When it comes to dating, age is just one among many factors to consider as you seek your match. We bring all of our prior life experience to any relationship we enter, so how much does it matter that one person's history is years (or decades) longer than the other's? Here, two experts weigh in on the benefits of dating an older man, as well as the potential drawbacks.

Dating an older man in your 20s and 30s is much different than dating one in your 40s, 50s, and 60s.

While an older man dating a younger woman tends to raise less eyebrows than a woman's romance with a younger man, the dynamic isn't exactly stigma-free—particularly when the age gap is significant. When a young woman named Courtney Thornton (née Barber) took flak both online and off in 2016 for falling in love with a man 25 years her senior, she started the hashtag #husbandnotdad to encourage others in the same boat to share their stories. Three years later, search #husbandnotdad on Instagram and you'll find a collection of smiling couples; on Twitter, the same hashtag's happy photos are interspersed with searingly critical comments, which arguably confirms Thornton's point.

When women over 40 find themselves drawn to someone who's older, they are less of a target for those who cry 'daddy issues.' "In your fifties or sixties, most women are independent and financially stable," says Charly Lester, co-founder and CMO of Lumen, a dating app for people over 50. "They're less likely to experience the same judgments and stereotypes if they decide to date an older man at this age."

A range of generation gap-related issues (more on those below) can be easier to bridge when you're over 40 as well. "The older you get, the less of a challenge it's likely to pose," Lester continues. "In terms of life experience and maturity, an age gap at 50 or 60 isn't particularly dramatic."

An older man who's worthy of your time knows what he wants in a relationship.

Stability, a strong sense of self, and advancement in his career are things older men can potentially bring to the table more often than a man in his 20s or 30s can, says Sherman. "People often ask whether an older man is more mature than a younger one," Sherman adds. "It depends upon the individual and their development and history. That said, extra years of life experience do often lead to greater maturity in relationships, and more life wisdom."

A woman in her 40s or older has plenty of hard-won lessons and accomplishments of her own to tout, of course. She just might love getting involved with a person who's on equally-solid ground (and has been there for awhile).

With kids out of the nest, an older man may have more time for you.

Maybe you're dating after a divorce, and you're a single mom who needs to carve out the time for a love life. A man who's already been married and raised kids has no carpool schedules to contend with, which can mean he's got more time to plan amazing dates. According to Lester, if you're seeing someone who is ten or more years older than you, "he's likely to have children who are less dependent on him, and have more free time—which can be particularly helpful if your kids are still more dependent."

If he's retired and you're not, relating to each other can be a challenge.

If his working days are behind him and you're still focused on a job and all the ambitions, woes, and time demands that come with it, you may struggle to connect at the end of the day. "Often relationships are built on similar life experience, and the difference between daily work and retirement can be quite a marked one," Lester explains.

Find out whether your visions for the future match up.

You two may not be picking out wedding rings at this point, but if things start getting serious, it's worth discussing what you both think your next ten-to-twenty years will look like. Do you have any further family ambitions? Are you open to traveling, or moving somewhere else?

"Make sure that you’ve discussed important issues like whether you both want kids, and whether you can mutually support one another’s dreams and the things that make you both happy," Sherman advises. "One person may feel like their goals are winding down and the other is winding up."

You may discover some surprising cultural differences.

So he doesn't know who Cardi B is, and you don't have the same points of nostalgia—that might not bug you at all, and that's just great. But what if you start talking politics and trends, only to discover he's completely immovable in his views? It certainly depends on the individual, but "he may be very set in his ways and can appear less open-minded than younger men," Paulette warns.

Lester agrees. "Someone who grew up twenty years before you may have different cultural references, or a less liberal approach to certain political or social topics, which can cause friction in the early days when they meet your friends and family," she says.

Your communication habits may be different.

Or, you know, they might not be. While Sherman says an older man may prefer you to call him rather than sending a string of texts, Lester says that's not necessarily true. "In my experience with running a dating app, there are surprisingly less differences between the way a 30 year old, a 50 year old, and a 70 year old communicate. We have people in their 90s using it!"

Remember that it's about the two of you as individuals, not your age difference.

Your difference in years may elicit some unfortunate assumptions and remarks, but if you truly care about each other, stay focused on how you feel. "Try remembering the things that you love about the person as an individual," says Paulette Sherman, a psychotherapist and certified dating coach. "It’s important to recall why you chose your partner, and not to let outside stigma or judgments dissuade you."


For more stories like this, sign up for our newsletter.

Headshot of Samantha Vincenty
Samantha Vincenty
Senior Staff Writer

Samantha Vincenty is the former senior staff writer at Oprah Daily.