Is Dating Younger a Big Deal?


Real quick.  What are your thoughts on dating younger?  I’m knocking on 29, and I’ve just not been able to make it work with guys my age.  I tried dating older, and that didn’t work out for me.  The older men I’ve dated always came into the situation like they were the authoritarian and I needed to be schooled in everything.  Anyway, I met this guy at a bar about two weeks ago, and we’ve been texting since then.  Only problem is that he just turned 21 a month ago. From what I know he seems cool, but that age difference makes me nervous.  What do you think I should do?
-Young but Not that Young

Dear Young but Not that Young,

Thanks for writing to me.   This is a dilemma many folks go through, regardless of their sexuality.  They have gone out with a few dudes among their “type,” so they try dating outside the box to see if they will have more success in love.  And I always encourage doing that.  Heck I’ve done it.  You never know the “type you want” versus the “type you need” until you get out your comfort zone.

Having said that, if you’re clicking with this 21 year old, then stick with him and see where it goes.  I understand he’s not in the particular age range that you’re used to, but he’s legal.  And he can go into all bars and clubs you may frequent.  If you’re like me, your apprehension about dating younger boils down really to a maturity issue.  Which is an understandable concern.  But if after two weeks of talking and he seems alright, give this guy the benefit of the doubt.  He may be more mature than some of the men you’ve dated that are your age or older quiet as it’s kept.

Now if things don’t work out with this guy, don’t use the experience to write off all younger men.  Just think of it as a bad experience with this particular younger man.  Also, if it doesn’t work out with this 21 year old, reevaluate how you are as a dater. It’s possible that you are having a hard time dating because you are a bit of a problematic dater.  If you aren’t sure what that is, make sure you check out my blog piece about it (Problematic Dater).  Additionally, reexamine where you meet men.  The guys for you may not frequent the places or apps you visit.

Suggestions going forward.

  1. History has proven that for some people, younger works. Need I mention Jay Z and Beyoncé?  Or Angelina Jolie and Brad Pitt? So “don’t play yourself” and miss out on a possible good thing.
  1. If you are going to give this guy a shot, then give him a real shot. Don’t go into this situation looking for things about him to nitpick just so you can discredit him because of his age.

As always nothing but love,


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