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Hey there,
I have a neighbor that I find attractive. We've hung out about like 5 times. (She's asked me to hang out 2 of the times). I feel like each time we hang out we get a better understanding of each other and its been smooth each time. I'm having trouble escalating with her for some reason. I don't know if its the fact that she lives right underneath me or if she doesn't feel that way towards me. Any tips on escalating with her?
I can see no one has really helped you so far so here's my advice.
Start off with judging her interest level by body clues; although you probably don't have to do this because if you've hung out 5 times she clearly likes you.
You could also try testing her body responses based on your body movements/positions to see if she mirrors your actions. Face your feet towards her when you're talking and see what she does. Act like you're grabbing something and then sit down back next to her but this time sit a little closer and be slightly touching her. See if she readjusts herself to stop your legs from touching (bad sign) or if she doesn't move it means she's okay with it (good sign).
From there you can try a number of different things. If she has holes in her jeans then put your finger in one of them playfully and say something like "hey did you know you have holes in your pants?" or "wow you're pants must be pretty religious, look how holy they are."
The last thing to do is have a good conversation, let the conversation die down/taper off, and just look into her eyes and her lips. If she maintains eye contact for 3 seconds she probably wants you to kiss her. Human beings don't like awkward silence while staring into each others eyes so if she holds contact then just go for it.
If/when you get to this moment remember this line I'm about to tell you: "Just. Fucking. Kiss. Her. You. Pansy."
You'll be less sorry for yourself if you try than you will be for not trying at all.