, I might have a drink as well.

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