I have a friend. I’ve known him since I first moved here to Glasgow almost four years ago now. Our first contacts were more flirtatious than friendly, though due to various circumstances (girlfriends turning into ex-girlfriends, him hitting on various of my friends and sleeping with a few more, etc.) we established ourselves as just friends. This was more due to my insistence than his, but we’ve managed to build a good friendship over the past few years. He’s definitely messed up when it comes to relationships and the line between friendship and something-a-bit-more has blurred a few times. But for the past year we’ve been firmly just friends. I’ll admit that prior to this I romanticised our close friendship more than I should have. I held out hope for a long time that eventually he’d stop dating around and realise that we’re perfect for each other. Or even just stop all the talking and actually put his money where his mouth is. He’s made numerous comments over the years that I’m his ‘perfect partner’ and once even admitted that he’s in love with me. But still, nothing. So last year I finally realised that I was wasting my time on this guy and finally put it all behind me. I genuinely feel nothing but friendship for him anymore and am much happier for it.

So here’s my dilemma. This guy is currently dating the ultimate rebound girl. He’s now dating her for the third time, after breaking up with her twice before after he met someone else he liked better. For some reason I can’t fathom she keeps taking him back, even after he dumped her twice. She took him back again around 8 months ago and they’ve been dating since. The problem? Now he’s talking about marrying her. And I’m absolutely convinced that this is not the right woman for him. One bit of evidence being that he was basically hitting on me just a few months ago before he moved away from Glasgow. He was saying (again, by the way, this being a common thing he says when he gets drunk) that we should date someday and that we have to give it a try sometime. Oh, and that he thinks about kissing me all the time. All this occurring about 30 minutes before the current girlfriend was supposed to come and pick him up. Now, a year or two ago I would have gotten all weak kneed by this but this time, not at all. Just sort of made me uncomfortable. And very VERY aware that this is not at ALL appropriate. Which I told him and he said he knows, blah blah blah.

And please, I am aware that I’m an idiot for falling for this crap again and again in the past, but I promise, I’ve seen the error of my ways and have no feelings for this guy at all anymore. We are firmly just friends (at least I am) and I know that even though we have always had a great connection, we are not meant to be a couple. Just to be clear.

So this is my problem. Should I tell him that I think he’s making a mistake? I’m one of those people who is brutally honest with my friends and I’ve always been very clear to him when I think he’s being an ass. The way I see it, this girl is not the right one for him, or he was just being an ass a few months ago when he was hitting on me. And yes, I know, he’s not being a good friend by saying these things, but that’s a whole other issue. Or maybe, am I just being incredibly cynical? Is it possible to find love the third time around? That he got bored by this girl twice before but something this time has changed? I personally think he’s searching for stability and meaning in his life through romantic relationships and this girl has shown that she’s always going to forgive him, no matter what he does. So maybe, that IS the perfect woman for him? The thing is, the past three other relationships he’s been in since I’ve known him, every single time he said he was thinking about marriage, they broke up a few months later. Except this time he’s actually bought a ring.

I don’t know, maybe I should just stay out of it. But I feel like, regardless of our past involvement, he IS my friend. And if I think a friend is making a mistake, I always tell them. And if he thinks I’m wrong, that’s cool, I’ll never say anything again. I genuinely think he’s making a mistake though, just going by everything I’ve ever known about relationships. And yes, ok, to be fair that’s not a lot, but still. Am I totally wrong here? Regardless of this individual relationship, is it even possible to realise the third time around that this person is the one for you? It just doesn’t seem so to me, but then, maybe I’m cynical. I do want him to be happy and if this is the girl he wants, then maybe I should just leave him to it and stay out of the whole situation.

Has anyone been in this same situation?  I mean his situation or mine.  Has anyone had a relationship work after it ended twice before?  Or should I try to believe in love a little bit more?