Should I Date an Older Man?

Dear Robin:

I divorced about two years ago (I am 37 with two kids 9 and 11) and I hadn’t met anyone that really intrigued me until a month ago.  I met “Bill” at my gym and we started up a conversation one morning and since then, he seeks me out to chat every day.  These conversations are often the highlight of my day and I find myself thinking about him often.  He’s funny, very smart, handsome and thoughtful.

On Monday Bill asked me to dinner for this weekend and I immediately said yes.  Now I am wondering if that was a bad idea, and here’s why: he is 57 years old.  My mother thinks this is a terrible idea and I should cancel the date because this can never go anywhere, according to her.

I heard you on the radio in Palm Springs and you mentioned your husband is older than you.  I suppose that means I know how you will answer my question but I’ll ask it anyway because I want to share it with my mom: should I date an older man?  Is a 20 year age difference too much?


Dear Christine:

There are some May-December romances which work and make sense…


…and others which are just sort of gross and clearly motivated by money…


That being said, significant age differences aren’t for everyone, even when both parties have a genuine fondness for one another.  However, before I answer your question I just want you to be aware that you are really overthinking this.

Bill asked you to dinner.  Dinner.  I hardly think he is going to surprise you with an engagement ring on your first date.  If you are analyzing every man who asks you out by assessing whether they are husband/long-term partner material, you are going to miss out on a lot of fun.

Not only will you miss out on the wild sex with totally inappropriate partners you’d never bring home to your judge-y mother, but you’ll also lose the opportunity to date people so fucking lame that they give you awesome cocktail party stories for years to come.  So settle down, Christine, it’s the dating game, not the mating game.

As for your mom, you told me when we texted this morning that she is 60 and single. I think her advice to you may have been born out of anger that you are dipping your young shapely bucket in her elderly suitor well.


The other thing I’d like to point out before I opine on the age difference is the danger of dating someone at your gym.  If things go poorly, you may need to seek another place to exercise.  Don’t shit where you sweat, or fish where you Zumba, or something like that.

This is just something to keep in mind in case this budding relationship ends in tragedy, because avoiding people at the gym can be difficult (I should know) and you also have to face them at your worst: sweating, ruddy-faced and smelling disgusting. Then again, Bill is so old he may have a tough time seeing you at all, or catching up with you if you saunter into another room.

OK, as for whether or not you should date an older man, my answer is an unequivocal and resounding:

yes no maybe

If you find him attractive and interesting enough to spend time with, hell yes.  And that’s what you told me, so I’m leaning towards advising you to take a leap of faith with Bill.  Just make sure he has a knee brace and a helmet on, because old people are delicate and break easily.

However, if you are already so wrapped up in the age difference, you may want to ask yourself if you are suited for a romance with an older man.  I can tell you from personal experience that Mr. Patience and Understanding and I almost never feel our age difference, because I am wise far beyond my years and he has an immature streak that nobody knows about but me.

Oops.  Sorry, honey.


He is also in great shape and I am on a crusade to die relatively young, so we should both go in a blaze of glory in about 20 years – hopefully together and doing something naughty.  Get your mind out of the gutter; I meant robbing a bank.  Jeez, some people.

I bring up that point because the single most anxiety-causing issue for me that arises from being married to someone older is my fear of how I will handle losing him. Statistics suggest I will be a widow someday, and probably a fairly young one.

The thing is, what terrifies me about that is not that I’ll be alone, it’s that Mr. Patience and Understanding will be gone.  The fear of losing someone you love deeply is very different than the fear of being alone, and the truth is you risk that loss every time you fall in love.  People are taken from us randomly and without reason, regardless of age.

Socially, being with someone older can be interesting.  I spend a lot of time with people a good deal older than me, and that can be a challenge because sometimes I feel different from these folks.  I belong to a golf club now thanks to my husband, and I think the average member age is about 55 – 60. Seriously, the tampons in the bathrooms are there nostalgically, not for practical purposes.


But for the most part, these older friends have been supportive and caring since meeting me and I do not always feel like the “younger woman.”  I’m just a friend with slightly perkier boobs and peri-menopausal (a.k.a. “occasionally psychotic and prone to crying jags and night sweats), rather than long past The Change.

But Mr. Patience and Understanding has also become close with my friends, and we all get along just fine.  Honestly I don’t think any of us consider the chronological issue anymore.  And speaking of that, you have to remember that you aren’t the only one facing this challenge should you embark on a love experiment with Bill.  You might want to consider how he might feel about dating a woman 20 years younger than he is and one with young children to boot.


Christine, as I mentioned before, don’t over-think this.  Go on the date, have a good time, and buy your mother a vibrator and a subscription to Our Time, a dating site for older folks.  Please check in with me later and let me know how things are going.




This Post Has 7 Comments

  1. Debbie

    My parents were 18 years apart and had a great marriage. Because my father lived to 94, my mother did not deal with widowhood until she was 76. Her first husband, who was her own age, died in his 60s.

  2. YouCanLeadAHorticulture

    I am 25 years younger than my man, and I never regret being the age difference. It’s so true what Robin says about being worried about losing the person you love so much vs, being alone. To the letter writer: Go get your sexy cat daddy!

  3. jeff

    Robin, you’re in a May/July marriage, don’t you think? December is way too close to the end of the year. Besides, Mr. Patience and Understanding is the same age I am 😉 and I don’t want to be thinking about being a December guy just yet.

    1. askdescamp

      Jeff, good point. Let’s call it April/August? August is my favorite month of the year!

  4. Swifty

    Come on, you’re not the only trophy wife at the golf club.

    1. askdescamp

      Trophy wife? I think not. First of all, that would be one fucked-up contest if the winner got me. Second, I consider Mr. Patience and Understanding my Trophy Husband. So there! And we are the only couple I know at the club with a significant age difference, unless you count Mrs. Havercamp and her pool boy, Steve.

  5. Sandra

    I always liked older man! I do not know why, but I find them more intellectual and sexy. Robin, I loved your advise!!!!!

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