Very Messy Situation

Just under 3 months ago my girlfriend of nearly 3 years and I split up. She was still absolutely in love with me but for whatever reason I was suffering from a period of mild depression and shut her out. I wasn't communicating with her and she wanted to help me but I just wouldn't talk about it. Eventually it got to the point where she was in tears all the time and made the decision to leave me. I have since got counselling for my issues and am feeling well again. We continued talking every day since the break-up and have spoken several times about getting back together but I think I hurt her so badly that she won't come back. I respect her decision on that as I acknowledge it was my actions that caused the break-up and left her feeling devastated.

Now things are starting to get messy though. Approximately 6 weeks ago she starting texting my best regularly - they knew each other before (we all work in the same large office) and used to chat at work but never any contact outside of work. One day when my mate and I were out having a drink he mentioned that my ex had text him and I thought nothing about it. At the time he had a thing for a particular girl which was not reciprocated - he is 30 and has never actually had a serious girlfriend in his life and didn't cope at all well with the rejection - he was in tears after she knocked him back even though they had never yet been on a date together - he had liked her for around six months and never done anything about it - he just let the feeling become stronger to the point he was setting himself up for devasation. My ex helped him alot through that process (as did I) and my ex and I talked about it several times and she said she mentioned in passing that this girl just didn't find my best mate attractive (he is 6'3" and weighs about 65kg so is very skinny). My ex also mentioned to me that she could understand why the girl didn't find my mate attractive as she didn't find him at all an attractive man either.

During my break-up I told my best mate absolutely everything that was going on - he knows as much about my ex than anyone as he went on the break-up journey with me. He was my complete confident.

Over the last 3-4 weeks the communication between my ex and best mate has increased and it is obvious they have become close. I never got worried about it and took comfort in the fact she had mentioned in the past that she didn't at all find him attractive. On a few occassions she actually blamed my best mate for runining our relationship as I was talking more to him and than her and wanting to spend time with him. Alot of the time I spent with him was actually me using him as a sounding board for relationship issues.

I found out via a third party that about a week ago they had met up and was told they think there is something going on between them. I confronted her about about it initially and she denied it but did confess that they had become very close. I asked her to pull back on there being so much contact from him and she said she would but I know her well enough to realise she was just telling me what I want to hear.

The next day I spoke to him about and he told me I was being silly and had nothing to worry about. I asked him to promise me that and he wouldn't actually do it or look me in the face. He undertook to pull back from the contact too and I asked him if he had feelings for her. He said he didn't know and was completely focussed on this upcoming 7 week trip to Europe (he leaves in 10 weeks) and is not looking for a girlfriend. I tried to explain the whole rebound thing to him but having not every been in a relationship didn't even know what the term went! I asked if the contact was only texts or if there was phone calls and meeting up too. He lied to my face and said no only texts and chat on emal at work. I knew about them meeting up in person a few days earlier and he has a work phone and I checked his phone bill and there had been severeal calls of 1-2 hours late into the night from his phone to her number. On several occassions it was nights where I had been out drinking heavily with him earlier that night.

It was not by ethical means but I managed to find out that they met again for dinner two night ago and then spent half an hour parked in an an empty street in a new subdivision - I assume to be intimate as he has a flat mate than I know well and she still lives with her parents.

The complication for me is this guy is my best mate, we work together as close as you possibly can, we recently purchases an investment property together which is due to settle any day, I am joining him in Europe for two weeks of his holiday and then we have a further holiday on an island booked together (with 1 other mate) the month after he gets back from Europe.

I can deal with the fact she no longer wants to be with me given the previous 6 months together - that is my problem and I am coming terms with it. But I feel absolutely betrayed that my best mate could hook up with my ex girlfriend when I have told him so much about her and what went wrong between us. And to lie to me about seeing her makes it worse. I had said to him in our discussion last week that promise me if something does happen that you tell me and we deal with it.

I am very worried for him as he has not ever been in a relationship before (any intimacy with girls for him in the past was just very drunken sex). I think he is going to get hurt from all this as I think either intentionally or unintentionally she might be trying to get back at me. I might be wrong on that. Nevertheless I don't want to lose my best mate and all the fun times we have planned in the next four months.

What do I do? I am struggling to sleep at night as it just all keeps ticking over in my brain!

Bro,what you need is a complete reality check and to audit your values.
You still keep calling him "my best friend" ? Friends dont do that,let alone the best one.
Out of the picture but dont hurt him,just let him go in a calm way,he aitn worthy (never fight for a woman who betrays you!!).
As for her...I rest my case.

p.s- I can understand you confused and all that but man up and see things for what they are.

Hmm, this is not a good situation...
If your friend start to date your ex, would you be ok with it?
If not then, you really need to talk to him and say to him that you don't want to lose friendship between you and him over this.
Ask him to tell you the truth about what is really going on between your ex and him.
He needs to decide either its you or her... (if he is really interested in dating her)
But you really need to open up and talk to him.

Even though your ex said to you while your with her, that he isn't attractive men......... well these things can changes after they get to know each other. (Since they been talking lots, they are getting to know each other well and she may like his personality or their personality matches? She may like his sense of humor.)
Since personality is number 1 priorities.
One of my good friend, she is now engaged to her bf... maybe 1 year after they've been together, she told me that, she doesn't find her bf physically attractive and even said to me that he is ugly....BUT she is falling in love with him because he has great personality and they've been together for 3years and now engaged.
Or like you said, she might be trying to get back at you?