Dating An Older Man: 5 Perks & 6 Pitfalls

Age gaps in relationships matter less to a lot of people these days — maybe because we see it play out so often, both among celebrities and everyday couples. Sure, a big age gap can create friction, including around sex with an older man, but these relationships can absolutely work if you go in aware of the likely upsides and downsides of dating someone older.

Here are some of the benefits of dating older:

1. More Experienced in Relationships

Older guys generally aren't into mind games. You won't spend time wondering whether to text an older guy back immediately, wait around, or agonize over what to say. He's more likely to just call you. And if he does text, it's not a strategy — it's probably to lock in plans to see you.

Related: How to have phone sex

Basically, an older man skips the games, and you shouldn't feel pressure to play hard to get either. He knows what he wants from the relationship and says so with confidence. He's willing to hash things out rather than leave you guessing why he's upset. If something's bothering you, speak up — older guys tend to prefer things laid out plainly.

2. More Mature

Older men generally handle their emotions better than younger guys tend to. They're more level-headed and think before reacting. They're less likely to get defensive or angry over feedback, unlike what can happen when dating a younger man.

That said, an older guy chasing a much younger woman might be doing so out of his own immaturity — maybe he can't connect with women his own age, or he's never really grown past his party days. Avoiding adulthood isn't exactly a great look.

3. He's Done Playing the Field

Dating older usually means fewer wild nights out clubbing together, but it also usually means he's moved past the phase of chasing constant novelty and checking his phone for the next hookup. Older men typically prefer settling in and spending real, quality time with you.

4. He's Acquired More Knowledge

His age and worldliness generally make him more interesting than guys your age. He's lived more, seen more, and understands people and the world differently. That means he can introduce you to experiences you've never had (30 awesome date ideas) and expand how you think about things. Sexually, his experience often means he can teach you a thing or two, like how to have better orgasms and more satisfying sex positions.

Of course, you can return the favor with an unforgettable blow job and the right techniques to fully satisfy him.

5. He Has Money

The classic (if a bit tired) reason younger women date older men is financial, and sure, that can be a genuine perk — though it comes with baggage too. She often gets labeled a gold digger. But dating a wealthier older man doesn't automatically mean money's the whole story. As long as both people are fine with the arrangement, it's really nobody else's business.

If money is part of your reasoning for dating older, expect some judgment from outsiders — but don't let that stop you if you and your partner are both comfortable with it.

Here are some of the problems with dating an older man:

1. His Friends and Family Don't Take You Seriously

Don't count on his circle celebrating the relationship. They probably won't be congratulating him on landing you. More likely, they'll assume you're after his money and predict you'll bail the moment you get bored or find someone else.

Even if he's not wealthy, his friends and family might still write you off as having little to offer because of your age, treating you with a bit of condescension.

2. Your Friends and Family Wonder Why He's Dating Younger

Your own circle probably won't be thrilled either. Expect the raised eyebrows and questions about how you two even met — they'll likely feel protective. They may wonder if he's only after sex, and worry that once you're no longer "young" in his eyes, he'll trade you in for someone newer.

Unfortunately, not everyone understands how men fall in love — there's no single explanation, just many possible ones.

But maybe you're not looking to settle down right now, or a casual dynamic suits you fine.

3. You Might Not Be Aware of the Same Pop Culture

A lot of his references will fly over your head when dating older, and vice versa — your current pop culture mentions might get you a blank stare. You just won't connect on that front the way you would with someone your own age. It's rarely a dealbreaker, but it's a small reminder of the age gap between you. It might not bother you much, but it's undeniably there.

Even if you're both happy to explain your respective references, spending lots of time with each other's friend groups probably won't feel natural for either of you. You might feel like you're out with your parents, and he might feel like he's tagging along with his kids' friends.

This can even show up in the ways you express love to one another.

4. Baggage from Prior Relationship

Dating older usually means he's already had at least one significant relationship — maybe even a marriage — before you came along. He might have kids from that relationship he supports and sees regularly. You won't be the only priority in his life, and his past relationship may still take up emotional space. If a previous breakup was especially painful, he might not be fully over it — possibly ever — which could leave him hesitant to remarry or fully open up again.

Learn: How to have great sex after marriage

5. You Want Kids, But He's Done

If he already has kids — possibly grown ones — from before, he may have zero interest in starting over with a new family. And if his kids are grown, they're likely close to your age, which can get awkward. Even without existing kids, at his stage of life, he might simply be done wanting them. If having your own children is a goal for you, this relationship probably isn't the right fit. Shared life goals matter for both the relationship overall and sexual compatibility.

6. Health Issues

You might want to hold off on snooping through his medicine cabinet when dating older. If he's not too far along in years, health issues might not have shown up yet — but they likely will eventually. The older he gets, the more likely health problems become. Men also tend to develop heart disease earlier than women and may face prostate issues down the line.

Side Note: Prostate massage can help with this and feels great too.

If you're still young yourself, thinking about your partner's future health issues probably isn't on your radar yet.

Dating an older man comes with its share of challenges, but they're workable if you're genuinely committed to the relationship. After all, dating younger has its own set of complications too.

As long as you're aligned on values and relationship goals, don't let the age gap stand between you and what could be a great relationship with an older partner.

February 17, 2022