Or rather, having a hairdresser do it for you. I'm almost certain I'm going to do this, so I probably shouldn't be starting this thread.

But anyhow.... experiences? Regret? Is it kind of hard to maintain short hairstyles (as in, not having it fall completely flat)? When you make an appointment, is it worth asking if there's someone particularly experienced with cutting hair short, or is that kind of insulting?

Still unsure of the likelihood of leaving the hairdresser and sitting down in an alley to cry. But I should do it anyhow, right? I haven't been to the hairdresser in a year and a half. Scary, scary places.

Oh, and if anyone knows any good hairdressers in York or Leeds or nearby places, please tell me.

General plan is short / asymmetric / androgynous with very, very short on one side and then sweeping over slightly longer on the other side. But people who pull off those kinds of looks tend to be taller and thinner and have better skin than me, so idk. And I've never had my hair above chin length, so I wonder if I should get a short bob / generic short haircut before doing anything more radical to test things out a bit. But I can't really afford two cuts, and I don't want a short bob, so... (basically, tell me to stop angsting and go cut it off).

Fell free to make this a haircut dilemmas / horror stories thread.