6 Reasons You *Should* Date the Man Who's a Mess

Free yourself from the world of looks-good-on-paper guy.

There's nothing like wedding season to encourage you to sip bespoke his & hers cocktails and start checking out the groom's second cousin like maybe he's The One. 

He can pull off a suit, he has a job, he probably pays rent on a regular basis. He checks off all the basic boxes of adulthood so he's worth a date, right? 

I'm here to argue no, not really. Go for the guy who doesn't have his shit together. Here are six reasons: 

A guy who's willing to forgo the 9-5 route has taken a big risk and figured out how to make it work. Remember in Knocked Up when Paul Rudd's character laments that he's unable to drop everything and go to India? Not a concern for this guy.

Marry a guy who doesn't have his shit together

(Image credit: Courtesy of Kelsey Coleman)

The guy with the checkered past (and present) has all kinds of helpful tricks up his sleeve. He can tell when the wind is picking up from that summer sailing, and he can jimmy your car door when you lock your keys inside. 

If he's managed to survive on $10 in Thailand, he knows how to prioritize. It suggests the ability to save up, live frugally, set budgets, and maximize pleasure from what little you have. Money is the leading cause of stress in relationships, so, you know, helpful to have a guy who knows how to stretch a dollar. 

Marrying the guy who doesn't have his shit together

(Image credit: Courtesy of Kelsey Coleman)

You might expect that the doesn't-have-his-shit-together guy is the impulsive, outgoing, attention-seeking life of the party. Some of them may well be, but I'm referring more to the social intelligence and empathy earned through visiting different cultures; the unending patience that comes with spending hours negotiating for freelancers' insurance; the sense of humor that's required when you have food poisoning in Ecuador. He sees the big picture and is excited about what life has to offer. 

Maybe you're a 9-to-5 girl and he dares you to play hooky and stay in bed all day (just once!), or maybe you're an intrepid adventurer and he urges you to try bungee-jumping for the first time. We all have our boxes, and we could all use a partner who points them out.

Marrying the guy who doesn't have shit together

(Image credit: Courtesy of Kelsey Coleman)

If it seems like everyone you know is going the married-at-X-age, kids-at-Y-age route, there is an exit ramp available to you. You don't want a "typical" life? Then open yourself up to a non-typical, maybe even kinda weird guy. He'll cheer you on when you sign up for drumming lessons at age 44. He'll understand when you want to go on a vacation completely alone. 

Bottom line: A messy guy is often a happy guy. And he might make you happy, too.