Dare to Ask: He dated daughter, now wants mom

By Phillip Milano

Question

I’m 36 and just broke up with a 20-year-old, Michele, who was too young for me. Though we were intimate, we are parting amicably. Her mother, Linda, is 37, divorced and as sweet as her daughter. I know Linda is very attracted to me, and though I think we’d make a great couple, we haven’t said anything to Michele (Michele and I would have split, anyway). Is it wrong for me to pursue Linda?

Doug, Jacksonville

Replies

[It’s OK] only if Michele is OK with it.

Cathy, 49, Clarksdale, Miss.

The fact that you and Michele were intimate makes this easy: Yes, it is wrong for you to pursue her mother. The relationship you had with Michele probably will rear its ugly head, and it’s not worth the pain, awkwardness or possible distrust.

Dorothy, Phoenix

If you have any respect for Michele, you should cool it with her mother. … It also sounds like Linda is as selfish as you seem to be.

Marsha, Mountain View, Ark.

If you’re serious about Linda and it got to the marriage stage, you would have had sex with your stepdaughter, which is a little disturbing.

Jemma, Adelaide, Australia

Have you ever heard the term [an unprintable, four-syllable compound noun beginning with the letter m]?

Gary, 47, Houston

Expert says

Diane Mapes, who writes about dating at singleshot seattle.wordpress.com, has heard lots of unusual things people want to try.

But this one “skeeves me out,” she said. “I think it would skeeve others out, too, like his friends, colleagues and family, and the mother’s and daughter’s friends, colleagues and family.”

The truth is, we all run into people we are attracted to and wouldn’t mind having a go with, whether co-workers, in-laws, cousins or even our minister, she said.

That doesn’t mean we actually have that go.

“Do you want to put up with the drama and turmoil that having sex will bring?” said Mapes, author of “How to Date in a Post-Dating World.” “I suggest this guy move on and not try to nail every member of this particular family.”

The problem is the possible major damage to the mother-daughter relationship, in terms of doubt and mistrust, Mapes said. There might always be comparisons being made, too, and questions of whether Michele’s former boyfriend is still attracted to her.

“These things happen in the movies, but movies last for two hours, and then everyone goes home,” Mapes said. “In real life it can cause pain and anguish. Sure, it can be two hours of fun in there — or 22 — but I don’t think it’s a smart idea.”