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Why dating in your 30s is hard

Posted on Monday, August 29, 2011 in dating, Kat, Men, Relationships, Women

As Sara and I browsed the Union Street boutiques searching for the perfect Little Black Dress for her niece’s wedding in a few weeks, we couldn’t help but overhear two attractive 30-something blondes nearby. Their conversation sounded eerily familiar to ones Sara and I had had ourselves not too long ago.

“I swear, I just don’t get dating anymore. It’s impossible to be what guys are looking for. You’re screwed if you’re too direct because then you’re come off as cold. If you’re too aloof, you’ll seem like a bitch but if you’re too eager then you’re too needy,” one lamented.

“You’re so right.”

“Plus, you can’t talk about your ex-boyfriends because you’ll sound bitter, but you can’t talk about the future either because then it’s like you’re fishing around for commitment or something,” she continued.     

“It’s nothing like when we were in our 20s!”

“But, we’re not even old!”

“I know but it feels like it. Like that guy I went out with last week, you know? When I told him I was 34, it was like I could see him doing the baby momma math on me — ‘Well, if we start dating now, then get engaged and married, it will be about two or three years and we’ll have to have a baby right away because she’ll be too old and I’m not ready yet.’ It’s depressing!”

Wow — even I was getting depressed listening to them! Now, when Sara and I were bemoaning dating post-divorce, we were in our 40s, fresh out 15-year marriages, and moms. We were not baby-making machines anymore. We already had kids, and most of the guys who were interested in dating us were mostly divorced and had kids, too; the guys our age who didn’t were looking for younger women, not us (well, except for a hookup). Coordinating custody schedules was challenging, and single parenting and working full time was exhausting!

Still, I remember thinking how much easier it might be to find love again if I had gotten divorced in my 30s, not my 40s. Listening to the blondes, however, I’m realizing that may not be the case.

But, the young blonde (yes, 34 is young!) was right — once you’re out of your 20s, dating is an entirely different beast. Dating in your 30s gets a lot more complicated because of kids — either you have them, which limits your dating ability; you don’t have them but you want them, which puts you on a tight time-track for fertility; you don’t have them and you don’t want them, but you may have to reject a lot of good guys who do want to have kids; or you have them and you want more of them, which, again, means you may be facing fertility issues.

Whoever said kids put a strain on a marriage has no idea how hard it is to date with or without kids as a 30-something!

All of which means — you better enjoy dating in your 20s because if will never be as carefree and fun or offer as many options again! Ever. OK, that’s not fair; I had fun dating post-divorce and, after all, I met Sean in my mid-40s and that’s been very great. A few of my middle-aged friends have met great guys and women, too (although none has remarried). But, let’s face it — dating when you’re older is really, really different, especially if you’re looking for a relationship and not just casual sex. And sometimes, it downright sucks.

What’s your dating story at your age?

Photo © Angelika Bentin –

Bring on the comments

  1. brian says:

    didn’t finish college, grad school and law school until i was 29 so sorta outta sync
    last thing i wanted was to settle down
    spent my 30’s living my lost 20’s
    travel and starting a career
    also at that age no way i wanted the burden of another man’s child although my views changed a lot thru my 30’s
    by the time i’m late 30’s the options were biological clock’s which made me feel like an interchangeable part to the woman’s goal
    any guy with money and a sperm donor just fulfill your role of provider
    love appeared to have little to do with it
    while i was looking for the last grand love of my life
    came to appreciate the single mom with kids much more
    jugling work, being often a single parent and at times still pursuing their dream of finally completing their college education
    problem there often was time and/or childrens jealousy or even fear of loosing time with their only parent to a strange man
    as the kids grew older less of a concern
    recall one of the nicest comment i ever got was from a woman with preteen daughters who said of all the guys mom had dated when they started dating they wanted a boyfriend like me

  2. Kat Wilder says:

    #Dating in your #thirties? Good luck!

  3. Kat Wilder says:

    #Dating is easy in your #20s, challenging in your #40s but is it hardest in your #30s? Yes because of #kids!

  4. Rhonda Shrum says:

    #Dating is easy in your #20s, challenging in your #40s but is it hardest in your #30s? Yes because of #kids!

  5. Kat Wilder says:

    Brian — so, what happened??? No marriage and babies for you after all? This comment makes me sad, though, “any guy with money and a sperm donor just fulfill your role of provider
    love appeared to have little to do with it” Really?

  6. Travis Blunt says:

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