I broke up with my ex about 2 months ago. We had only been together for 3 months but were friends for a year before that. We haven't talked much since then, but she has tried to keep communication up with me and I haven't been very receptive. We both share the same group of friends but they all have strong preference for me, so she hasn't really hung out with any of them lately. About a month ago she started dating someone else. The thing is, she has gone out of her way to keep him a secret from not only myself, but our friends as well. She has no idea I know about him. The only reason I know is because I felt curious one day and found out about him on her Twitter. She doesn't know that I know her username or anything, which was the only place she was even mentioning him.

About a week ago, I told her that I would be interested in talking to her about resolving our differences and see about getting back together at some point, knowing fully that she was dating this guy. She said she doesn't think it will work because she still has unresolved issues on her end (but, of course, the real reason is because she's with someone else). I told her that I understood and left it at that. Since then, we've run into each other at school and have studied together a little with our friends and gone out for drinks. During these encounters with her, she keeps bringing up the things we used to do together like vacations, and said that she would like to go on vacation again with me and another couple in our group soon. She has been giving some pretty obvious IOIs too. She also got jealous last night when another girl was flirting with me, and several of our friends noticed this as well and told me about it. Overall, she is warming up to me more and more each time we hang out.

I am 23, she's 25, and he is 19. We are both in graduate school and he isn't even in college. He keeps getting fired from minimum wage jobs. I know it sounds biased, but I truly consider him to be inferior to me in every way; he has NOTHING on me. The thing is, from what I can gather (which isn't that much, I'll admit), things are going perfectly with her new boyfriend. She seems to be happy with him. But then, why is she keeping him a secret? And why does she still seem to be into me so much? Furthermore, if I want to get back with her, what would be my best course of action?

Tonight a few people said that they noticed she's been happy and upbeat since the day I started talking to her and hanging around her again. She also once again mentioned that she wants to go back to our previous vacationing spot in New York with me. She continued to show several IOIs, jealousy, and a yearning to spend time with me. All signs would indicate that she is extremely interested in me again, but I still don't understand what the deal is with her new boyfriend. That's the only fine detail that I can't comprehend.

I've basically narrowed it down to two options:

1) She wants me back, but is waiting a little while for more "security" to make sure it'll work with us again before breaking it off with this kid. She is someone who always has to be with somebody, and she doesn't want to risk breaking it off with him if she isn't 99% sure it won't work with me. That's the way I see it, at least.

2) She just really, really, really wants to secure my friendship again. That's understandable too since I bring a lot to the table even in a friendship. But I really feel as though it's more than that at this point.

Anyway, this is a bump in hope that I get some insight.

It's tough to say, to be perfectly honest. On the one hand she's demonstrating interest by re-engaging with you and agreeing to spend time together, which at a minimum indicates she feels comfortable around you and enjoys your company. At the same time you want to be careful not to read too far into it, as only she knows her true intentions (and perhaps maybe even that's a stretch for she may be confused about things).

The bigger question is do you want her back? And, do you legitimately want another stab at a relationship with her, or do you want her to satiate your own ego knowing she's with another?

If it's the former, I suggest playing things the way you have been. If in fact she's demonstrated jealousy, I'd introduce a bit of push/pull (specifically being available to her at times, while at others being aloof, inaccessible to serve as a catalyst to a new seduction with this woman). Are there also some codependency issues at work here behind the scenes? You state that she needs the security of a relationship to feel whole, is this somebody you truly want as a prospective mate? A lot of questions abound, but it is certainly a good idea to consider these questions before further involving yourself.

On the other hand, this may be an instance of her having her cake and being able to eat it too (the security of relationship, and the tantalizing allure of having something else on the side too).

My recommendation if you want to move forth is to keep your expectations in check (as you always should do anyway), and for your own well-being put the breaks on things every now and then controlling the pace of things (a very attractive quality, and also ensuring that you're protecting yourself at the same time).

I don't think there is such thing as pure friendship between a man and a woman, let alone exes. It is possible that she's hiding her current boyfriend because of all the inferior facts you have mentioned. She is happy with him but ashamed to introduce him to people. It's obviously she hasn't given too much thoughts about getting serious with him.

It seems to me that she wants the best of both world. She wants her new boyfriend but she doesn't see and not sure about her future with him. Hence, now that you gave her an option to get back with you, she has a backup plan to fall back into if thing doesn't work out for her and him given you're more stable. She shows IOIs because she wants to keep you around.

Best course of action? Start treating her like one of your guy friend. Don't react to her IOIs and continue to game other girls. Let her know that you have other options, but you choose to get back with her. And if she doesn't hurry up and tie up her unresolved issues whatever they might be, you might move on and she will lose her chance.

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Both are very helpful posts, thanks to both of you! The common piece of advice between the two of you is that she seems to want the best of both worlds, which is a hunch that I had as well. I agree that pulling back a little would be the best thing to do for now.

If anyone else has anything to add, I'm still open to more insight.

Sometimes its best to extricate yourself from the situation (the 'third' option). This way you make a conscious decision to move on, and you out of the picture will force her to make a decision, rather than keeping yourself in a holding pattern waiting for her to decide on her next move.