How To Date A Younger Man

Senior Dating

How to Date a Younger Man

Nick Slade

Written by: Nick Slade

Nick Slade

Nick spent 20 years in the dating scene before marriage. He has always been the guy friends would come to for advice on relationships, and he developed a knack for giving helpful insights. After college, Nick was a disc jockey for a few years, when the love generation was still alive, so Nick has a lot of relevant experience to draw from when it comes to every aspect of dating, falling in love and screwing things up. He holds Bachelor's degree in humanities and a slew of master’s credits in journalism. Nick is a news junkie and tries to keep up on the latest non-fiction when he has time. He has published two books on how to win at dating and relationships.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Mark Twain famously said, “Too bad youth is wasted on the young.” But today’s older women are discovering what older men have know centuries: Life’s a little better when the young waste some of their youth on you.

It makes you feel younger, more vital and more involved in life and the world again.

There’s no need to take things to the “Harold and Maude” extreme to enjoy the benefits of dating a younger man, but a gratuitous fling with a younger guy did help Stella get her groove back.

It can be a rewarding experience, but before you jump into the youth pool head first, it’s best to know what you’re getting into and have some kind of plan to make it all work.

Examine your motives.

There are a lot of great reasons for dating younger men, some of which we’ve just mentioned. But why do you want to do it? And how young is too young?

The answer to the second question depends on your answer to the first. Are you looking for fun, or are you looking for a meaningful and lasting romance?

If you want to play the cougar game, then be prepared for plenty of passion, but check your emotions at the door before you leave home. Go ahead and live out some of those fantasies you were too shy or inhibited to try when you were younger.

Teach some young guys how to be real men or just enjoy their youthful exuberance. But stay away from the schoolyards, and don’t play with anyone’s fragile emotions.

It’s more likely, however, that you just want to turn the clock back a decade or so and recapture the years that just slipped away in a bad marriage, a career-absorbed spinsterhood or a post-divorce black hole.

Guys don’t even consider a 10-year difference to be a big age gap, as they almost always date somewhat younger. But women typically date guys a little older, and this magnifies the spread.

You still feel young and vibrant, and maybe you feel like you got cheated out of some of the best years of your life by bad circumstances or frozen emotions. Or perhaps you know somebody who has recently become available because of a divorce, or maybe the older guys just don’t interest you anymore and can’t fulfill your needs.

In any case, you now sense a certain urgency and compulsion to pursue a life with a younger man.


“If you find yourself forgetting you’re

older, then that tiger can be groomed.”

Consider his motives.

Younger men have always been attracted to older women, and they always will be. From those early crushes on the babysitter or elementary school teacher, guys have found fascination and comfort in the loving eyes of attractive ladies many years older.

It is not only possible but likely that his feelings are true and well-intended. After all, you’ve still got it.

Nevertheless, you need to get a sense of what he’s after. He might like the status and security of being with an established partner who has accomplished great things and is financially independent.

Perhaps it would give him the ability to pursue his artistic or entrepreneurial endeavors that might not pay off for some time. If you love each other, that’s not a bad thing. Just don’t be his major investor.

He might find the maturity and stability in you that younger women are lacking. And he might find the compassion and understanding that will allow him to develop as a lover, whereas the younger women have no patience for a man who is lacking in romantic experience.

He might appreciate the lifestyle you can offer him. He can still work hard to get ahead in his career, but you can provide fun weekend experiences and great vacations along the way.

Women have been doing it with older guys for years. It just depends on how that sits with you.

He might have growing or grown children with his ex-wife and has no desire to be with a woman who still has children at home. He might find you sexually irresistible, or he might just be head over heels in love with you.

It is up to you to decide what motivations on his side of the equation are acceptable to you and which are not. And you also must keep your mind alert to the possibility that he just wants to use you for some devious purpose.

Remember who you are.

Don’t fall into the trap of trying to be younger than you really are. Don’t dress like a hip hop party girl or go clubbing, drinking and smoking until the sun comes up. And don’t try to go rock climbing with him just so he won’t think you’re too old.

You can love him for what he brings to your life, and you should let him love you for who you really are and for what you add to his life.

Dating a younger man is a valid choice for any woman, and it’s really nobody’s business but your own.

If your friends or kids have legitimate concerns, you should hear them out and heed their warnings to a rational degree, but his age alone is not a good enough criticism. It may or may not work out, but you’ll never know until you give it a try.

The real test will be how things feel to you after a few months of dating. If you continue to feel that you are dating a younger guy instead of just dating a guy, then you might want to consider why that is.

If the lifestyles don’t sync up very well, if he’s always gone or too active, or if his goals or maturity level just don’t seem to mesh well with yours, it might be time to end the experiment.

But if, instead of constantly thinking of him as younger, you often find yourself forgetting that you’re older, then maybe that tiger you grabbed by the tail can be domesticated and groomed into a great partner.

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