How can I help my "ugly" friend out on dates?

I put "ugly" in quotes because ugly is subjective, but by most people's standards he certainly is ugly, and he himself thinks he's ugly. And I try to tell him he's not ugly, but he never believes me, and if I'm being honest I don't disagree on him being ugly.

To start, he's not that much older than me, he's in his late 20s, but he looks much, much older than he is. Like MUCH older. Like a literal decade or more. And not for good reasons either. To start, he has a history of doing a lot of drugs, being homeless, eating nothing but junk food, never exercising, etc. And to top it off his parents were neglectful since childhood. So he hasn't been taking care of his body at all his whole life. So he basically looks like he skipped all of his 20s and 30s and jumped straight into his 40s or 50s or some shit. Looking at him you'd think he's a middle aged man.

He's bald, his skin is all wrinkly, he has a big red nose, his teeth are all fucked up and rotten, he has constant bags under his eyes, he has weird spots all over, and he's at least 200 pounds overweight to top it off.

Not even trying to insult him, by the way. He himself has stated this many times, as well as many others around him.

But his personality is the worst thing. From what he's told me he's never been diagnosed with anything, but he seems to have autism or something, because his social skills are so bad it's sad.

Like he'll find an attractive woman and go, in a sing-song voice: "Heyyyy prettyy gurrrlll! I'm Cecil! I like to yank off my eyelashes one by one and make millions of wishes!"

And yes, he has said exactly that. He's obsessed with pulling off his eyelashes for some reason.

So I wanna help him so bad. And he has asked me to help him. But I don't know where to start? Like literally, no clue. There's so much work to be done both in terms of his physical appearance and his personality. Like not trying to diss him, I wanna help him and don't know how.

How can I help my "ugly" friend out on dates?
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