I'm thinking from the acronym and situation this has to be a joke letter. Spot on advice though. Plenty of real people have strung along their SOs and could use a slap in the face through writing.

I think I dated this guy.

I'm guessing you're not all that conventionally attractive yourself, MRA

Yes.... or the guy isn't wrong that he could have a girlfriend who isn't just hot but who has the looks others find hot more than his former older girlfriend. For one thing, the ex didn't date until 27 right... that is even older than 23.

It could be his looks that kept him from getting laid or, you know, something else like his personality. Dans bet is that he is just too much of an asshole, but read the letter again:
- He dates a girl who doesn't look like a model, didn't date until 27 and then courts a 5 year younger guy she is close with and who depends on her as a friend... She doesn't sound like a happy camper to begin with. All we know is he made her cry once, possibly during the breakup, and feels terrible about it.
- He dumped someone because she was pretty but not in a way obvious to others.. after a year of fucking and dating just fine

Its great you not once made any partner cry Dan, but most of us either have done a lot worse than this guy or are not being honest with ourselfs. We are human beings with human flaws like wanted to fuck hot people more. The defining characteristic that sets apart the true assholes that that they are completely oblivious to even the possibility that they could be an asshole. Assholes always think they are awesome, otherwise we would tolerate a lot more of the mistakes we made ourself as well.

Obviously this letter doesn't fit that. Almost all of the letter is self-criticism and self-doubt.

Ask yourself this: What sort of, pardon me, social moron, apologizes for being perpetually worried about being a quote “asshole”? Only someone who doesn't yet have the social skills to realize people read over that while mentally replacing each and ever word with “BS, BS, BS, BS....” Someone who innocently and sincerely believes apologies about future behavior (staying friends or not) get taken seriously.

Why would someone who has issues (aspergers has been suggested) and finally gets laid at 23, needs the friendship and likes the girls looks and the sex just fine for a year worry about whether other people see he finally dates that skinny blond (all other attributes undiscussed) girl whose hots are obvious to everyone?

He didn't get laid until 23 while spending the, what ten years, he trying to get laid unaware of his bad looks. Ugly 18 year old guys who overconfidently overestimate their looks (IE assholes) get laid just fine. Helps if its not obviously pretty chicks who don't date until 27.

This guy staid away from people until twentysomething and was suddenly no longer that awkward 14 year boy. It really gets way better for guys in their twenties. He still doesn't go out of his way to hook up with the hot girls he wants, but there is this older someone who is “important” to him, a friend. She courts him (maybe she could not keep her hands to herself?), they end up in bed and a relationship. He knows for a year long he can do better. He knew that before they met. Only now he has a pillar of support, a friend and has seen first hand girls will fuck the guy who was an especially awkward teen after all. Now he dares to finally try courting a girl he chose himself. Someone who isn't his only older trusted friend who took advantage of his problems to solve her 27 and never dated problem.

His problem is he has to break up with his only friend, he is awkward, she isn't pretty so it they are a “us against the shallow world” couple. He doesn't want to be that guy he really really want to stay friends. He needs her pillar of support, that why he goes out of his way to write a letter asking Dan for permission.

The guy isn't ugly, he is shy (the APA calls that aspergers) and wants a obviously hot girl on his side to prove others and himself he finally can get laid. Maybe its a shy sensitive (reading the letter again, self deprecating, maybe even funny) 24 year old. Maybe he is good looking maybe he is average looking either way he is clearly smart and sensitive enough not to misunderstand whether he can do better.

He would stay with his one and only true friend but he knows what people (assholes) say behind his back about him having an older less than obviously pretty girlfriend. This reason this gossip hurts is because he is still insecure. A true asshole would not even know people gossip about him. A true asshole might even assume the prettiness of his girlfriend would be obvious to all because she is after all his girlfriend...

This is why the self confessed asshole didn't even bring up the obvious option of cheating which is the asshole move that would have “solved” his close average friend + want hot sex problem the asshole way. The reason he is breaking up, cant unequivocally say whether he finds her pretty and feels about the relationship that he treated her carelely and took her for granted is because he loves her intensely as a friend but never really had strong feelings for her. He is a guy who stays with someone he doesn't truly love for a year because of fear and worry about her feelings.

There is nothing there to say anything about his looks. Girls, especially American ones tend to be way less likely to throw themselves at hot guy than vice versa. If an American guy is hot but doesn't dare ask girls out he can stay single for quite some time. American girls will do a lot with a guy they barely met, but they will never be the first to ask for a phonenumber because that would make them a slut.

And can we get a ruling on the older woman who was a friend, a pillar of support to a really young sensitive guy. The one who instead of supporting a younger friend with some sort of issue... fucks the guy. The guy is a horny virgin to be sure and find her looks are okay but he didn't find her hot and he really needed the pillar of support from his older friend. If you reverse the genders on that doesn't the older guy with problems getting a date sound like an asshole with no regard about potentially violating the campfire rule by fucking the dependent younger virgin friend with issues?

My advice would be to be careful calling sensitive anonymous letter writers with emotional issues ugly assholes who nobody will love unless they are millionaires. Especially if their history is a pretty good fit for aspergers.

My advice to the letter writer is that relationships end and try to get to a place where both can move on.

Instead of your friend being your pillar of support offer to be hers. Consider telling her you know you were an asshole to break up, understand if she doesn't want to talk to now or ever. Obviously you have to make crystal clear you will never fuck her again and she needs to move on. But also tell her how much her support meant to you and how her friendship pulled you trough.... whatever, the letter doesn't say an I don't want to assume. Tell her to hold on to your number and that she can call day and night and that you will always be there for her if she needs a friend but not a lover/fuckbuddy. If she was your pillar of support you owe that to her.

It could be you ended up in the fucked up spot where a critical friendship ended up with fucking because you are an asshole and were thinking with your dick, it could also be plain bad luck and the universes idea of a joke.