| i think one of the hardest transitions to make in any relationship is that from a strictly platonic friendship to an intimate pairing. it can be so tough to break down the limits you've established over the course of time, and the longer you've adhered to those boundaries (i.e. not making a move on your friend), the more enforced they become, thus making them exponentially harder to break down.
so what's the play here? if and when you decide you want to take things to the next level, for whatever reason, what's your move?
the reason i bring this up is because i'm honestly stumped and i need your guys' advice. i don't pretend to be a master PUA, but i like to think i have a decent understanding of the game, and this one's got me.
here's the background:
i've been great friends with this HB, call her jen, for several years. we met during high school where we floated in the same circle and hung out quite often in open social settings.
we've gotten progressively closer over the years and are now very comfortable around one another and each other's friends. i'm tight with her family, and she is with mine, i even attended a wedding her cousin's wedding as her date this summer, and she's come out to visit me at school (i go to school in california and she's in illinois where we're both from).
the reason things never got any farther is because we've been overlappingly in other serious relationships. she's been with the same boyfriend for 4 years off and on and i've been in and out of a serious 2 year relationship. we've hooked up twice, both times really drunk and when she was separated from her bf, and we've never spoken about it.
she broke up with said douche bag boyfriend (who was and still kind of is borderline emotionally abusive) about 4 months ago and we've been hanging out pretty frequently.
tonight a buddy of mine was having a house warming party in downtown chicago at his new apartment. she called, asking what i was up to for the evening, so i invited her along and we made our way over to my friend's place where he and some other guests were having a great time. we drank, danced, talked, laughed, flirted, everything we normally do as friends. at the end of the night i drove her home, gave her a kiss goodnight, and turned in.
there's a boundary here, one if crossed could end whatever we have. this is far different from any pick-up i've been exposed to. there are rules that have been established, trust issues going on, and i don't know what the right move is.
i want to take this relationship to the next level, but don't want to ruin it with any grand gesture of affection, or let any kind of spark fizzle back to being in the friend zone.
what's the right play?
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