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, 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:

Before I answer your question I want you to be aware that you are really overthinking this.

Bill asked you to dinner.


I doubt he is going to surprise you with an engagement ring on your first date.

If you are analyzing every man who asks you on a date by assessing whether they are husband/long-term partner material, you are going to miss out on a lot of fun, including wild couplings with highly inappropriate partners you’d go to bed with but never introduce to your Judge Judy of a mom.

Speaking of your mom, you told me when we texted this morning that she is 60 and single. Perhaps her advice to you was based upon anger that you are dipping your young and shapely bucket in her elderly suitor well.

Before I opine on the age difference I’ll point out the more pressing danger presented here 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 off the pier where you Zumba, or something like that.

This is 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).  Then again, Bill is so old he may have a tough time seeing you at all or catching up with you if you scamper into another room to avoid him.

Should Christine Date an Older Man?

My answer is unequivocal and resounding:


Christine, if you find Bill attractive and interesting enough to spend time with, do!  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 focused upon the age difference you should 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 fun. 

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 (my bad habits notwithstanding) I will be a widow someday.  

Being alone doesn’t frighten me, but being without him does.

That fear bubbles to the surface on the rare occasion when I consider our respective ages but the harsh truth of life is we risk loss every time we fall in love. People are taken from us randomly and without reason, regardless of age, so it’s best not to think about it too much.  

I find ignoring or denying the inevitable (such as death and my credit card bills) makes me a happier person.  You should try it!

Socially Speaking

Socially, being with someone older can be interesting. I now spend a good deal of time with people almost 20 years older than me.

I belong to a golf club (thanks to my husband because they would have never let me in otherwise) and I think the average member age is about 65.  The tampons in the women’s bathrooms are there nostalgically; not for practical purposes.

(In case you are wondering, I’m not worried his friends will see this blog.  Most of them don’t know about the Internet and those who do think MySpace is the bomb.)

However, these older friends have been supportive and caring since meeting me and I do not always feel like the “younger woman.” As it turns out, 60+ year-old men and women can be as obnoxious and immature as I am!

Mr. Patience and Understanding has also become close with my friends, who seem to like him more than me.  Go figure.

What About Bill?

You aren’t the only one facing the age difference challenge if Bill starts putting on your very green green.

Consider how he might feel about dating a woman 20 years younger than he is and one with young children to boot.  You told me his kids are grown so he may be facing trepidation of his own.  Not many people are keen on going back and doing the young family thing all over again.

Advice (finally!):

Christine, don’t over-think this.  Relax.

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 3 Comments

  1. Scott C.

    You are right on as always. Thank you Robin.

  2. Laurie

    Age is only a number. Don’t let it get in the way. My husband is 28.5 years older than I am. I’m 45. He’s 73. I was 25, and he was 53 when we started dating. We were together for almost 7 years before we got married. Everyone had their opinion about our age difference, but I held true to what I was feeling and didn’t let anyone else’s opinions influence me and my decisions. Go out with him, have fun, and just enjoy and live in the moment.

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