I’m Not Meeting High-caliber Men

It’s September. New beginnings. Let’s figure it out. Dealing with a breakup? Unrequited love? Having trouble on apps? Moving in with someone for the first time? Send a question about it to [email protected] or fill out this form. Also, chat at 1 p.m.!


I am 40 and have the worst luck with men. It’s probably not as bad as I see it, but I am so discouraged by the caliber of men I meet. I want a good man, not young-minded male who claims to be more.

My generation of men seems to have completely different values than what my parents taught me. And supposedly I’m considered attractive, yet I’ve had no luck in getting approached by attractive men.

Not to mention I also may be in love with my best friend, whom I’ve known for 16 years. But he lives in another country. And we’re not about the long-distance thing.

I am such a mess. My hope for love is diminishing and causing low self-esteem. I feel like a high school kid just starting out in dating, even though I’ve been doing this for 20 years. I’m wondering what to do.

I keep asking God for signs but it seems I’m missing them. What would you advise?

– Disappointed


You allude to your faith in this letter. Maybe it’s not a big part of your life, but if it is, a faith-based community might be a good place to meet someone who shares your values. Are you part of a local place of worship? Do you engage with the people there? Think about whether that might be a good place to spend more time.

I don’t bring up matchmakers much in Love Letters; the service can be expensive, and I never want to assume people are wiling to spend money when there are so many free apps. But in your case, I wonder if it’s worth meeting with one or two to see what they might offer. You seem to want a more formal courtship – to be approached. A matchmaker coordinates who does what with an initial date or courtship. You might like that process. Also, some of the men who sign up for the service are probably pretty serious about wanting to meet someone.

I can’t speak to the caliber of men you’re meeting, but before we start throwing around that word (“caliber”), I’d just say that yeah, some men might not perform certain kinds of chivalry, but they might be great people. Remember that even though you want to be approached, there’s an entire app designed for straight women to make the first move – to give them more control.

If you don’t want it that way, that’s fine, but the men you meet might be used to that style of dating. It doesn’t mean they’re not wonderful humans and great company.

– Meredith

Readers? Thoughts on meeting someone? What about the best friend?

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