I am a 46-year-old, young-at-heart, beautiful, sexy woman. I was married for 22 years and divorced 5 years ago. I love being married but realized I wasn’t with a man that made me happy. I have 2 beautiful kids, a son who is 24 and a daughter who is 21. I thought I would be happily married by now! I keep wondering what I am doing wrong. I’ve read your books, e-mails…

A year ago I met a man who is 13 yrs younger, with no job, new from NY, no money but was very persistent in becoming friends. At the time I was starting my new business and needed a roommate, so he was perfect! So I thought!

It quickly became romantic and he fell deeply in love with me and worshiped the ground I walked on. I, on the other hand, had feelings for him but nothing like that. Selfishly, I don’t want to be alone. I asked him to move out a month ago so I can get my feelings straight. I miss his companionship so severely that I catch myself crying. I know he’s not my future husband but I feel safe with him in all areas. Evan can you PLEASE help me? Thank You. —Shelly

Everybody listen up.

If you flip the genders and re-title this “Is It Wrong to Use a Younger Woman for Companionship”, this could be an email from a lonely man in his mid-40’s, post-divorce.

Objective reality is messy and grey and fraught with danger.

I am confident that if a man wrote the above email, most women would find it abhorrent that he would think of having his younger girlfriend invest her time in him, even though he knew that they were doomed in the long-run. And yet I would think that most readers are somewhat sympathetic to Shelly and can imagine how they’d feel in her situation.

Ready for Lasting Love?
Ready for Lasting Love?

This is why it’s dangerous to tar men as “players” or “users” or “liars” when they’re dating you without long-term intentions. Sometimes, even the nicest people, like Shelly, do something selfish that will have a negative impact on a romantic partner.

While it sounds nice that everyone should state his/her intentions at the beginning to avoid wasting anybody’s time, that’s far easier said than done, folks.

Which is to say that I’m not a moralist. I’m a pragmatist.

And whether I’m telling women that men look for sex and find love, so don’t sleep with him unless you can handle the consequences, or telling men that they’d better pay for the first date or they won’t get a second date, I try very hard to deal in objective reality.

Objective reality is messy and grey and fraught with danger.

What’s right for you is not necessarily what’s right for him.

What’s right for him is not necessarily what’s right for you.

All relationships are about navigating that space between those two realms with a measure of integrity.

So, Shelly, I don’t know how long you were together. A week? A month? Three months? One year? But you claim that he was “deeply in love” with you when you broke up. Fair enough.

If that’s the case, you did the right thing by kicking him out.

What’s right for you is not necessarily what’s right for him.

What’s right for him is not necessarily what’s right for you.

You sacrificed some measure of short-term personal pleasure in order to avoid creating a world of hurt for your younger boyfriend.


This was the most ethical thing you could do — and is very consistent with the kind of thing that I routinely did when I was single. (That’s why I never had a girlfriend for longer than 8 months; the second I knew that I wasn’t going to marry her was the second I got out.)

However, I don’t want you to beat yourself up over the fact that you are lonely and still have feelings for this young man.

Pretty much EVERYONE who EVER breaks up with a romantic partner — presuming the relationship wasn’t disastrous — suffers considerable regrets in ensuing weeks and months. Factor in that you were living together, and, well, it’s almost as if you suffered another mini-divorce.

So what are you to do, given that you’re both sad and lonely and miss each other?

I would say that you should stick to your guns and cut him out of your life entirely. No contact, no hope, no texts, no nothing. Only then can you both ably move on from your unrealistic entanglements.

Yet if you were to reinitiate contact with him, you would have to do so with the knowledge that it’s a long-term mistake for both of you — that the pleasure you’ll gain from sex and companionship is going to ultimately pale compared to the pain you’ll experience when one of you eventually pulls away from the other.

In other words, you can call him up and “use” him again to fulfill your temporary emptiness. Men and women do this every day by staying in flawed romantic partnerships, presuming it beats being alone.

Just don’t kid yourself about the consequences.

You’re going to temporarily soothe your own discomfort, but you’re going to destroy this guy who thinks he has another chance with you.

I don’t judge you either way, but that doesn’t mean that there isn’t an ethical path out of your situation.