I care about you: Come out of the closet!

I care about you: Come out of the closet!

Tell them you've come to realize that he's a homosexual.

(this could work for gay guys also, you'll just have to do some flipping).

 Tell them this as decisively as possible ("You just do, I've always noticed it but thought it was just one of your quirks").

Props if you can think of specific details ("Your favorite Simpsons character is Duffman! He's got the biggest animated crotch...").

Even more props if you claim his masculine tendencies are him overcompensating ("I think you spend time at the gym because you like other guys checking you out.")

 Again, do this as SWEETLY as possible, as though you were talking to a closeted friend you cared for that you wanted them to come out so they could finally be happy.

Bring some pamphlets.Tell them you'd be willing to hold their hand as they come out to their friends and family. Remind them of the your real gay friends, and how much happier they look now that they've come out (or how miserable they are staying in the closet).

You might even be able to set him up with them! You could all go on a double date to go see Jersey Boys.

 Do not under any circumstances act like you're being vindictive or homophobic, and don't try to rub it in for too long, because inevitably your act would catch up to you.

You'll do way more damage if you leave him to his own self-doubt, taking account everything he's done in his life, thinking that he'll be doomed to spend his life having women think he's off limits because of some aura he just exudes.

Of course, the irony of all of this would be that he turns out to be gay after all. In that case, you may have just saved his life. And then you'd be a hero, and you'd get a great shoeshopping buddy!

p.s. - Let me disclaim myself one last time, the theme of this insult isn't to be homophobic. It's to make a guy think that all their own affectations would keep them from ever being attractive to wome, NOT to make the guy hate himself because gays should be hated.