Ask Dr Gilda-I’m struggling to date in midlife

One single midlife mom worries that her age, teenaged son and desire to remarry are all driving potential suitors away online. Dr. Gilda explains how to overcome these so-called “challenges.”

By Dr. Gilda Carle, Ph.D.

ear Dr. Gilda,
I am a single mom in her 50s with a teenage son spending half the time with me, mostly summers and holidays. Reading men’s profiles, it seems I have more than one challenge to overcome; that is, my age, my status as a single mom, and the fact that I’m looking for someone to share my life with that’d
The next “challenge” you believe you’re up against is your age.
be okay with the fact that I can’t have more children. I have tried several dating services and met a few men, but there was no chemistry. I am attractive and look much younger than my age, I’m educated, professional, and independent with varied interests. I want someone who is like-minded and wants to settle down (and I say that in my profile — is that a turn-off?). Also, I have posted pictures of myself with my son at events — do you think these men are threatened by the idea of having to help parent a teenage boy? I’d rather use my profile to talk about myself and not my part-time custody arrangement in detail, but he is in my life and I’d rather that not be a surprise, either, since I’m looking to marry again. Any advice you can give me is much appreciated.
– Remarriage-Ready Rita

Dear Remarriage-Ready Rita,
If you believe that raising a teenage son part of the time is a “challenge,” that’s exactly the vibe you will transmit to your dates. No man with all of his faculties wants a woman with burdens attached. Adjust your negative mindset and project the picture of a life that you are managing and enjoying to potential suitors. Since you can’t fake the feeling of being in control, get the help of a therapist to plot your path to positivity.

The next “challenge” you believe you’re up against is your age. According to you, people 50 and older are all dried up, unappealing and unmatchable. So why don’t we just annihilate that sector of the population? And while we’re at it, we could also throw in extra points for knocking off single moms in that age category. Finally, the fact that you can’t have children any longer should put your entire existence out to pasture! Do you hear how foolish this all sounds? You say, “I am attractive and look much younger than my age, am educated, professional, and independent with varied interests.” Oh, really? Unfortunately, the
Such images CAN be a cold shower to a prospective partner.
one trait overshadowing all the others is your awful lack of dating self-worth. If you don’t feel worthy of a guy’s effort, no guy will make the effort. Girl, get ahold of your shattered self-esteem at once!

You say you want to settle down and wonder if broadcasting that is a turn-off. Darling, you can’t think about permanence when your self-image is so shaky. As my Gilda-Gram says, “Healthy love first requires sturdy self-esteem.” So you have homework to do now before considering building a future with any man later.

This is what I believe would benefit you:
  1. Avoid posting photos of you and your son on dating sites. Such images CAN be a cold shower to a prospective partner. A guy is not looking to date your son; he’s interested in dating YOU! Post only pictures of yourself. If a man wants to get to know you further, your son will eventually come with the territory — later, after you and your date have established a meaningful connection on your own. Otherwise, it’s not fair to either your child or your date to force them into a trio when a romantic duo is what you desire.
  2. Your thoughts jump directly to the idea of marriage without considering the intermediary steps required to get there. What’s the rush? S-l-o-w down! You have to get to know someone first, build a solid union, introduce your son into the mix, and then test how everyone gets along.
  3. There is nothing wrong in telling a man you’d like to eventually marry again — but don’t share these intentions during your first communications with someone! Note the difference between “Hi, my name is Remarriage-Ready Rita” and “Hi, my name is Rita, and I’d like to learn what you’re about and discover what we have in common.” Which of these two statements do you think would be more successful when introducing yourself to potential dates? Exactly.
Dating is a waterfall of droplets that seeks its rhythm and pace without intrusion. If you let go, perhaps your 51st birthday present will arrive in the form of a partner worth keeping.

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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