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Into older men? Do’s and don’ts for dating an older man

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Hollywood is notorious for pairing its leading ladies with much older men — Julia Roberts and Richard Gere (18 years) in “Pretty Woman” and “Runaway Bride,” Helen Hunt and Jack Nicholson (26 years) in “As Good As It Gets,” Catherine Zeta-Jones and Sean Connery (29 years) in “Entrapment.” 

And of course, lots of male celebrities are known for dating younger women — Leonardo DiCaprio, George Clooney, Hugh Hefner, Johnny Depp, Michael Douglas, to name a few. Someone on Reddit even created a graphic showing that Leonardo DiCaprio has never dated someone over the age of 25: 

A May–December relationship — May representing spring/youth and December representing winter/old age — certainly isn’t for everyone, but research by dating app Badoo found that: 

  • 26% of 18-24 year olds would date someone older than 35
  • Nearly a third of women have dated someone 10 years older

If you believe age is only a number when it comes to love (or even an asset?), we recommend joining eharmony, our #1 choice for finding serious relationships online. eharmony is accredited with an A- rating from the Better Business Bureau and allows its members to filter matches by a number of specific criteria — including age.

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Keep reading to learn everything you need to know about dating older men:

Why you're into older men

Being attracted to older men might be ingrained in our psyche, says Sarah Hill, evolutionary psychologist and author of the book This is Your Brain on Birth Control. She says our preference for older men has deep evolutionary roots. 

“Dating older men promoted the survival and reproductive success of our female ancestors and their children,” Hill says. This is because older men more often have the financial resources and intellectual maturity to provide for children.

Some researchers also believe younger women are into older men because of the belief that women mature emotionally more quickly than men, and therefore might seek an older partner to find a more compatible match. According to research published in the journal Cerebral Cortex, the female brain establishes connections earlier in life than the male brain. 

What to expect when dating older men

Dating an older man can hit differently than dating someone your age — or younger, says Nancy Keisling, Adventure Dating Coach with Scott & Nancy Consulting, a life coaching business she runs with her husband Scott, who is 10 years her senior. 

In Keisling’s experience, older men tend to be more thoughtful and serious about commitment. 

“They understand boundaries better and support your desire for individuality and independence instead of feeling threatened by it,” Keisling says. “They can see a perception bigger than their own, which makes you feel seen and heard.”

For Eva Keller, 27, dating an older man meant low-key dates, a welcome change from rowdy 20-something guys who preferred to go out.

“I think on a more subconscious level, that part of the attraction was that I'm an introvert and live a more homebody type of life than most others my age,” says Keller, who is married to a 52-year-old man. “I think my nervous system had just found its match and found someone I could align myself with within my own comfort zone.”

Pros and cons of May-December relationships

These are some of the pros and cons of dating an older man:

Pros of May-December relationships

They're financially stable

Older men are generally more established in their careers, Hill says, which typically means they can have a good chunk of savings and financial security.  

When Keller met her now-husband, she was an intern, and he was able to help support her when they dated. 

“I didn't really have the money to go out to eat like I grew up doing, but by hanging out with my future husband every day, he was providing that lifestyle that I was used to and expected to have.”

They've been around the block

Chances are you're not this man's first serious partner, and he’s hopefully figured out most of the dos and don’ts of dating.

“Personally, the best part about our age gap is that my husband is mature,” Keller says. “He doesn't start petty fights, he doesn't play games, he's too tired to cheat, and he doesn't go out and get drunk every chance he gets. Other women my age are stuck with these ridiculously immature guys that I could just never imagine being in a situation like that.”

Cons of May-December relationships

Being older means a higher risk of health issues.

If women choose an older male partner, there is some risk she will be alone in later life, Hill says. Currently, the average life expectancy for men is 75.1 years, compared to 80.5 years for women, according to the CDC

Other things to consider? Older men may have a decrease in sexual stamina (although, according to Hill, research says older men who are in good health have a lower rate of decline). A national study by the Cleveland Clinic that surveyed 1,410 men found that men between the ages of 50 and 50 were more likely to experience erectile dysfunction, and it was more likely found in men with poor and physical health.

Lastly, while older men are usually in a better financial place to have children, whether they can actually reproduce is another story; sperm count declines as men age, so choosing an older man as your partner could affect your chances of having biological children together, if that’s something you want to do.

You might have to deal with their past

“All of us have past experiences; he will have a little bit more because he's got more years than you,” Keisling says. 

For example, he might be dealing with a messy divorce or have kids to co-parent with his ex. Plus, the longer you are on this Earth, the more baggage and heartbreak you accumulate. Of course, this isn't bad per se, but something to consider when you're dating someone much older.

Dos and don'ts for dating older men

Do: Choose the right dating website

Quality older men probably aren't using modern dating and hookup apps like Tinder. Consider a dating website or app like eharmony, which has been around since the year 2000 and has a proven track record of creating successful marriages and lower divorce rates. eharmony uses an extensive compatibility quiz to help you find your perfect match.

Researchers at the University of Chicago and Harvard conducted a study of marriages, breakups and divorces by dating site where the couple met, and found that couples who met on eharmony had the highest marriage rate, highest marriage satisfaction rate, and the lowest breakup and divorce rates.

You can try eharmony for free or use code WSM25 to get 25% off a membership now >>

Check out our eharmony review and our reviews of other top dating sites and apps:

Tinder reviewMatch.com review
Bumble reviewAdult Friend Finder review
Plenty of Fish reviewCoffee Meets Bagel review
Zoosk reviewElite Singles review
It's Just Lunch reviewChristian Mingle review
SingleParentMeet reviewTawkify review
OKCupid review

Don't: Make the age difference such a big deal

Yes, there will be times in your relationship when you'll remember the age difference (like when you’re recounting a story from your Girl Scout days and realize he graduated from law school the same year). 

Keisling suggests not focusing on your age gap but rather the person you’re with.

“Men who date younger women usually feel young at heart and want to stay focused on feeling young,” she says.

Do: Be honest about your needs

Before starting a relationship with an older man, it's a good idea to reflect on what you want out of the relationship, Hill says. 

For example, if he has kids, are you comfortable being in their lives (recognizing those “kids” might be close to your age or perhaps even older than you)? Are you OK with the idea that he may not want to have more kids? If your partner gets sick, are you prepared to be a caregiver? 

“As long as women carefully consider the risks and benefits of these relationships – and communicate with their partners about any concerns they have – these can be incredibly successful unions,” Hill adds.

Don't get intimidated.

Remember: relationships should be an equal partnership. 

“Just because he is older and has more life experience doesn't mean he is superior,” Keisling says. “Your opinions still matter and hold weight.” 

Likewise, you both have equal responsibility for managing your careers, finances and emotions.

Do embrace your differences.

Hill says that generation gaps between partners can limit the number of things they have in common. Your tastes in music, movies, and overall life experiences can greatly vary. 

But Keisling says that’s not always a bad thing: “This is what creates polarity and keeps the conversation interesting in the relationship.”

Don't be jealous.

Confidence is a sexy trait in any relationship but is extra important when dating older men, Keisling says. 

“Older men are usually done with playing games and secure in who they are and where they are in life,” she says. 

She says if your partner has a good co-parenting relationship with his ex-wife, you need to be OK with her being in the picture.

Famous men who date younger women

Hollywood is full of older men who date younger women. These are some of the most famous: 

Leonardo DiCaprio

Leonardo DiCaprio's habit of dating younger women is almost as famous as his film career. It’s believed he’s never dated anyone under the age of 25 (check out the Reddit thread we mentioned earlier). He and his current girlfriend Camila Morrone have a 23-year age difference.

George Clooney

The once-famous bachelor dated multiple younger women until he settled down with Amal Clooney, who is 16 years his junior. The couple tied the knot in 2014, have two kids together, and are still going strong.

Famous May-December romances:

There have been plenty of good, bad, and just plain ugly May-December romances in Hollywood — we’ll spare you a rehashing of the Amber Heard and Johnny Depp trial. Here are some of the most famous: 

Katie Holmes and Tom Cruise

Once the Hollywood “it” couple of the 2000s, TomKat was a force to be reckoned with. Cruise, who is 16 years Holmes' senior, started dating the actress in 2004, and shortly after, he declared his love for her (who can forget that famous couch-jumping clip from the Oprah Winfrey show)?

Shortly after, the couple got engaged and welcomed their daughter Suri. They got married, only to divorce in 2012.

Florence Pugh and Zach Braff

Though they recently amicably broke up, 26-year-old Oscar nominee Pugh and “Scrubs” star Braff, 47, started a social media flirtation in 2018 and went public after working together on Braff’s short film, “In the Time It Takes to Get There.” 

Throughout their 4-year relationship, both stars received relentless commentary on their age gap, with Pugh repeatedly having to defend her relationship online. 

Catherine Zeta-Jones and Michael Douglas

Catherine Zeta-Jones and Michael Douglas (who have a 25-year age gap) first got together in 1998 and married in 2000. Although they briefly split in 2013, they got back together shortly after and have been together for 20+ years.

Bianca Mendez is a writer and editor living in New York City. Her work has appeared in Woman’s Health, Bustle, Latina, Refinery29, and many other publications. She also served as a sex and dating editor at Elite Daily and a freelance lifestyle editor for Bauer Publishing’s Teen Department, where she helped the team launch three new magazines.

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