How to help a guy find a woman when he is incapable of maintaining relationships.

I got this cousin, he is about my age in his late 30s. He is not fat, not bald, not generally unattractive, blue eyes, red hair, 5'11. His family is comfortable. Not super rich, but his pops drives a new Ferrari and he got a Mercedes at 16, drives a Porsche, had a Rolex in high school, definitely a super preppy guy in his youth. Mother absolutely doted on him his whole life, I think the parents pay for just about everything indirectly. He works for his dad managing properties. He doesn't lack time or money. He moved out of his parents place in his early 30s. He is close like a brother, so I just can't help but wonder what went sideways in his brain. I can't have this dude being the 5th wheel when I am in my 60s.

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Why is he perpetually single? I mean, seriously. Hasn't had a consistent girlfriend since college, that's almost 20 years ago. Nothing lasting 3 months that I can even remember. Does having a smothering parent ruin your chances of being in a meaningful relationship? I have never had an problem meeting girls, dates come easy because I just ask and some of them say yes. So I have (luckily) never been single more than a month or so. This guy also doesn't seem to make new friends in life. I have so many rewarding friendships with new people and old people. I am not super outgoing, but my friends pull me into events, I try new things, even when I'm not so good at it. I go on group trips with friends, I do stuff. I play league sports, I think relationships you have with people are more valuable than material things.

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So I arranged for him to run into this great girl I know. I dated her friend, which kinda makes her off limits in my circle of friends, but she is definitively his type, or maybe the type he has always dated? I always think of her when he comments on finding someone. A little bigger girl, giant rack, attractive face, etc. Also, she is brilliant, makes serious bank, and is super outgoing. I thought it was a home run. They date for maybe a month and it fizzles out.

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I run into her at a party later on and I tell her that I'm sorry that it didn't work out, I really liked her for him. Then she drops the bomb on me and she tells me he is "flaky and cheap." How does a guy like that have an excuse to be flaky with such an awesome girl? She got married recently to a pretty cool guy, and I keep thinking about how great it would have been had my cuz not botched that one. How does a guy with plenty of cash come across as cheap? And flaky too? I get the vibe that he always keeps his options open till the last minute, which I hate, but who does that with the girl they are actively dating? Maybe he is just incapable of relationships? Is that a thing?

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We tell people all the time that they are single because they are fat or unattractive, but some people are just incapable of maintaining a relationship.

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Anyway, I found my brother a bunch of dates on Match, I wrote his profile, picked his photos, set up the dates. One really liked him, they are happily married, amazing girl. I don't know if I can do it again a decade later. I am wondering if I should push the cuz into OLD dating or encourage him to seek therapy. He is almost 40 and his mind is still stuck in high-school while his high-school friends have pretty much all moved on with work and family.

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What would you do?

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Edit: He asks me to help him on a regular basis.

Submitted May 17, 2019 at 03:18PM

I got this cousin, he is about my age in his late 30s. He is not fat, not bald, not generally unattractive, blue eyes, red hair, 5'11. His family is comfortable. Not super rich, but his pops drives a new Ferrari and he got a Mercedes at 16, drives a Porsche, had a Rolex in high school, definitely a super preppy guy in his youth. Mother absolutely doted on him his whole life, I think the parents pay for just about everything indirectly. He works for his dad managing properties. He doesn't lack time or money. He moved out of his parents place in his early 30s. He is close like a brother, so I just can't help but wonder what went sideways in his brain. I can't have this dude being the 5th wheel when I am in my 60s.​Why is he perpetually single? I mean, seriously. Hasn't had a consistent girlfriend since college, that's almost 20 years ago. Nothing lasting 3 months that I can even remember. Does having a smothering parent ruin your chances of being in a meaningful relationship? I have never had an problem meeting girls, dates come easy because I just ask and some of them say yes. So I have (luckily) never been single more than a month or so. This guy also doesn't seem to make new friends in life. I have so many rewarding friendships with new people and old people. I am not super outgoing, but my friends pull me into events, I try new things, even when I'm not so good at it. I go on group trips with friends, I do stuff. I play league sports, I think relationships you have with people are more valuable than material things.​So I arranged for him to run into this great girl I know. I dated her friend, which kinda makes her off limits in my circle of friends, but she is definitively his type, or maybe the type he has always dated? I always think of her when he comments on finding someone. A little bigger girl, giant rack, attractive face, etc. Also, she is brilliant, makes serious bank, and is super outgoing. I thought it was a home run. They date for maybe a month and it fizzles out.​I run into her at a party later on and I tell her that I'm sorry that it didn't work out, I really liked her for him. Then she drops the bomb on me and she tells me he is "flaky and cheap." How does a guy like that have an excuse to be flaky with such an awesome girl? She got married recently to a pretty cool guy, and I keep thinking about how great it would have been had my cuz not botched that one. How does a guy with plenty of cash come across as cheap? And flaky too? I get the vibe that he always keeps his options open till the last minute, which I hate, but who does that with the girl they are actively dating? Maybe he is just incapable of relationships? Is that a thing?​We tell people all the time that they are single because they are fat or unattractive, but some people are just incapable of maintaining a relationship.​Anyway, I found my brother a bunch of dates on Match, I wrote his profile, picked his photos, set up the dates. One really liked him, they are happily married, amazing girl. I don't know if I can do it again a decade later. I am wondering if I should push the cuz into OLD dating or encourage him to seek therapy. He is almost 40 and his mind is still stuck in high-school while his high-school friends have pretty much all moved on with work and family.​What would you do?​Edit: He asks me to help him on a regular basis.