My wife and I have a 37-year-old son who is single. He is bright, very fit, not unhandsome and broke. (He doesn’t earn much money as an actor in Los Angeles.) He has expressed frustration about dating and forging romantic relationships with women he meets on dating apps and at work. I would be happy to pay for a matchmaker for him, but I don’t know how to suggest this without encroaching on his private life or possibly hurting his feelings. Do you have any thoughts?
DAD
I have nothing but compassion for people who are sincerely looking for love and relationships on dating apps — or anyplace in a world where dating apps exist. When I first moved to New York City, long before the advent of apps, I got a small taste of what your son is up against now: On any given night, I could walk into a gay bar and see 100 faces. But how do you find the right person for a romantic relationship in a sea of people?
It was difficult — not least because I rarely stopped looking over the shoulders of the men with whom I was speaking as I hunted for better options, and they rarely stopped looking over mine. Now, multiply my experience by a gazillion, and you have a sense of what single people face today: seemingly infinite options across multiple platforms, a gameified system of swiping that’s addictive in itself and the impossibility of knowing what anyone is really looking for on the apps — despite what a bio might say!
Now, I admire your generous impulse, but you haven’t said nearly enough about your son’s difficulties to know if a matchmaker is appropriate for him. I can’t imagine you would hurt his feelings by asking: “What are the apps like for you? Do you mind sharing your experience?” The more you know, the better you can help. There are books about navigating dating apps. But I would try to understand your son’s difficulties more specifically before rushing in with any solutions.
What Silence Is Saying
Two years ago, I went on a summer exchange trip, and I met another girl during the two-week program (we are both teenagers). We became friends quickly: We texted almost every day and FaceTimed frequently. I even visited her at her home in another state. I began to notice that I was reaching out more frequently than she was. Eventually, she stopped responding to my messages altogether. I texted a few more times to ask if something was wrong. I could see that she read my messages, but she never responded. It’s been over a year since my last message, but I still miss our friendship. Should I reach out again?
TEEN
Being ghosted can be a painful experience. My heart goes to you. But I would not message this girl again. Try to accept that her nonresponse is a response in itself: She is not interested in being friends. It’s a shame that she couldn’t find a kinder way to express herself. But that’s her problem. You did nothing wrong here, so don’t blame yourself for her poor communication skills.
It’s also normal to miss people we care about. So feel your feelings — and share them with friends and family — but leave it at that. Save your valuable energy for people who reciprocate your love and support.
Compound Your Interest in Others
I am in my early 60s. I have never been a big earner, but I always invested what I could spare. I have two friends whose earnings are similar to mine, but after a bad experience or two in the financial markets, they stopped investing. Now I’m approaching a comfortable retirement, and they are looking at a darker picture. I know this because nearly every conversation with them comes around to their financial plight. On the one hand, I think: You made your choice, now live with it. On the other hand, I think: What’s stopping you from investing now? How should I deal with this?
FRIEND
I understand your frustration with your friends’ recurring complaints. But this is a serious problem for them, so some compassion seems warranted. They may not have the financial sophistication to invest sensibly. Next time, say: “You raise this topic frequently. I wish I could help, but I’m no expert. Why don’t you talk to a financial planner or to someone at your bank?” They may need a gentle push in the right direction.
And Here Come the Wallet Photos
My husband and I do not have grandchildren. Our only child and his spouse opted not to have children. Our dilemma: What should we do when we are out with a group of friends who invariably start talking about their grandkids? The conversation can go on for 10 minutes, and we have nothing to contribute.
NOT GRAND
As a person without children, I have some experience here. I have learned to practice patience in hearing parental updates, and I lob in occasional questions. I’m not uninterested in my friends’ children! But when I’m ready to tap out of the conversation, I turn to the people around me and ask about a shared interest or a novel or a television show. Works like a charm!
For help with your awkward situation, send a question to [email protected], Philip Galanes on Facebook or @SocialQPhilip on X.
The post Our Son Is Striking Out on Dating Apps. Should We Hire a Matchmaker? appeared first on New York Times.
