So here's my situation...

[cellular887]

Hi all, this is my first post!

I made a decision a long time ago to act quicker when I had feelings for a woman. Not to wait it out so long. This was mostly due to shyness and anxiety. That's all in the past and I am much better at pacing, but this current situation has me a bit confused... and here I am taking my time again.

I have feelings for this woman. Let's call her "Jane." We're both 24. I lost my virginity to her at 21 after our friends set us up, but we were more along the lines of sex buddies after that. Soon after this, we clicked and would hang out every so often. We'd also sleep together from time to time. We were in different worlds and busy so it never became official. Sometimes we wouldn't even talk for months... Then last year, I moved and found myself thinking about her a lot. I realized I had strong feelings for her that I didn't experience before - probably because I was such a different person back then. Eventually, my work took me back home so I decided to call her up.

We got together for a drink. I was planning on asking her out officially that night, but alas, when I asked her what was new in her life, she mentioned having a boyfriend. So I put off asking her out; she still has no idea that I was going to. Then before I knew it, we were seeing her once a week and began getting closer than we ever have. We would go out with friends (the boyfriend would stay at home), she'd flirt with me, and I would flirt back. She notes how much I've changed, and sometimes we'd hold each other in public - she's right on the border of cheating on this guy with me. I'm usually very careful of the friendzone - something I'd accidentally fall into with girls a lot in high school. With that fear in mind, I became less available to her.

Then recently, we finally grabbed some dinner after about a month of not seeing each other. I was feeling antsy inside over her and wanted to test her. So I had asked how she was. She mentioned it's been a year with this current boyfriend and she's feeling bored with him. However, she also said she really likes him and wants to make it work...

So finally, my question is; should I stay the course, wait for a possible break up, then ask her out like I had planned to a few months ago? Or would it be wiser to take the initiative and ask her out now (or at least put the offer on the table)? There's obviously still attraction between us...

On a side note, I am in the early stages of dating a different girl now. When I mentioned her to Jane, things became tense for a moment. She seemed uncomfortable when I would bring up a girl...

Thanks for your time, I love the forums!

[smackie9]

Even a girl that is a friend can still get jealous. If there was any inclination of her wanting you, she wouldn't mention "trying to work things out" with her BF. In fact she would have dumped him long ago if she wanted a go with you. She's not stupid she knows you like her a lot, you don't have to tell her, she can see it.
I think you should give this new girl a try because chances are nothing will happen with your friend again. This new girl could be a missed opportunity to be with someone that turns out to be the best thing that ever happened to you. To add, all that flirting is just much wanted attention she wasn't getting from her BF hence "being bored". This is typical rebound-ish behavior.

[zertaag]

Well it certainly seems like there is definite chemistry between you and "Jane". It is usually a good rule of thumb not to go backwards in the dating world, but hey the heart wants what the heart wants!

I do have to agree with what the other poster said, if she said she wants to work things out with her boyfriend, she probably has no interest in leaving him any time soon. Picture that sentence as her way of constructing a bit of a road block.

Here are just a few things to think about:
1. Yes, she's "bored" with her current boyfriend, but does that really warrant her flirting and spending a great amount of time with another man? How would you feel if you had a lovely girlfriend who openly held another guy in public? I know that it takes two, but you don't want to be that douche who puts his hands on another guy's woman. Also, she is giving very mixed messages. She wants to work things out but she spends a lot of time with you? Hmmm...Red flag.
2. With the first point in mind, do you really think she wouldn't go behind your back when she's bored? (I'm certainly NOT saying she definitely will, these are just little things to chew on.)
3. Now, say you mustered up all of your courage and asked out another guy's main squeeze. Suppose she says something along the lines of "No, I love Joe Smith". How is that going to make you look and feel? I think that would work against the progress you made with your anxiety, because the sting of rejection is one that has the tendency to last a lifetime.
4. Just wanted to point out, lastly, that you've probably planted the seed of doubt in your current girlfriend/date/whatever's mind. I couldn't imagine dating a guy and having him say "Oh yeah I hang out with this chick I totally used to nail. She's a great girl". Just saying, if she's got a brain she's going to be watching you like a hawk. She doesn't deserve to be used while you prey on another woman.

I think that if you absolutely must obey your heart and throw it all on the line, you should do it in as discreet a way as possible. Don't come flat out and ask her to be yours, girls with boyfriends tend to react negatively to that even if feelings do exist. Tell her she's beautiful, tell her how lucky her boyfriend is. Wait for them to fight and be those brawny shoulders to cry on. It sounds dubious but hey, what you're doing right now isn't exactly the most innocent of acts .

Hope I just brought a different perspective to the table. No one on this board can tell you whether or not you should really go for it, we can just give you our thoughts and offer some suggestions. Plus, if you were to ask me, I'd say you already know what you want to do.

Good luck to you!

[cellular887]

Thank you both for your straight forward advice. Sometimes I just need to turn to others to slap some sense into me! I'll focus on who I am dating now. I'm still getting to know to her so I don't think she has any doubt in me, as long as I step back from Jane. If Jane wants me, and I'm available at the time, then she knows where to find me. In any case, the ball is in her court it sounds like. Zertagg, I laughed when I read in your post "say 'he's lucky to have you'" because I actually pulled that one to see what she would do. I said it when she was talking about how he doesn't want to go out anymore. She responded with a giggle of flattery which didn't tell me anymore than I already know.