I'm almost 30 and have never been in a real relationship. Help?

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?

    • @somewhereelse
      I think it's more of a gut feeling, like she hasn't actually said "I only see you as a friend" but like one time she said she was staying in when a bunch of our friends were going out so I joked and said "you're gonna stay home and watch Gilmore girls on Netflix when you could be hanging out with me" she laughed and she also said "for the 1000th time I won't go out with you" (I never asked her out so I knew she was joking) at the time I thought nothing of it but I thought maybe that's how she actually feels.

    • I'm not so sure that your example is very conclusive. Perhaps she just wasn't in the mood to go out, but I would say that your gut feeling is more important. If you feel like that, then you are probably right in your feeling. Also, in general - if you like someone and don't feel shy around them (as you wouldn't, with a friend), I think most people would spend as much time as possible with that person, no matter how.

      Perhaps she could help you find someone who is interested in you, though? Maybe she has other single friends you haven't met yet? Dating is really hard and frustrating. I'm almost 30 as well and have had only one relationship. I kind of get the same from my male friends... "you're awesome, etc" ... yet they never want to date me either. Ah well. I think if you stick to activities that are fun for you, you can eventually find someone you find attractive and can consider as a long-term dating partner.

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.


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What Guys Said 3

  • Don't worry that much , the older women get the desperate they become

  • I think you have to just keep trying and continue meeting new people , that's the only way your going to find someone to date long term. is if you keep putting yourself out there and keep meeting new singles

  • Wow man , a guy like you must have a wife and some children.


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