They say that age is just a number. Well, whoever “they” is has clearly not been on many dates. There was a time when I was really frustrated dating guys in their 20s. None of them seem to have the attention span to keep a girlfriend. So I decided to give dating older guys a shot. And then I realized that they were just a little too old for me, a little too figured out. I would hear myself complain about it and I sounded like the Goldilocks of men’s ages. This one’s too old. This one’s too young. Does anyone have markers so I can make a sign saying, “Wanted: JUST RIGHT”?

I’ve even developed a test to measure a guy’s age to his maturity level. It started when I was on a sixth date with someone who was almost 9 years older than me. I liked everything about him. He was nice, smart, hard working, and our families had a lot in common, but I couldn’t put my finger on one thing. What did he do for fun? I finally asked him this very question and he without missing a beat goes, “I don’t really know.” How does a person not know what they do for fun? Seriously. And then I asked THE question. The most important question for me to determine just how much one can let loose, not give a damn, and just enjoy life.

Me: Okay… but when was the last time you had like a fun drunk karaoke night?
Him: (long, long pause) 1998.
Me: That was the last time you really had fun like that?
Him: (shrug) Yeah.

Do I even need to tell you that this was the last date? It wasn’t the karaoke thing that was the deal-breaker. It was the fact that it had been 14 years(!) since he had a let-your-hair-down-Facebook-picture-worthy night. FOURTEEN years! Titanic was still in theaters the last time he had fun. Britney Spears was still a virgin. There was no such thing as an iPhone. I had a Tama-freakin-gatchi. I mean, this was a long, long time ago. When was my last fun drunk karaoke night? Two weeks ago to the day. But I have fun nights where I find myself smiling as if I have a hanger stuck in my mouth pretty often. And that’s a requirement for any guy I date. I instantly knew it was time to reel in the gap and date guys closer to my own age, even if they might not be as ready for a relationship as I am. I want to find someone to grow up with, not grow into. That poor guy though. He will never know that he was just one Livin’ On a Prayer away from a Total Eclipse of The Heart.