Question:

I’ll be 30 in a few months and met a girl where I work who is about to turn 21 . Some friends say she’s too young for me. How young is too young for someone my age to date?- T., NYC, Facebook

I really can’t answer that without knowing either of you and what you’re looking for.

Here’s my take: If you’re a reasonably attractive guy in Manhattan, have a decent personality and have your shit together, then you should be able to find someone closer to your age. If the best you can do is someone that young, then I have to wonder why. What is it about that particular person that you are drawn to when you’re surrounded by a bevvy of smart, intelligent, beautiful women closer to your age? If you’re not able to find someone a little older, there’s a reason for that. I don’t know what it is, but there’s something about someone that young that appeals to you.

Maybe women your age intimidate you, or maybe you don’t bring enough to the table to be able to sustain something with a woman your age. Maybe you aren’t ready for anything serious and would prefer to be with someone who is. Not sure. But with an age disparity like that, there are deeper issues at work. At least, I think they’re are.

At 29/30, I’d say the youngest you should go is 24/25. Something changes at that age. We’ve had  a few years to date in the real world, not college dating, which is a whole different animal. We’ve begun to or are well on our way to developing an identity and sense of self. Before that, certainly at 20 or 21, we just don’t have that. I think having that sense of self is crucial for both parties. Up to that point we’re kind of feeling our way around in the dark, discovering what we want, like and who we are.

I can remember a girl in college having  a much older boyfriend. He’d occasionally pick her up at the dorm or drop by our sorority parties. The few times he’d interact with us he’d make condescending comments, as if we were so silly for partying in a bar at 21.  My take on him was that he enjoyed having this “above it all” attitude. That was something he probably wouldn’t have if he were mingling amongst his peers. I think what appealed to him about my friend was that she was young and impressionable and a tad precocious. Dating an “older guy” made her feel impressive. The situation just had this “ick” factor about it. Even at 20, 21 or 22 some of us would wonder why he wasn’t dating someone his own age. He’d look odd and out of place at parties. But she was happy. She’d come to our sorority meetings and chat about where he took her for dinner and his apartment and his job. At 20 or 21, that stuff was impressive, as we didn’t have that. Someone older probably did and thus required more in terms of substance and accomplishment.

It’s different when you’re older. A 37-40 year old man dating a 27 year old doesn’t seem nearly as out of place. Or at least it doesn’t seem like he’s taking advantage of her naivete. I think that’s what rubs me the wrong way about the OP’s situation. There’s something predatory about someone his age dating someone that young.  Other factors play in to that feeling as well. Such as lifestyle, educational or career background. It makes me wonder of the older person uses such accomplishments  as a way to assert control or to gain admiration. Blind adoration.

So, that’s my take.

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