First Time For Everything: Dating A Younger Man

I have forever dated older men. Some by a year. Others by four years. Another by ten years. My theory came to be that ten years might be the ideal age difference. I felt five years older than my age, and men were usually about five maturity years younger than their actual age, so if I was 25, my ideal mate would be 35. We would meet at the figurative age of 30. It all made perfect mathematical sense. Several months ago, I found myself at a party. From across the room, I made eye contact with a man. He wore a permanently bemused expression, had a mop of curly hair, and a bit of mischief in his blue eyes. I leaned into my friend Sara and asked her of his origins. “That,” she told me raising a brow, “is Freddy. You will like him.”

Whenever someone says something like that, it inevitably puts ideas in your head. The idea that my industrious brain, working in conjunction with my sex-starved libido, had was that I was going to go home with Freddy. And when I get an idea in my head, well …

I went home with Freddy.

And let me tell you, Freddy kissed good. The sexual chemistry was very much there. You know when all you want is for a man to take charge? To throw you up against a wall and show you “Who’s the Boss?” a la Tony Danza? Well, Freddy totally Tony Danza’d me. And call me Alyssa Milano, but I liked it. I liked it a lot.

Pillow talk, as it usually does, ensued. I was pleasantly surprised that unlike most of the other men in Los Angeles, Freddy actually read books. Just like me. And he was funny. He told me the real problem with LA was that nobody acts their age. I laughed. And agreed. Indeed, it is disconcerting to look around a nightclub and find that most of your male counterparts are baby boomers.

“How old are you?” I asked Freddy, my head resting comfortably on his broad shoulder.

And that’s when things took a bit of turn. Because Freddy informed me that he was 22.

When I first found out that the Younger Guy was, well, younger, I was apopleptic. “Twenty-two?” I kept repeating. You’re “Twenty-two?” “Yup!” he replied eagerly. I felt as if I was in bed with Dennis the Menace. Weren’t there laws about this? Freddy did not seem at all bothered by the idea that I could be his older sister. He asked me what the big deal was. What had I really learned between the ages of 22 and 26? Had I become exponentially wiser? What was all that different about he and I?

I snorted internally. Only about 1460 days, I thought to myself. 1460 long, long days.

Instead, I answered that at 22 I was wide-eyed and bushy tailed. I had great hopes for my life. Now I understood that this was it. I had turned into a bitter old cynic.

What was wrong with all the girls his age anyway? Freddy replied that he liked me. I was smart and witty and pretty. Let me tell you, all it takes to get me in the sack is for someone to tell me that I’m pretty and I’m funny. (I never claimed to be hard to get). And Freddy did both of those things. Maybe he was wise beyond his years.

So, despite my world weary attitude, I though that I should give it a shot. I threw caution to Demi and thought — why not? Why not try the younger guy?

Freddy treated me as if I’d hung the moon myself. He made me feel confident. Unlike other men, he didn’t seem to shirk from my self-proclaimed status as a funny girl. He admired that I was a writer, pursuing a less traditional career path. He looked at me with these big worshippy blue eyes and I loved it. I loved every second of it.

He was energetic, eager to learn things, and very excitable — in at least two ways.

It was fun to be able to dole out advice to someone who sort of looked up to me. Show him the ropes, so to speak. But sometimes showing him the ropes wasn’t all that fun. And there was no one to talk about my ropes with. Advice, shall we say, was not his strong suit.

There was also the question of his younger friends. I enjoy long, boozy dinners at new restaurants. They enjoy long boozy nights watching “Fletch” and drinking forties. We did not exactly have common interests.

But there was still that whole Tony Danza in the bedroom thing, which I just couldn’t shake. Where did he learn all these things at the ripe young age of 22? It was impressive.

But Freddy wasn’t one for making plans. At first, his text messages were cute. Then the 11 p.m. booty call on a Monday night lost its cachet. I wanted someone who was my equal, who wanted to do the same things I did. For some reason, Freddy never needed to get up in the morning. I, on the other hand, had things to do.

I bid farewell to Freddy — amicably, of course. Sometimes I still swing by to sip a forty with him. But what I learned from Freddy was that everyone should try the younger guy — at least once.

Maybe twice.