She's never had a boyfriend, and I'm not quite sure what to do?

I've been seeing this girl off and on for the last couple of months. She's a 25 year old school teacher, and has been traveling in spurts throughout the summer.
We started going on dates about three months ago, and total around 10 dates as of now. We're both very compatible, and I haven't felt this way about a girl in a long time. With having so much in common, the conversations never being dull, and both doing well in our careers. I've wanted to ask her to actually be with me. However, there are a few problems.
She has never had a boyfriend, and she hadn't had sex until she was 23. When she told me that she went overboard with experimenting around a lot within the last two years. She explained how she slept with a lot of guy friends/friends with benefits kind of situations. I hadn't known about this until our last date, and now confused as to what to do.
I'm very level headed, not jealous at all, logical, and empathetic in general. So, this didn't truly turn me away, but causes me to think that a relationship may be impossible. She has expressed how much she likes me, and always wants to go on another date, but am I'm foolish for continuing? Am I just setting myself up for disaster? I honestly think I am, but she fits my wants in a girl to a tee, and I'm distraught about what to do.


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Most Helpful Girl

  • That's good you haven't judged her based off of that. I was kinda similar too. It just seemed like the guys I liked wouldn't commit to be for some reason. It's much easier to hook up. I wanted a relationship but just couldn't find the right match for me.

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    • It sounds like you've been through this, and are spot on. As I kind of get that same feeling as well. What eventually got you out of that stage?

    • Not sure. Possibly just finding the right match, getting along, enjoying your time together so that you only think of each other and nobody else?

What Girls Said 3

  • This doesn't seem like a difficult decision to me... Ask her out. Maybe she's insecure about the fact that she lost her virginity late so just wanted to inform you that she's not completely incompetent. She likes you. I'd bet she's waiting for you to ask her to be in a relationship. The fact that she has never been in a relationship before shouldn't stop you from asking her out (everyone needs a first relationship), however, if she has mentioned that she doesn't want one now that's a different story.

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  • To be honest, I don't even know why she told you that. I wouldn't judge her based off of that, because sometimes people run into situations when they are to busy to have a relationship and maybe that was the time she was going through that. If you took this young lady out on 10 dates and you enjoy her personality, company, and conversations, then I wouldn't see anything wrong with waiving that part of her past.
    I think that you should maybe give her a shot.

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    • I'm glad she was open with me about it. It definitely caused me to turn my head a little, but I think you're right in giving her a shot. It'll be up to her to see if she can be monogamous though.

  • Are you worried because of the fact that she's never had a boyfriend, or that she's been "experimenting" a lot for the past 2 years?

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    • I'm more worried about her ability to be monogamous or not. With her having consistent FWB's over the last 2 years, and never having a boyfriend. I'm in hopes that if we do decide to start a relationship. That she can adapt to monogamy,

What Guys Said 1

  • I can see how you feel she might be ready for a relationship. My last relationship was very similar to this situation. I would try my best to gauge if a relationship is really what she wants. If she wants one I'd approach it slowly and not get over invested too quickly but I feel you're already at that stage. If you're there gauge her commitment, dependence, and trust with you. Have a talk about exclusivity maybe. For future reference bringing up someones past sex life is just asking for trouble.

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