Everyone's Wingman: Fashion, Bread-Winnin', and Someone Thinking You're Gay

“Why does every man in GQ wears pants that are an inch above his ankles? Am I the only one who thinks it looks ridiculous?”

I guess that, more than anything, these photos are meant to sell stuff. I mean, you can’t buy the socks unless you see ’em under the suit, right?

“If your girlfriend comes out of the bedroom wearing something completely ridiculous, do you say something or not?”

I’ve never been one to know much about women’s fashion. My gut reaction has always been to bite my tongue. More importantly, you need to decide if you really want to suffer horribly for the rest of the night (and, let’s be honest, well beyond). If she looks bad, she’ll find out soon enough from the body language of the women she encounters.

“This woman I’m seeing is richer and more successful than I am. I like her a lot, but I can’t help but fixate on this. Any thoughts?”

There’s a universal truth that says when a man starts getting fine tail, there’s a boost to his ego unrivaled by anything else in life. Unlike getting a great job—which, when all is said and done, is still work—dating someone who is not only successful, but happy, can make you feel intoxicated. Blessed, even. Like winning the lottery or even better, finding a massive discrepancy in your checking account. You don’t know why you’re getting all that money, but you keep your mouth shut and hope no one notices.

I don’t know what any of that has to do with your question, but I felt it needed to be said. I mean, c’mon, man; that this woman digs you is probably pretty rad, right? Why go and fuck up a good thing when you can just be happy for her. She’s getting that fucking bread, dawg. Why you hatin’?

“Why is it that a woman assumes that a good-looking, clean-cut man who knows how to dress is gay?“

Because you didn’t ask her out, dumbass.