Ask Dr. Gilda-I Want To Date My Son’s Friend

One woman is smitten with her son’s soon-to-be-divorced pal. Is it wrong for them to get closer?

By Dr. Gilda Carle, Ph.D.

ear Dr. Gilda,
I’m 46 and divorced for five years. I have been getting to know my son’s good friend better; he has been an acquaintance of mine for years. And he’s closer in age to me than he is to my son. We have only gone out twice, but we get along well and
I know he is still in shock and shouldn’t date for a while.
really laugh. We text-message and talk to each other on the phone. The problem is that he just separated from his wife of 24 years about three months ago; she left him. I know he is still in shock and shouldn’t date for a while.

My question is: At what point is it safe to take this beyond friendship? I do not want to ruin a potential relationship with him, but it is really hard to stay platonic. He has even said he doesn’t want me to be his rebound, but we really skirt around the issue. He is also pretty close to my son. Is it safe to see him once in a while and keep talking to him?
– Tired of Being a Friend

Dear Tired,
Your sign-off is “Tired of Being a Friend”—after only two dates! But a friend is exactly what this guy needs from you now. Your own hormones may be surging, but your timing is off. The guy is shell-shocked. He is just starting the divorce process, so his breakup is in its early stages. As you wisely admitted, “he still has a lot to go through.” Yet you clearly want to jump his bones. Slow down!

Rebounds are a normal consequence of breakups, and if you’re in this guy’s bed now, that’s what you are likely to become. Having “only gone out twice,” of course you “get along well and really laugh.” You’re both still on your best behavior. You say, “We text-message and talk to each other on the phone.” Lady, that’s because you are in the role of older, wiser woman who has been there and done that. You have a lot to share, and he feels safe with you. But you ask, “Is it safe to see him once in a while and keep talking to him?” Safe for whom? For him, you’re just what the doctor ordered. But for you, who have been single for
Hooking up with this guy is a sure way to heartbreak.
five years and undoubtedly lonely, it is not.

Hooking up with this guy is a sure way to heartbreak. He does not know who he is as a single entity, he does not yet understand what just happened to him, he’s still sorting what went wrong in his marriage, and he’s hurting so much, he’ll be unable to give any emotional support to you. If you want a one-sided, I’ll-show-you-the-ropes romp in bed, that’s exactly what you’ll get—but nothing more. And that uneven distribution of power will upset you in time.

This is what I suggest you do:
  1. Accept this guy as a poor love mate for now. Continue the friendship if you want to, but only that.
  2. Connect with other men who are emotionally available and who can return the loving emotions you dispense to them.
  3. Examine why you would choose someone off-limits. Is it because you want to have a controlling role in a romance? Is it because you really don’t want too much closeness? Does it have something to do with your relationship with your son—trying to become closer to him or to show him your youthfulness? Understand your motives.
This guy can’t give you what you think you want. As my Gilda-Gram says, “Become boyless before you become joyless.” Find the right person at the right time, or find out why you don’t. Being friends with him may seem to be an option, but I think you are kidding yourself. I don’t think you two would be able to have just a friendship right now, given your feelings. My advice to you then is to put this connection on ice until enough time has passed for him to heal. By then, who knows where each of you will be and what each of you will want?

Relationship expert Dr. Gilda Carle, Ph.D., gives Instant Advice throughout the world via Skype, email and phone. She is the 30-Second Therapist for Her best-selling books include Don’t Bet on the Prince!, 99 Prescriptions for Fidelity and How to Win When Your Mate Cheats. Please visit her website at (
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