I’ve got a bit of a problem. Most of the problem is my own doing. I’m very interested in a woman who I see on a weekly basis. She’s beautiful, funny, intelligent. She’s a little older than I am, and has a young daughter. I really enjoy being around her and look forward to seeing her. She’s a lot of fun to be around and the time I do get to spend with her seems way too short.
That’s not the problem. The problem is that I don’t know how to approach her. I SUCK when it comes to women and have zero confidence around them, especially around one I’m interested in. For instance, she likes the Lord of the Rings movies, so I wanted to take her and her daughter to go see Return of the King, but could never work up the nerve to ask her. I want to watch The Two Towers Extended Edition with her, but instead of asking her if she’d like to watch it here or if we could watch it together at her place, I just let her borrow it.
Also, I have no idea if she’s interested in me at all, and I’m afraid to push it to see if she is. The last relationship I was in ended in a seriously painful break for me. It took me years to get over it. I think I’m afraid of getting hurt again. Actually, I know I’m afraid of that. I’m afraid of getting turned down again.
It’s been over 10 years since I’ve been on a date. How sad is that? In that 10 years, there’s been only two women I was interested in. One was already spoken for, but often came to me for advice. We had great conversations that would go on for hours. That didn’t work out and she’s now married.
The second woman I tried to keep my feelings from getting out of control, so I flat-out told her that I enjoyed being around her and wanted to take our friendship to the next level, if she was interested. She wasn’t. She said it wasn’t me, it was her, but who knows if she was just trying to be nice.
So needless to say, I don’t have much self-esteem. How can I? I’m almost 30 and I still live with my parents. I can’t seem to bring in enough money to support myself and get my own place. What woman in her right mind is going to be attracted to something like that? No one I know, or have ever met, that’s for sure.
So my fear of rejection and lack of self-confidence are keeping me from finding out if she’s interested. I know I’ll regret it if I don’t do something, but I just can’t seem to get over that wall. I need help.
Chris,
I found this particular post in the most accidental way, (hello, cyberspace -that wonderful/awful thing) and that’s what emboldens me to say that you sound like such a very, very, sweet and sensitive man, that Cupid is sure to strike for you….when that fickle little cuss finally gets around to it!
Do not put yourself down. You are in fact quite a “catch,” given your good and kind heart. She’s out there somewhere; wondering where the heck you are.
I understand how you feel Chris, honestly I do. I’ve had many breakups, many rejections. It’s tough, no matter what anyone says, to approach a woman and ask her out.
The only thing I can say is that no one can tell you what to do but yourself. If you’re lacking in self-confidence, that’s ok, but if you don’t believe in yourself, then no one else is going to either. That was the best advice I was given. I’m sorry if that sounds harsh. After I heard that, I went into some withdrawals myself a while back, and man, it HURT.
But you know what, it does get better. Sometimes you just have to have faith that it will.
I just hope you don’t take it the wrong way, and I don’t really have any real advice. All I can say is do something.
And hey, keep in touch, I’ve been through quite a bit myself. I can’t give advice, but I can just listen.