How to approach a friend of a friend

[muso_romantic]

I’m very interested in a girl but in a dilemma about how to approach her about it. I would like people’s advice and thoughts.

She’s the friend of a friend and I need to explain a bit about the friend first.

I’ve been married for 10 years (recently separated). I have a friend (Anna) who I worked with during the first year of my marriage. We got on really well and just before she left, we kissed quite passionately after a works night out. A few years later, we met up, got very drunk and ended up going back to her place. I stayed the night, during which we had drunken fumbles and it was a bit embarrassing in the morning. I think she felt guilty at having brought me back.

We’ve re-established friendly contact again this year. She now lives in London (I live 100 miles away). I had cause to go to London recently and we arranged to meet at a bar. She brought her friend Clare along who I immediately recognised. I’d spotted her a while back on Anna's Facebook friends as being very her very attractive housemate. Obviously, you can’t go contacting every attractive girl you see on Facebook (at least I don’t!) – you can only hope that you get the chance to meet them – and so far, I’m glad I did. I should say she's much younger than me – I’m 39, she’s 24.

During the evening, most of the conversation was taken up with me explaining the ins and outs of my marriage breakdown, so not the merriest of nights. However, I did feel Clare and I had a little spark of connection – we did similar degree courses, and joked about some things to do with that, and other little signs e.g. when I mentioned something about my habits she seemed to make a point of saying how she would do exactly the same. Not much, but one does tend to cling on to these things. Overall, she left an impression on my mind as someone clever and thoughtful – just my type, in addition to being physically attractive.

While we were talking, Anna explained that I’d worked with her 10 years ago. I was surprised that Clare did not already know this (i.e. that Anna might have explained before arriving) so I assume Clare did not (and may still not) know the full details of mine and Anna’s history.

At one point, Clare mentioned to Anna that she thought they ought to go and although Anna was going to stay, she agreed to go back with Clare (pretty obvious decision seeing as they live together).

Now, here is the dilemma. How (and should) I go about pursuing Clare?

We live in separate cities which doesn’t make it easy. She may not find me attractive (she did suggest leaving, after all), and my personal situation isn’t great (kids, recent separation, no job at the moment). However, I can’t let all of those things stop me.

I could add her to my Facebook friends and gently start chatting to her, but I’ve pretty much stopped using my account for reasons to do with not liking the site and I don’t want to start it up again just to pursue her. I feel that would be being untrue to myself.

I don’t have her mobile but I do know where she works. So, I’ve thought about booking travel to London to get there for lunchtime and phoning her at work to see if she fancies going for lunch (without her realising I’m making a special trip). 10 or 15 years ago this would have been fairly normal but I realise that now this may be very over the top and stalker-ish (without first approaching online, I mean).

My main concern is how it would seem to Anna. Part of me thinks I should speak to her about it first. Not just to sound out whether Clare likes me but mainly to ‘ask her permission’ given our history and that they are friends and housemates. I don’t want to appear like I’m going behind her back. Our past events are just that – in the past – but somehow it feels disrespectful to go chasing after her mates (if you want to put it like that).

Maybe if I was just open about it, ring Anna and say “look, I’m going through this dilemma, what do you think…?” Then I'd risk being put off doing anything about it, when if I approached Clare first things might develop.

That’s pretty much where I stand. The longer I leave things, the odder it will seem, I feel.

Any thoughts greatly appreciated.