I am very interested in the girl that cuts my hair (me 24, her 21). I have been having my hair cut by her for about 2 years now. A few months after I met her, we were messaging back and forth on Facebook about miscellaneous things for a few days, and I asked her if she would like to go out to dinner the following weekend.
However, she messaged be back saying she was flattered I would offer, but she had just broken up with her boyfriend about 2-3 weeks prior (it was true), and wasn't looking for anything serious at the time, and didn't want to be tied down (they were together for around 18 months). She said "I wouldn't mine hanging out sometime though" I replied back saying no hard feelings, and I completely understand -- but if she's ever in town (I live in a college town and a lot of people come here to party) to hit me up.
She responded back saying she was going to be coming to my city that night. I said "awesome, hit me up when you here ill already be out and about", however she never ended up coming that night as her friends bailed on her (she was telling the truth). I never pursued her anymore after this occurred as I didn't want to come off needy/clingy/creeper. AND She did end up getting back with her boyfriend about a month later. They stayed together for a little longer, but then permanently ended it a few months later and she hasn't been with that guy for over a year now (so I can assume they are completely out of each others lives).
FAST FORWARD 18 Months:
I have continually went and got my hair cut from her over the next one 1/2 years, and everything was completely normal (no awkwardness about asking her out once, we have great conversations, a lot of similar interests, etc, etc.). I have dated a few people since then, as I'm sure she has also.. but it ends up we have both been single for the last 3-4 months. We never talk about relationship status while I'm getting my hair cut though.
Her Birthday was about 2 months ago and I ordered anonymous flowers sent to her. She posted a picture of them on Facebook and was super happy/excited to receive them. I told her in a round about way about 4-5 days later it was me (I made her put 2+2 together to figure it out), and she messaged me on FB saying "it was seriously so nice/sweet/caring of you, thanks so much!".
Well, I have had one haircut since then.. And once again it did not feel awkward or anything even after having flowers sent to her (I didn't try to make a move with it, I just wanted to send a friendly gesture to make her happy - she works really hard!).
Now that you have read my wall of text, what do you think... Do you think she could be interested in me? I am not a big fan of asking someone out twice, but due to the circumstances, I can honestly understand why she said no 18 months ago.
Edit: I am not really looking for the "just ask her, you won't know until you try".. There is a very strong chance I will ask her, but I also don't want to lose my hairstylist (hard to come by)
Most Helpful Girl
I probably would if I were you... I mean you've known her for a long time and you wrote this huge question about her, so she's obviously on your mind so why not? you're clearly interested and it couldn't hurt. But if she says no again I wouldn't try again and start to move on.