I Have Low Self-Esteem. Is Online Gay Dating For Me?

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Reader’s Question: Is online gay dating for me? I’m a 40-year-old single gay guy with average looks and great sense of humor but have been overweight for years. I’ve been fat-shamed by family, friends and boyfriends growing up and have extremely low self-esteem. I was also the brunt of a very cruel fraternity prank in college that I have never gotten past. It just crushed me and humiliated me.
After having two short, but painful, relationships in my 20s, I swore off dating for good. I’m no good at it, and the men I attract are cruel. One left me stranded at a restaurant because I wanted him to pay for once; one told me that he was too grossed out to kiss me … The list goes on. You honestly can’t imagine the painful things that have been said about me. And I always blamed myself. So I just said no more.
All these years later I’m wondering if I should jump back in the ring. I still have poor self-esteem and I’m still overweight, but I’m a good person. I just don’t want to be shamed or made to feel bad. I want someone to be on my team for once, and not against me. Am I too old for online gay dating? Have I been out of the game too long? Any advice would be great.

Sincerely,
40YOVirgin

Gay Dating Solutions: Hey 40YOVirgin! This is so nice: it’s very rare that I get a letter from someone who describes themselves with positive adjectives. To me this says you are at a fine starting point for potentially getting into dating again: maybe you feel that you have poor self-esteem, but your letter belies this: you do have a good understanding of the positive things that you bring to the world. Understanding these will certainly help you if you do decide you want to try meeting someone who values and respects you.
You mention a few incidents in your past that have weighed heavy on your conscious when it comes to your relationships with men; I wonder if you have ever talked to a therapist about them? If not, it might be helpful to get some professional help to work on being able to feel better about these events in your past before you pursue experiences that might trigger bad memories or make you feel unduly vulnerable.
Now, is online gay dating the best way to meet someone? It may be because it can give you the opportunity to test the water a bit: corresponding with men before you meet them to gauge your interest or enthusiasm for dating. It sounds like you have been quite hurt in the past, and because of this I’d urge you to remember to take things slowly when you start: it’s OK for your initial forays into internet dating to simply be useful in terms of the exposure that they give you to the idea of dating. Take some time to understand what you like in men and what makes you feel some misgivings. Over the years I’ve gotten much better at realizing that a gut feeling that someone isn’t quite right or kind is usually accurate, not something that I should forgive in the hopes that our interaction improves. Allow yourself the opportunity to tune in to these feelings.
As for the issue of your weight and appearance: so few people in the world fit the mold of what Hollywood tells us is conventionally attractive. And yet so many of us find love anyway. If you’d like companionship, don’t assume that the way you look will be the barrier to it. You are a wonderful person with a good sense of humor. Be forthright about these things and trust that it is possible to meet someone who loves these things, and more, about you.

Have you found the right one, or are you still searching?

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