8 Things That Come Up When You’re Dating an Older Man

A woman dating an older man, kissing him on a dock in front of a beautiful mountain.

There are plenty of perks to dating older men. Usually, they’re a little more advanced in what they’re looking for, meaning they aren’t expecting you to spend three hours curling your hair before the big date. They’d rather use that extra time to grab a drink before your movie, where—honestly—nobody will see your hair anyway. Older guys are also a little more mature, meaning that they’ll be more upfront about what they want out of a relationship, and tend to go for what they want without a lot of games.

But, if there’s an age-gap between you and the guy you’re dating, there are a few things about older men that you should know prior to making things official. Here are some things to consider before taking that next step.

He knows what he wants.
If you’re looking for a serious relationship, but he’s going for something casual, there’s a good chance you won’t be able to change his mind—regardless of how compatible the two of you are.

Older men have a good idea of what they want and how much emotional energy they have to put into a relationship. It’s important for the two of you to be on the same page about expectations. If he’s not looking to get married, you need to respect that and not force the issue a year or two in.

He probably has more romantic history than you.
If he’s older and single, there are three possibilities at hand. He could be a widow or divorced, he could be a serial dater, or he’s simply been single and happy with it for plenty of years. But chances are, it’s one of the first two. If you’re the type who compares themselves to someone’s exes or if you can’t handle a significant relationship that was part of your man’s life, this arrangement might not be the best fit for you. Everyone has a past, but some of us have a lot more past than others. You’re either ok with that, or you’re not.

Kids may be a bigger issue.
There’s a chance he might have one or two kids from a previous relationship, meaning that if things got serious, you may very well be a step-parent. It’s a high honor, but a little tough if you aren’t fond of children or aren’t ready for that kind of responsibility. He might have also have aged out of being interested in having kids. That means that if it was always part of your life plan, you may have a tough decision ahead.

You need to think ten years head.
Listen—the scariest part about life is that it’s completely unpredictable. As humans, we have to make the best choices we can. But when you’re dating an older man, there’s a good possibility that if the two of you get serious, you’ll be more active in managing his health than your friends would be within their own relationships. Men don’t suddenly fall apart after a certain set time, and everyone’s different—but it’s still something you need to be prepped for. Are you emotionally able to be his support at a younger age? Are you going to be ok, if he ages faster than you and isn’t interested in the same things you are anymore, or isn’t able to travel or be as mobile when you get older? These things seem far away, but they’re important enough to start thinking about now.

He’s likely to be set in his ways.
Many older men are looking for a companion, and not necessarily someone who’ll ask them to make a bunch of changes. If he’s been living by himself in an apartment, it may be tough to get him to agree to move in together. Especially if things have been just fine in the visiting arrangement you’ve already set.

There might be moments where he makes you feel immature.
With age comes wisdom, but that doesn’t mean that you should always feel like you’re in the wrong. While dating an older man has a lot of perks, be prepared for the moments where he tries to show you up, or make you feel as if your opinion is misguided. It’s a character flaw that many older men have, and older people in general for that matter. Simply put, they think they’re in charge because they were born earlier than you were. Just note that if this is a constant pattern, you should call him out on it or cut your losses now. Constantly feeling bad isn’t a necessary part of any relationship.

Friends and family might have opinions.
If there’s a significant age gap, you’ll get some questions throughout the entirety of your relationship. People might make jokes, or wonder how the two of you ended up falling for each other. Even if the age gap isn’t that big, you might still feel some distance from close friends, especially if your guy is a little old for certain venues. If there aren’t any red flags (and a trusted loved one would let you know if there’s something you aren’t seeing) and the relationship is legal—since that’s an absolute must—remember that all relationships are different. If he treats you right, that’s what’s most important.

Your interests may differ.
As time goes on, you might realize that you actually don’t have as much in common with your older guy than you initially thought. That’s totally natural, and not necessarily a dealbreaker—at least, unless you think it is. There’s a good chance that you won’t be nostalgic about the same entertainment, and may not even understand each other’s preference in music. Just remember, dating someone with completely different tastes may be a great learning experience.

Like all relationships, dating an older man will have its challenges. If it’s your first time approaching someone older, be open minded and ready to adjust to new dynamics. It can certainly work and be an amazing relationship for you, but like anything worth pursuing, it’s not all going to be easy either.

Karen Belz

Freelance Writer

Karen Belz has written for sites like Bustle, PreviouslyTV, Heavy, and HelloGiggles. She’s also the founder of Best Recap Ever, a site that’s focused on television news and reviews. She’s a fan of sketch comedy shows and most movies that involve Muppets, and has been addicted to Sugar Free Red Bull since 2005.

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