I'm Dating a Guy Who's Insecure About His Hair

What Would Jessie Do? | You Have Questions, We Have Answers: I'm Dating a Guy Who's Insecure About His Hair

I'm Dating a Guy Who's Insecure About His Hair

"Dust in the wind..."

Hey Jessie and Kyle, I recently started dating a guy who's insecure about his hair, and I wanted your opinion. First of all, he's not bald. Second of all, he doesn't even LOOK like he's losing his hair. So I'm not sure what the problem is, I just know that he's always making self-deprecating remarks about his hairline. His older brother and his father have receding hairlines, and he's always talking about ways to prevent it. He won't even wear a baseball hat, because he's worried it might affect his scalp! The thing is, I don't care either way. My problem is his insecurity and vanity about it. It makes me wonder how he'll deal with REAL problems if we ever get serious. - Carly, 28

Jessie says: Maybe all the recent news about Donald Trump has your guy freaked out? Seriously, what is that thing on Trump's head. Wait, I know! Because he just revealed his secrets in Rolling Stone. Allow me to summarize: Trump NEVER dries his hair. He lets it dry by itself. That takes an hour. And, it's not a comb-over, "it's a little bit forward and back." Whatever that means

The point is, the biggest stuffed-shirt in America is so insecure about his hair, he doesn't dry it after a shower, in case one precious strand ends up on the towel. Then he combs it forward and back...but it's not a comb-over? Come on, this guy has billions, a supermodel wife, and helicopters with his name on the side, but he still clearly spends a ton of time pretending he's not losing his hair. He's insecure about it.

My point is, if a rich guy with everything is that insecure, there's something going on here. Some men just equate having hair with having confidence. But what they don't realize is, projecting confidence means NOT bitching about superficial stuff like your hairline. Just roll with it, guys, and we will roll with you.

Kyle says: Poor Trump. He needs a boost. I know...he should yap about running for president for weeks, based solely on two things: Obama wasn't born here, and Obama's not tough enough to deal with our most intractable problems. Then he'll be up in the polls, and he'll feel great about himself! As long as Obama doesn't simultaneously prove he was born here, and deal with one of our biggest longstanding problems. Then it's back to obsessing about his hair...

Jessie makes a great point - confidence is one of those things you can just smell. If a chubby dude doesn't care about his weight, he's practically invincible. And adorably chubby. But if he makes too many jokes about his weight, in an obvious attempt to address the issue, it comes off as desperate. Like a comedian onstage in a flop sweat, who knows he's bombing. Like Roseanne Barr said: "If you're fat...just, like, be fat and shut up. And if you're skinny EFF you!

Same thing with hair. It's a sensitive topic for guys, and I'm surprised women (Jessie) aren't more understanding, since you ladies spend so much time on your presentation. Carly - try to feel your guy's pain a little. Let him know you don't give a crap what he looks like. Then maybe he can feel a little more secure, and let go of the issue. Because I guarantee he's bringing it up as a way to see what you think.

Let's hear from the ladies. Is great hair really that big a deal? Wouldn't you rather your guy go Diesel than raccoon-headed Trump?

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