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10 Things To Consider When You’re Dating A Woman In Her 20s

February 22, 2019

Let her be wild.

Photo by istock

So you’ve fallen for a fantastic woman in her twenties, have you, my sweet thirty-something lesbian? Falling into the golden arms of love and falling into the red hot lap of lust is a gorgeous, rare thing. So congratulations, babe. I get it. Women in the thick of their twenties are complicated, interesting creatures. And I personally think a difference in age can beautifully serve a relationship. I’ve always dated people outside my age range. I find a different perspective on life to be a wild turn-on.


Love and lust do not conquer all, even though I wish in the deepest pit of my heart that they did. All too often bullshit gets in the way of true love—like, for instance, an age difference. Age is not just a number. Yes, you can be unbelievably smart and mature and cultured for your age, but that doesn’t substitute for actual time spent on Earth. And when you have more years on another person, there are just some things you’ve gotten out of your system that are still growing inside of them—and bursting at the seams, begging to be released from the flesh cage.

You can let this drive you insane. You can let this lead to a dramatic, painful breakup. Or you can be mindful of your age-related differences and try to make it work. Because if it *is* love, and you do have electric chemistry with her, you must always try to make it work. It’s disrespectful the holy concept of love to walk away just because a relationship isn’t flawless. PSA: No relationship is flawless. If it’s not an age difference, it will be something else.

Here are nine very important things to keep in mind when you’re in your thirties and you’re dating someone in their twenties.

1. They are still HUNGRY to see the world. You must never deprive them of this hunger.

Once you’ve hit your thirties, you’ve got a good grasp on what you like and what you don’t like. If you don’t care for Chinese food, you won’t have a burning desire to hit up the trendy new Chinese restaurant in the Meatpacking District, will you? If you prefer lounges to dive bars, why the hell would you set your adult foot in a goddamn dive bar?

Women in their twenties are still figuring out what they like as they navigate the big, bad adult world for the first time. They want to see and try everything! Maybe you’ve been to Vegas a hundred times, but they are dying to experience the sins of the city. If this is the case, you must encourage them to go. Go with them. Embrace their lust for life and try to experience things you’ve already tried through their fresh eyes. You might even realize that you’re stuck in your ways and have written off so many things prematurely, anyway.

Depriving a twenty-something of experiencing the f*ck out of the world is cruel. It’s like clipping the wings of a beautiful butterfly. Don’t be a butterfly clipper. It’s bad karma.

2. You have to let them go out or they will resent the f*ck out of you.

You work hard and the last thing you want to do this Friday night is get wasted at a party teeming with twenty-somethings. But your girlfriend really, really, REALLY wants to go to the party. Let her go to the party.

You don’t have to go with her. Or you can go for one gross red-cup drink and let her stay out ’til 2 am because that’s what twenty-somethings are hardwired to do. Do not force them to adult with you on a Friday night if they want to be crazy with their peers. For they will harbor deep resentment toward you. And the moment you come across as a “parent” who doesn’t let them do what they want, your sex life will go to shit, and you’ll get stuck in a very unhealthy (but very common) dynamic: the parent/teen dynamic. Gag!

If you don’t trust them to go out without you, why are you dating them?

3. Love ’em, but leave ’em wild.

Love her but leave her wild, babe. Let her wear the slutty crop top. Let her wear the unpractical high heels that you just know are going to kill her poor feet in about two hours. Don’t say “I told you so” when she’s writhing in pain later, either. Smile and carry her shoes for her. She’s in her twenties! She’s a wild cat! Celebrate her wildness or date someone you’re own age.

4. They will have menial dramas. Try not to undermine them.

When she comes home from her waitressing job upset because some other bitch waitress made up a nasty rumor about her, do not—do not—make fun of her for having such petty problems. Don’t lecture her on “real problems.” I understand that you are dealing with big grownup things like your savings account and a giant promotion at work, and her little problems seem so stupid and trite to you.

But close your eyes.

Remember when you were in your twenties? Pettiness and unnecessary drama is simply a part of life in your 20s—and it sucks. Have empathy. Be grateful you’re no longer in a place in your life where you have so many immature squabbles—but support her through them. She’ll feel shitty about herself if you roll your eyes and discredit her feelings. And do you want to make the woman you love feel lousy? Unless you’re a narcissist, you don’t.

5. Don’t play the role of the mentor.

If she asks for advice, totally give it to her. But don’t become her goddamn mentor, who spearheads her entire career trajectory, OK? Be her lover, first. Don’t become her career consultant because once you do that, there will be a dangerous shift in power. She will feel like she needs your input to do anything. (You’re always looking for someone to tell you what the hell to do in your twenties because you’re so damn lost.) And that will stifle her growth. You’ll have too much of a say in her life, which will rob her of her power and make her feel like she’ll die without you. (I know it sounds dramatic, but it’s true. I’ve been on the receiving end of this many times.)

6. Let them make mistakes and figure shit out the hard way.

Do not rob someone of the experience of screwing up. Screwing up is so important because you learn unbelievable lessons when you screw up a big opportunity. You learn lessons on a visceral, guttural level—and it helps to shape you into a strong woman.

When you stop someone from making a mistake, you are snatching their power from them. They deserve to have these bad experiences so they can grow and learn and become better, more powerful people. I understand that it’s frustrating to watch a trainwreck from the sidelines when you just know so much better, but close your eyes and think back on your mistakes. Think of how vitally important they’ve been to your life. Think of the role they’ve played in your success.

Don’t mess around with their fate. Let fate f*ck with their fate.

7. Pay the bill, if you can.

This might be controversial, but I stand by it. If she is broke and young and working her ass off to make her rent, pay the bill. Most women are not users, by nature; that’s a lie the patriarchy has poisoned us with.

The fact of the matter is this: If you have a real grownup job that provides you with real money, and she is still deep in the struggle, the right thing to do is pay the bill. If you’re both broke (which can completely happen in your 30s!) get cute and start making dinner together.

8. Connect them, if you can.

If she’s an aspiring singer, and you happen to know someone who is a fierce talent agent, put her in touch with your career contact. Don’t get weird about it just because you’re romantically linked up. No one gets anywhere in life without connections, especially in New York or LA. Even if she ends up smashing your heart, you’ve done a good deed. And good deeds provide you with good energy, and good energy attracts you to good sh*t.

9. Build up their confidence… remember, it SUCKS.

Everyone in their twenties, regardless of what they say or how they behave, has horrendous confidence.

You might act like a cocky shit when you’re in your twenties, but inside you’re teeming with irrepressible bouts of imposter syndrome. Most women say they would never go back to their twenties because it’s such a mess, such a sh*t show. Remember how it felt to be in your twenties. Being your twenties is like walking around with a giant open wound that anything can get in and infect.

Do not tear your twenty-something girlfriend apart. Accept that you are dating someone who is in a very vulnerable place in their lives and work to build up their self-esteem. Otherwise, you’ll riddle them with issues that will bleed into their thirties and likely turn them in a wildly dysfunctional adult who needs loads and loads of therapy.

10. Don’t be shocked by a sudden change of heart.

Believe her when she says she loves you. She means it with every fiber of her being. But don’t be shocked if she has a sudden, drastic change of heart.

Things change very quickly in your twenties. Especially feelings. Wish her the best. And let her go. Don’t clutch onto resentment and curse her name to every lesbian in town. You knew what you were getting into when you decided to date a twenty-something, right?

And heartbreak will never kill us, anyway. Especially when we’re thirty-something adult women who have established, proper lives, and have learned to love ourselves without another person affirming us. Act like the grown-up I know you are. Good luck, babe.


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