Hi all. Long time in the game but only just found this forum- seems great with some real good advice and techniques. I have an issue for which I wondered anyone has any good ideas.

I'm going on holiday with some friends in a couple of months; I was a late addition as they suddenly had an extra space and I'm pretty close with all of them except for one girl - we'll call her robin - who is best friends with the only other girl on the trip, my friend's gf - let's call her lily.

I've never met robin but she is single, and my friends know that i just got out of a long term relationship and I think they have an ulterior motive that we might hit it off. Figuring it will relieve some awkwardness on the holiday, especially as the holidays not for two months, I added her on Facebook and she's easily an 8. My friends were saying they there will probs be a get together before the holiday anyway so I could meet her.

Anyhow, i was thinking of opening her with just a pm like "hi, it's James, Lily's friend; cheers for the accept, I figured as we're going on holiday together we should probably at least exchange pleasantries - so Hi " or something like that.

The only thing my friends have told me about her is that she doesn't have the highest self-esteem, so I'm hesitant to neg or qualify her too hard at least until we have a convo going. So I wondered if anyone has any helpful tips for starting and maintaining a convo in this situation. Or if I should talk to her at all!?

Cheers In advance.