Dating: Your 20’s VS Your 30’s

"I've been dating since I was 15, I'm exhausted!! Where is he!?" - Charolette York


Written By: Stacey Teller & Katie Tetz

Two girls. Same problem. Is dating in your thirties all that different than dating in your twenties?

“I’ve been dating since I was 15, I’m exhausted!! Where is he?!” -Charlotte York

Truer words have never been spoken. I have been dating for two decades and have yet to meet my prince charming. I may however have fucked up a few potentials and been screwed over once or twice along the way. Still, this does not deter me from my endless search for my bearded, active, tall, kind, professional who wants kids, likes country music, and wants to travel.

Too much?

Even though we can make the same mistakes in any decade of our lives, our 20’s and 30’s have some definite differences in terms of dating mishaps, or at least in how we handle them.

That’s what my friends and I tell each other anyways. Usually over a few bottles of red.

Here are some of the major differences I’ve noticed as a thirty-something navigating the dating world.

Twenty-something year old you: “I can’t sleep with him! What if he think’s I’m a slut? Blue balls for everyone!”

Thirty-something year old you: “I can sleep with whoever I want, whenever I want, however often I want.”

Your 20’s and texting:

Let’s play the I-am-not-interested-game. I will call or text, only when he does first. But in the meantime I will check my phone every 15 seconds. Even if it means taking 10 bathroom breaks at work before noon, just so I can check my phone and reread all of our conversations.

Your 30’s and texting:

I don’t need a text or a call from a man to validate my greatness. I will text you first because I have zero interest in games. This will quickly show me if I’m wasting my time.

20’s: The Ex Factor.

I will stalk your Facebook, Instagram, Twitter, and any other social media platform you have available. If you block me, chances are I will figure out the password. And for the record, your new girlfriend isn’t as cool as me.

30’s: Another one bites the dust. 

“Can’t be bothered and good luck to the next one!”

 20’s: Let’s Make Excuses!

“I know he has potential. When he grows up a little bit, it will all be fine. He just needs some time and allllll of my patience.”

30’s: Buck up Buddy.

“I am not your mother. Figure your shit out.”


I understand if he still talks to his ex or flirts with girls at the bar. It’s part of who he is. I trust him. But I will go on a full blown investigation and search his phone like a crazy women, searching for any signs of inappropriate texts or numbers/names I don’t recognize.


No. Not okay.

20’s: Get white girl wasted on date 1 through 4.

30’s: There is such a thing as getting elegantly wasted on red wine. It just takes an entire decade to master it.

20’s: Daddy Issues.

“Oh, you have kids?” Radio silence.

30’s: We still have Daddy Issues.

“Oh, you have kids?” Aw I bet he is such a good dad. He has his priorities straight. Great husband material!! [Insert emoji with heart eyes].

20’s: On taking a break:

“We are just on a break; I can’t date anyone else. He just needs some time…”

30’s: There’s no such thing:

“Break? That’s code for breakup! The world is my oyster…”

20’s: The friend factor.

“He wants me to meet his friends!!! This is cause for celebration!”


“He wants me to meet his friends. I really hope I haven’t slept with any of them…”

20’s: In summary.

He has a great job, he’s smart, he’s kind, and he’s really into me. So let me see how I can screw this up and go for the emotionally unavailable instead!

30’s: In summary.

Same as above, but you actually think twice about it. You’ll even get advice from your friends over wine, coffee, or post yoga brunches, only to come to the same conclusion.

Bring on the emotionally unavailable!

Come on ladies, there is a reason we are still single, and it is only 99.9% the male species fault. 😉

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