Can a man ever date a woman who rejected them before?

I don't like to admit this, but I need help.

This woman and I go back about ten years ago. When we were young, she had a crush on me (I was about 16 and she was 15). She was home schooled and I went to a public school. We were always attracted to each other, but it didn't happen because she had a boyfriend at the time and I wasn't going to interrupt anything like that.

We've kept some form of contact over the years. About two years ago, after getting the courage to ask her out, we went on a date. At the time she was 22 and I was about 23. The first date was pretty good but I was nervous, didn't know where to take her, and overall wasn't as good as it could've been. She's not a bad chick and wanted to go out on a second date. On the second one, I thought it went well initally, but she got tired of me and I didn't do it right. I was nervous again, didn't flirt very much out of fear, and at dinner my card declined. She ended up paying for it... In fact the hibachi chef flirted with her more than I ever did. Several days after the second date, she said she didn't want to see me. I don't remember much of what she said. I apologized and admitted I didn't show her the best of me, and I broke contact with her for a period of time. Last year I got back into contact with her again and stuff is fine between us, but I've never talked down that route again.

I'm 26 and I've beat myself for it since. Over the years I've become less romantic when it comes dating, but with her I always keep wanting to come back to her. I've never opened that conversation up again, and I think maybe since it's been some time since then, I might have a shot. She's still single too. However I'm not going to try quite yet because I'm not straight career-wise and the stuff I want to do for her I wouldn't be able to do quite yet.

So long story short, is it possible to date a woman again after putting a bad impression in before?


Most Helpful Girl

  • Sure! My current boyfriend is someone I originally rejected. We lost touch and reconnected after a year, then stayed friends for a year, then we started dating.

    • what made you change your mind?

    • He matured quite a bit, and I also matured enough to appreciate what he had to offer. In other words, I rejected him in high school because I was turned off by his awkwardness and his neediness. But after we grew up a bit, I learned to appreciate his devotion and sensitivity.

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What Girls Said 2

  • You can try asking, but ehhhhhh. You have an uphill journey. You've got to make a good impression this time AND make up for whatever put her off in the past. Try and if it works out great, but if it doesn't be satisfied as friends.

  • If you think there is a spark then go ahead perfectly alright. Also you care about something let out go comes back it's yours. Maybe its a hobby of she's coming back. Honesty aligns like you love so try it can never hurt.


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