Tips For Dating Someone 10+ Years Older: Don't

The scene is this: I’m 26 years old, he’s 35. He begs me to come over and spend the night, even though I already saw him two other nights this week. It’s late, but I cave and take the multiple subways it takes me to get there (surely he doesn’t offer an Uber, even though he completely demanded this nighttime hangout). I arrive, and he’s shoving a Sweetgreen salad into his mouth when he casually mentions, “By the way, I have a call with the London office at 3am, so I’ll just go into the living room”. So you basically just want someone to hang out in your bed all night while you’re on a work call? What am I, a labradoodle? 

Before we head to bed, he says, “So what’re you gonna do at 3am?” Oh, silly me! He wants me to leave in the middle of the night. “I’ll see,” my people-pleasing self says (the side of myself that only comes out around guys like this). Cut to 3am, and his alarm wakes me up. I go to the bathroom and come back half-naked, glasses on, hair a mess. He says again, “So what’re you gonna do now?” Guess I’m leaving! I put on my clothes, walk to the subway and head home. It’s raining. Since you asked, no, he didn’t offer an Uber this time either. 

Clearly, the above guy is the ultimate worst, no matter his age. However, I think we can all agree that this sending-a-girl-home-in-the-middle-of-the-night-type behavior is especially unacceptable for a 35-year-old man. Through the years, I’ve unfortunately come to terms with the fact that a giant age gap is just not it. So, what is it about these boys…I mean, men… that are still single at an older age and going for younger women? Here’s what I think, based on my personal experiences:

Option A: He’s Insecure

Now that I’m far older and far wiser (okay, three-ish years older but with a hell of a lot more dating experiences), I can clearly see that the guy who sent me home via the subway in the middle of the night was debilitatingly insecure. He wasn’t confident enough to date someone who would hold him to any kind of standard (or doesn’t want to be held to any standard), even if that standard was just basic human decency. He is smart, though! He went for the younger, new-to-New York gal who was easily love bombed into falling for him and later into accepting his disrespectful behavior. 

There’s a specific type of insecure bro who craves a certain power. He wants someone who will automatically be impressed by him, and an age gap allows for that. As someone who was once the Vulnerable Younger Girl, I can understand why we’re a pretty easy target. The Vulnerable Younger Girl wants to feel “cool” at that age—and how cool is it that you’re the lucky chosen one that the older finance bro with the sweet apartment is texting? It feels almost impossible to give up—so we don’t. 

Option B: He’s Not Looking For Anything Serious

New scene: I’m 25 and at the club (you know, normal things 25-year-olds do). A guy comes up to me asks me my name and how old I am. I say I’m 25, and he says he’s 35 (less normal). We start grinding and making out. I hadn’t even done the ol’ fashion dance floor grind/makeout combo since college, and I was the young one. I gave him my number. He texted me the very next morning asking when we could go on a date, and I immediately felt ~soooo~ stressed out and guilty that this 35-year-old was probably looking for something super serious, like a wife! (This was my first time meeting an older bro, can you tell?) I accepted his invitation for a date. Once I got to know him better over a few more dates, I grew to really like and respect him. But, of course, it was then that he admitted he was not looking for anything serious. Ah, the classic Peter Pan.

This Peter Pan simply does not want anything from you other than a fun hang and casual sex. Your young age makes him feel less guilty about his revulsion for monogamy and communication. You don’t have marriage on your mind, and you haven’t started thinking about your biological clock just yet. You’re a breath of fresh air—until he realizes Vulnerable Younger Girls eventually want relationships and commitment, too. Once he realizes this, his good time is done, and he ghosts you.

Option C: He Hasn’t Worked On Himself

If you’re 39, keep interrupting me when I speak, and get into conflicts with wait staff wherever we go—you might be single because you don’t have any awareness of who you are and what it is that’s preventing you from being a strong partner in a relationship. (Totally not referencing anyone specific…) 

I’m not a man, but I’m guessing that men have the privilege of time because of biological reasons. A woman who is 29 might be more eager to make relationships and settling down a priority in her life, and thus realize the work she has to do to get there (therapy, self-help literature, introspection) earlier on. On the other hand, a man might not have the desire (or the pressure) to begin the same self-work until many years later. Yet, what many don’t realize is that you can’t automatically be in a relationship just because you’ve decided you finally want one. Take the totally fabricated 39-year-old I was referencing: he didn’t start taking dating seriously until he was 37. He has a lot to learn before anyone dares to commit to him. You know, if he were real and all. 


I’m sure there are some kind, consistent older bros out there. I just personally haven’t met them. If you’re going to date an older bro, the one piece of advice that I’ve had to learn the hard way is to watch out for red flags more so than you usually might. Ask him why he’s single (without any judgment in your voice—keep it classy), and let him take the lead. He knows how to pursue a woman at this point, so if he isn’t being consistent, he’s not going to actually date you. And remember, just because he’s had a lot more time to build a life for himself than you’ve had does not make him cool! It makes him old.

Images: Studio Firma /

Sydney Kaplan
Sydney Kaplan
Sydney Kaplan is a fashion creative and copywriter, and most importantly super relieved she doesn't have to write an annoying, corporate bio for her freelance writing gig at Betches. She's based in NYC and previously lived in San Francisco, and through her travels has learned she prefers finance bros to tech nerds. You can follow her on all social media at @sydneyrekaps.