I'd love some help in this situation as I'm completely inexperienced and don't really have any idea what to do. However, I'll start with all the back story to try and give you as much information as possible.
I met this girl in around June of '10, and after meeting her started chatting her up on Facebook via private messages. That went smoothly, and we had arranged to meet up for coffee one weekend. I ended up blowing that off after having a fantastic date the Friday before, and feeling pretty confident about that situation as to not want to rock the boat by going out with a different girl. We rescheduled - and I ended up blowing her off a second time due to being really hungover from the night before. However, third time was the charm, and we finally went out, and it went well.
After that, we kept seeing each other before we started officially dating. Our relationship was great, and I didn't have any idea at any point between when we first started dating (Aug '10) and when we broke up for the first time (Oct '11) that anything was wrong - although I should have. The thing was, when we got together I had just come out of a 'pursuit' of a girl that I was absolutely crazy about, and I dare say that this girl I ended up dating was more or less a rebound (I didn't think of her like that, but at the start I definitely didn't feel as strong as I did about the girl I had just been rejected by - not even close). So when we started dating and it was going really well, looking back I kind of 'cocooned' myself in that position in life - so even though I didn't have a job or study, I wasn't doing anything about changing it in any speedy manner because I was happy and didn't think there was a problem. Over the course of the relationship I also let myself go physically - I got complacent.
So while we were still having a lot of fun, enjoying each other's company, and things were going great, apparently she had been losing feelings for me - until I finally noticed her stop telling me she loved me in text messages, and called her on it. After having a chat, we broke up for the first time. After a few days I thought I had figured out why we had broken up - I was under the impression that I hadn't been keeping things exciting enough and that they'd grown stale. So with this 'knowledge', I messaged her and told her that I hadn't realised it was an issue, and that it was something that could be fixed. She then informed me that it was actually the job situation that had caused her to lose feelings. I told her I had no idea (while I should have known, I legitimately did not), and that I wanted to get employment for myself (half truth - while I did want a job, she was my major motivation at that point) and that it was still something that could be fixed and our relationship shouldn't be thrown away on. With that I managed to convince her to give us another shot in a few weeks time after she finished exams, which was fine with me. I actually worked pretty hard on looking for a job during that time.
In any case, we picked up dating again in late Nov '11, and I felt hopeful - things seemed fine. My biggest job opportunity came in early Dec '11, and I felt I'd get the job which would've been a big step in quelling her fears. But alas, I did not, though she seemed to appreciate my apology and my vow that I wouldn't stop until I got a job.
However, in late Dec '11 she told me that her feelings hadn't changed, and she didn't know if they would. So we broke up, for good this time. I was quite sad, but I was forced to analyse why I was sad after the break up, and realised that my life had pretty much nothing, and hadn't for quite a while, and the happiness she had been giving me had pretty much been holding me up. Realising how much life I was missing, I found a new wellspring of motivation to improve every facet of my life - and I also considered that if I still felt the same way a few months down the track, once I had everything in order I might ask her out to have a chat and try to show her what kind of person I was.
Now, the reason I didn't have any sort of 'fear' about leaving it for, say, half a year just after the break up is because my ex has never been the most 'sought after' girl. I was actually the first guy to ask her out, or even show a lot of interest in her. So I thought it wouldn't be surprising if she was still single mid-way through this year. However... about 2 weeks ago now one of my friends told me he was interested in her, and had been thinking of asking her out. I found out the next day that my ex had also indicated that she was interested in him, as late as late last year (while we were trying to reconcile). Basically, this friend is a mutual friend of ours, and after we broke up he decided to be a source of confidence for her as she didn't have too many close friends. As far as I can tell, he would have appeared as a 'safer option' for her at the time (the unemployed, overweight me vs the employed, fit him) and would have prevented our second chance from working out - after all, why bank on the promise of me fixing myself when another guy was there that didn't require it? As for him, there's no soul-mate chemistry or anything here. He's lonely, and isn't good at picking up. It's only natural that he developed feelings in response.
Since we broke up I haven't spoken to my ex. I'm still in touch with my friend, and apparently they're not pursuing anything due to the pain it would cause us (his ex is my ex's best friend >.>). I don't know precisely how my friend feels about her, only that he isn't sure enough to pursue it (he told me if he knew it was the right thing to do he would). And I certainly don't know how my ex feels - as I'm keen to win another chance with her I'm not going to risk sending any messages that could get me in hot water.
Basically, if I were to take emotion out of the equation, I'd feel pretty confident about her giving me another chance. We had a decently long relationship together filled with lots of happy memories, and the only issue that ever arose was her feelings fading due to my incompetence, which is completely understandable - a more sought after girl might've bailed long before that. I'm changing myself now, and I know personally that I'm doing it purely for myself and it's likely to stick, so, from a logical point of view, none of the bad + all of the good seems like it should work.
But then, of course, it's the emotional side of things I don't know how to tackle. I don't know how to deal with the feelings she has for this friend of mine, and how they may or may not persist even if nothing's happening between them. I don't know how to pierce through her emotions and reach a logical part of her brain that'll make her go "hang on, another chance actually makes sense now". I just don't know how to reach her.
Basically, with the way I'm living each day right now, I know ultimately I'm going to be happy. Whether or not she gives me another chance, I'll be ok. But I do know that right now, I'd like to have another shot with her - I feel like things between us are 'unresolved', as we had a great relationship that was soiled by a perfectly fixable issue, and it's incredibly frustrating that it had to come to a break up for me to learn a pretty simple life lesson (to be fair, I've had a pretty easy life where I've never really had to get my act together - until this showed me what's at stake if I don't).
So, fellow forum goers, I ask you:
1. Before finding out about the friend situation, I had initially planned on getting in touch with my ex towards the end of June, as this was my goal time period for being established in a job and being back in good shape. However, now that I know my friend poses a risk to any reconciliation, is there anything I should change about this? Should I just trust that he won't act on his loneliness?
2. I must admit that I've been reading a couple of e-books about how to win back an ex, but the few I've read thus far just haven't seemed to hit a chord with how I can approach my ex (for example, one mentioned telling your ex that the break up was a good thing and that you hope you can be friends - while the psychological principle behind it seemed all fine and dandy, it feels like it's a recipe for permanent friend zoning). Does anyone know of any publications which offer solid advice?
3. What are my chances? I'm in a fortunate position where I'm starting to develop the kind of life where if this doesn't work out I'll be perfectly fine as I know there are plenty of other opportunities out there - but more than anything (at least right now), I'd love to see how far our relationship could get with me being a proper person rather than an empty shell. I really feel like without the other guy making things difficult I'd have a great shot, but am I just being naive?
Sorry for the essay, but I wanted to give as much information as possible as I'm quite keen on getting as much good advice as possible. I'm perfectly fine with waiting to act, or acting as appropriate, but although I'll be fine if this doesn't work out - I certainly want it to work out.
Thanks for any input!