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Well I went ahead and booked the trip anyway. Might be a dumb move but I think I have a real shot at this, wanna see how it goes. The trip is the main thing for me anyway, it's not the end of the world if I can't bring any chicks to the room. I should mention that the place we're going lies outside of phuket and is pretty secluded with our own private beach (there aren't even any bars there). We will be by ourselves mostly. She's been super excited to go there and she has hinted several times that she doesn't want me to bring any chicks back to the room. I take that as a good thing because I don't think she knows I'm interested in her as I haven't exactly been chasing her. Also she has asked about me quite often from our mutual friend. Mixed signals perhaps but maybe I just haven't been clear about my feelings towards her.
I know it will still be a great trip as she's a fun person, and I'm not head over heels for her so I can live with it if it doesn't work out. I hadn't planned on going full out and trying to seduce her right away anyway, thought I feel the water a bit first. But you're bound to bond if you're sleeping in a double bed for 2 weeks and doing stuff together in a very romantic setting.
NOOOO!!
You said it yourself "I just haven't been clear about my feelings towards her."
That's it! She's going on this trip with a friend!
What you need(ed) to do was have a make or break moment. Ask her out, make a move. If she reciprocates, AWESOME! You're going on this trip with a hot date. If she doesn't, cool! You get to game freely without a built-in cockblock.
But now she's stuck to you, there is no freedom to make a move regardless of consequences.