Susan
March 6, 2025
Some women just can’t resist the allure of a silver fox who’s built up a solid 401K. Sound like you? Catherine Zeta-Jones, Blake Lively, Kate Upton, Heidi Klum, Beyonce, and Amal Clooney — these are just a small handful of the many beautiful women who have married or dated men 10+ years older. So, needless to say, you’re in good company. But before you get all wrapped up in one of these relationships, you’ll want to know my top tips for dating an older man first. Because the reality is, this type of dynamic requires some special considerations.
A lot of people ask me: is dating an older man a good idea? The short answer is: It can be. Let’s talk pros and cons. Odds are, at this point in his life, he knows who he is, he knows what he wants, and ready to commit because he’s so over playing games (been there, done that). Not only that, but he’s figured out how to dress, he can read a wine menu like a pro, and he can afford to whisk you away on a romantic weekend getaway. What could be hotter than that? An older man may have a certain calmness, confidence, and poise about him that only comes with age. He might also have more financial stability to offer, and be more established and successful in his career, than a younger man. But there are potential pitfalls as well. Namely, when you date older, you risk potentially having less in common. Specifically, you may have conflicting goals and priorities, or have different ideas of what you want in the future.
That’s not to say you should never go older. In fact, a 2016 study of relationships conducted at St. Mary’s University (Halifax) found that age gaps, no matter the size, do not have any bearing on someone’s satisfaction with their partner. However, there are some important things to keep in mind. If you want your connection to survive — and thrive — here’s my advice for dating an older man.
Be aware that you might not always “get” each other.
If you grew up in different decades, you may not have watched the same shows, listened to the same bands, or experienced world events in the same way. So, at times, your pop culture references might go right over his head. When that happens, you may start to feel like you’re from different planets. But who knows? At the same time, maybe you’ll learn to find it kind of adorable that he doesn’t know who TF Halsey is. As long as you tolerate each other’s taste in music, movies, etc., it’s fine if you’re not into all the same things (that’s boring anyway, IMO).
Accept that people may judge you.
Your friends might raise their eyebrows or make jokes, his friends might call you a gold digger behind your back and your family might just be freaked out by the whole thing. You’re going to have to get over that if this is going to work. There’s a bit of a stigma around dating someone much older (or younger) — although arguably, less so for women dating older men than vice versa. Age gaps tend to make people uncomfortable because they’re somewhat outside of the norm, but the important thing is that you feel good about the relationship. If you’re insecure, you may let those outside judgments get to you.
Consider whether you have different definitions of fun.
First off, you might want to prepare yourself for some awkward group gatherings with friends, because your social circle may not have much in common with his if there’s a significant age gap between them. That’s totally OK, but it’s something to be aware of. Also, if your ideal Friday night is hitting the local dive bar and dancing till 2 a.m., and your older beau would rather have a quiet, intimate dinner at a classy establishment, you may run into some issues. Maybe you can find a middle ground — sometimes you sleep in and have a lazy brunch, and sometimes you get up early to go for a run.
Embrace the fact that he had a whole other life before you — and resolve to build a new one together.
Maybe he was already married or even had kids. Or, he’s traveled all around the world, when you have yet to even leave the country. He could have already crossed off most of the things on your bucket list. You’ll need to come to accept all of this — and hopefully find new “firsts” to enjoy together, like making your own wine, taking a road trip to a state neither of you has been to, or trying out something super creative in the bedroom. And remember — the good news is that because he has a few years of experience on you, he’s likely gathered some wisdom about matters of the heart — and you’ll benefit from that.
Talk about your communication habits and expectations.
If you’re an avid texter, Instagrammer, and tweeter, you may need to keep in mind that your older guy just isn’t as savvy about social media and other technologies. He may prefer to communicate the old-fashioned way. Sure, there are plenty of exceptions to this. But still, it’s a good idea to hash out your expectations when it comes to communication, especially if you’re used to having a boyfriend who sends you a string of emoji-filled texts throughout the day and that’s just not his style.
Evaluate whether you’re currently on the same page.
If you’re grinding away and working late nights to climb the corporate ladder and he’s already retired, it’s time to take an honest look at whether or not you’re in very different places in your lives. While some couples can make that work, the reality is that it might become challenging when he expects you to drop everything and jet off on an impromptu trip, and you’re still hustling at the office to try and get that raise. Will you be able to relate to each other in your day-to-day convos? That’s something you’ll need to ask yourself.
Talk about the future before getting in too deep.
If your biological clock is ticking away and you really want a family — but he already has one from a previous marriage, would he be open to having more kids? If not, that’s something you’ll want to think about. Whatever you do, don’t naively assume he’ll just change his mind down the road. Alternatively, if he’s super eager to have children while he still can and you’re far from ready to be a mom, that could also cause some tension. That’s why it’s important to have some conversations about the future ASAP once things start getting serious.
Look — as they say, age is but a number. And to an extent, that’s true. Why should you give up on a guy who could very well be “The One” just because he’s got a decade (or more) of life on you? Sure, dating an older man will come with some challenges — but then again, so do all relationships. If you’re ready to meet an amazing older man, I’ve got plenty of clients who are eager to spark up a connection. And now, you’ve got all the tools you need to build a happy, healthy bond with one.