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I’m not meeting high-caliber men

Love Letters

Love Letters

Q. 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 a young-minded guy 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 interested in trying 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?


A. You allude to religion 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 a member 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 for romance. But in your case, I wonder if it’s worth meeting with one or two services 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 acts 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.

Men who would never dare approach you first might be wonderful humans with a lot to offer.



Based on your letter, I get the impression that you do not give a man a chance if he does not have a certain job or look a certain way. I mean, sure, we all require some level of attractiveness in the people we date and want them to have ambition. But you seem more concerned with the superficial things than dating a guy who makes you laugh, or a guy who doesn’t make that much money but loves what he does and treats you well.


You’ll never find a suitable partner if you’re already in love with someone else.



^ This is your problem. This is preventing you from meeting and/or committing to men. You are likely self-sabotaging yourself by saying they don’t meet up to your best friend or you pick men that are not right because you really don’t want anything to work just in case. Look, if there is potentially something there with your “best friend,” explore it. If not, then stop pining over him, lessen contact, stop thinking of him as your best friend, and refocus your efforts on eligible people. If you are using dating apps, I actually suggest going for someone outside your “usual” type. I never would have met my husband on a dating app — but we are going on 31 years. You want someone who shares your values and direction, not your hobbies.


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