I'm quite particular about who cuts my hair and cautious about who comes close to my head, eyes and ears with scissors or a trimmer.
I've had the same 'hairdresser' for what must be 20-25 years. She's a few years younger than I am but must certainly be in her late 40s/early 50s. She's always been very cute and doable, perhaps even more now at her current age, and I've often wondered what it'd be like to give her a ride...and vice versa. I'm thinking it'd be pretty good given her attitude.
But I've refrained in asking her out for a date, or more, for fear of spoiling our relationship and ending up having to find a new 'hairdresser'. Finding someone your confident in and comfortable with is rather difficult, IMO.