How to talk to my male friend about women not approaching him (feeling ugly)?

Hi, Am lady. So I’ve got a friend who has recently been feeling down because of two conversations he’s had with some women at his work (early to mid-twenties crowd).
First conversation ends up with this girl calling him “nerdyâ€, which he says “normally means unattractive, undesirable, and not seen to have a sexuality.†I’m not gonna disagree with him on that. Conventionally, that’s what it means. Second conversation he had a couple of the women talk about how this guy, who’s obviously a ********* and womanizer, is cute or whatever. He gets sad, says “but that guy’s a ******, anyone can tell he is, but he’s seen as more desirable and is invited to things while I’m stuck here as a nerd.†I get how he can feel that way. Here’s the thing. He isn’t unattractive. He’s from Central Asia, so he’s brown and has coarse hair, and glasses. But all in all he’s not an unattractive guy. He and I got in a heated discussion where basically I was telling him, “women don’t approach men. That’s just a thing,†and he replies “easy for you to say, I never hear any stories of anyone ever finding me attractive, but I’ve heard it about you (me)!†Also, he used to be called ugly a lot in elementary and middle school. Basically, I don’t know what to say. He says he doesn’t doubt that I find him totally boneable, but ultimately I guess his insecurities don’t come from just “being attractive to someoneâ€, but being seen as worthwhile in society.
I’m having a hard time figuring out what to say. I’ve never had to deal with feeling ugly, sure, a few insecurities and imperfections, but I fit into “mainstream†beauty, and have forever. I can’t relate to him at all. I have no idea what to do.
TL;DR: My friend isn’t conventionally attractive and he thinks people value him less because he isn’t what society considers to be “handsomeâ€. Probably a lot to do with his own insecurities, but they’re still very real.


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