Hairy Dilemma

I just took the boys for haircuts. As a general rule, I cut their hair short every six months or so and then let it grow out until they look pretty shaggy. I take them to Kids' Hair, which is a bit pricey, but worth the money because the boys actually enjoy going to get their hair cut. They get to watch a video in the chair, there's plenty of toys while you wait, and they get suckers and stickers at the end.

It's a relief to be so low-maintenance about the boys' hair. I've had a life-long battle with my own hair to get it to look the way I want. I have a great stylist, but I shell out big bucks for it every two months, plus all the goop I put in my hair. Josh has tended to be more like the boys, getting shorn periodically at the cheapest possible price and letting it grow until it begins to bother him. I admit that I haven't always been positive about his haircuts, hating those first super short days, but getting used to it as it grows out. Finally last year, he began to let his hair grow because I tend to be a fan of long-haired men. Now it's super long and almost always back in a pony tail (I would kill to have that gorgeous blond mane, but that's another story).

He's growing tired of his long hair. Fair enough. It's pretty long. He asked me what he should do and I suggested that he get his hair cut like another bearded super-hottie, Ray LaMontagne:

Photo

The problem? He's never actually gone into a salon and asked for a specific haircut and doesn't know where to go. Also, he will then have to get his hair cut on a regular basis and the maintenance just seems like too much work. I told him that, if that's the case, he should just take advantage of the fact that nobody really cares what a guy's hair looks like and go back to his old cut, grow, cut strategy. Somehow that's not satisfying either (perhaps because I don't ever like how his hair looks when it's first cut?). Is there some solution that we're missing here?