I get my hair cut about every 6 weeks. It's short, and it seems the shorter the style the quicker it's sticking out all over! I love longer hair, I just don't have the patience to deal with long hair.
Sounds like my wife. She had long hair when I met her, cut it short after we got married, and has never successfully grown it out since. It reaches a certain length, and it sticks out too much, and she just can't seem to do anything with it. Then she goes back and gets it cut again. She buzzed it for a while, and she has mentioned a couple of times how nice that was. Get up, take a shower, towel off and get dressed. It was quite a convenience after we had Rowan, and she just didn't have the time for grooming. Once every week or two, I'd give her a #2 on top, blended to a #1 back and sides. To be honest, of all the looks she's sported, that was my favourite. Suited her face, her jewellery, her clothes perfectly. Of course, then she got a new job and didn't want to look too unconventional to start, and four years later she's still fighting with her hair.
Is it any wonder I shaved mine off when I was 22 and for the most part, have stayed bald ever since. Hair is overrated.