I'm almost 30 years old and I've never been in an actual relationship. I've dated here and there but nothing ever stuck, nothing ever long term. I can continue using these dating apps but honestly I'm so jaded by them, a few dates here and there or a one night stand can be fun but in the long run it sucks. Now there is a girl who is a friend (not a close friend) who I'm interested in but I feel as though she doesn't see me in that way. Do I ask her out? How would I even ask out a girl who's a friend, strangers and new people are easy, they say no and it's cool you move on. A friend is different, I'll be reminded of that rejection every time I see her. Do I continue to look for something in the empty world of online dating? Thanks for listening, any input would be super helpful.
Most Helpful Girl
Is you feeling that she may not be interested in you based on anything specific, or is this more of a gut feeling?
If it is the latter - would you regret it more to never have asked her out, or to potentially make the friendship awkward for a while? Would it make your friendship awkward if she said no?
I have been the girl to turn down friends a few times - and it has sometimes impacted the friendship. Some faded out of my life over the years, not sure why, others are still my good friends and it has not really changed anything.
It's a hard one when it is a friend. I know it sounds childish - but do you have any trusted mutual friends who could possibly help you find out?
Most Helpful Guy
I feel you, brother! I'm sailing in the same boat! I'm almost 30 as well, but haven't been in a relationship for over 5 years now. Have only been in 2 relationships ages ago, and they didn't last beyond a few months. I don't actively pursuing women (I never actually did this earlier too). If I somehow find a woman who I like and she like me as well, I'm sure as hell gonna MARRY her. If not, I don't mind being single all my life.
You need to ask this girl out. But if she turns you down, be prepared to cut her off from your life, and lose the friendship. This is certainly a better option than feeling intense emotional pain every time you see her.