My mom has barely tried dating in 30 years. How can I help her find a meaningful relationship without being pushy?

Dear Wayne and Wanda,

My mom is in her early 60s. She’s been divorced since age 30. She briefly dated one guy after the divorce and that was it. She never tried dating again. I was young when she and the man broke up, but I think he ended things and maybe returned to a previous girlfriend.

I know for many years, she was concerned about raising us. But we are now all officially adults and out of the house.

She’s a lovely woman — smart, independent, funny. I also think she seems lonely. I recently brought up dating and she got very defensive.

She basically said she has plenty of meaningful relationships and is fulfilled and at this point in life, doesn’t need to date. Granted, she has a fulfilling career and great colleagues but she doesn’t really have girlfriends and her social life seems pretty work-based.

I personally think she’s avoiding dating because she’s insecure and she’s wasting time when she could meaningfully connect with someone.

This is a really weird conversation to have with my mom but I don’t think anyone else in her circle would. Am I overstepping or does she need to hear this?


Wanda says:

My mom has a phrase she loves to level at me when I seem to topple the social order of things and attempt advice-giving: daughtersplaining. As in, “Stop daughtersplaining me. I’m older and wiser and don’t need my kid to attempt to tell me what’s up.”

It’s an awkward imbalance, potentially, when we see areas where our parents could possibly be happier, healthier, more fulfilled, and yet we feel cowed by self-doubt because, after all, what do we know? These are our parents!

And what we think and have to say — well, it could be wrong.

Then again, it could be right.

What’s the harm in asking tough questions, if we do it with compassion and sensitivity? And to your point, if we don’t, who else will?

Your mom might be happily ever after with her life, or she might be happy enough after all the stuff she’s dealt with. And it might take a couple uncomfortable rounds of questions to discern the truth. The good news: as her child, you have an unconditional love pass to ask the tough questions even a couple times, even if you’re being annoying. If you’re genuinely concerned her insecurities are blocking potential opportunities, don’t give up just yet.

Wayne says:

Modern dating is straight-up crazy with its hook-ups and letdowns, ghosting and gaslighting, obsessing over apps and playing the field. Now imagine diving into that singles dating pool after 30 years out of the game. Your mom would be lost in the wild in the best-case scenario. She’s no fool, so it’s no wonder she’s hesitant if not full-on resistant to the idea of dating again.

Dating, and putting yourself out there to meet potential partners, is a lot of work. Relationships are even more work. Raising kids, yep, the ultimate work. Going through a significant split with kids — some of the most exhausting and depressing work ever. Your mom has been there, done all of that. So maybe she has a clear heart and mind regarding what she does and doesn’t want out of the relationships in her life. And her being your mom, you have to respect her on that.

But you love her and you don’t want her to be lonely, and you do have a different perspective on life and love, which she should respect, as well. So find a middle ground in which you and her can ease out of her comfort zone and routine. I’m not talking about dragging her out to the club and hitting on every dude on the dance floor. More like getting her into low-pressure, high-quality experiences; things you’ll both enjoy while simultaneously broadening her world. Weekend road trips. Art outings. Hikes or bikes. A new restaurant every week. Whatever. If mother and daughter have a good time together — excellent. If she discovers a new hobby or passion, meets new people, or makes a special friend along the way — bonus.

Just don’t force the dating thing or she’ll shut you down, which is frustrating for you both. No point. She’s made it clear. Better to instead maximize your quality time with her and find ways to help her live her best life. For an independent person like your mom, that will make her happier than any partner can right now.

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at