My Son Is Kind, Successful, Attractive—and Always Single. How Can I Help Him Find a Girlfriend?
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“I swear I’m not biased, but my son is a catch. He’s attractive, kind, successful, loving and thoughtful. He has a great job in the city and really supportive friends. But at 28, he always seems to be single. I’d love to help in any way I can, or maybe aid with his online dating profile. He says that his singleness is ‘not for lack of effort.’ Can I step in? Or should I butt out?” 

Your desire to help is the sweetest, and I can tell what a great parent you are just from your note. That said, I want you to understand the world of modern dating before you jump in to ‘help’ your son (whom I’m sure is a catch!).

Dating apps have created an over-abundance of options, which can make even the sanest of single people go nuts. Whom do you choose? When do you stop? Is playing the field wise, or is it overstimulating? 

Your son has probably been “ghosted” more times than he can count, or perhaps he’s been “zombied”—with partners coming back from the dead after several weeks of no response. He is probably “orbited” by his exes on social media, constantly reminded of all the maybes that didn’t pan out. (They rejected him IRL, but “like” all his photos. Fun! Right? Ugh.)

In short, it’s a rough landscape. If your son says his problems are not for lack of effort, believe him. And know that what’s meant to be helpful can sometimes come off as condescending and out-of-touch. So, resist the urge to give too much advice, unless he asks for it directly.

Still, there are some things you can do to support your son in his dating journey.

Ask him if he’s open to a setup

If you have friends with children roughly his age, and you think they might be a fit, don’t assume he’s not into it. After a few years in the dating pool, most 20-somethings I know have warmed to the idea of a setup, especially because there’s a better chance of success. Definitely don’t force anything on him. But if he likes the idea, you can keep your eye out for any potential partner that comes into your orbit organically. 

Be a listening ear

Resist the urge to offer advice, unless he’s looking for specific feedback or perspective from an older, wiser human. But ask about his dating life from time to time. Let your son vent, offer up your own experience, but do not give advice unless he explicitly asks for it. (Yes, even if you know he’d get more dates if he changed that profile picture.)

Don’t glamorize coupledom

All signs point to your son wanting a relationship. But make sure he knows that being single is just dandy, and he doesn’t need to find a girlfriend in order to keep you happy. (You’d be surprised what kids will do for parental approval.) And remember: We find love when we’re ready to find love, not when our mothers start freaking out about it.

Jenna Birch is author of The Love Gap: A Radical Plan to Win in Life and Love, a dating and relationship-building guide for modern women. To ask her a question, which she may answer in a forthcoming PureWow column, email her at

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