Originally Posted by Maritime Q-Scout
Alright, page 9 before I chime in. Bringing it back to post one.
But before I do. Been there, done that, got the t-shirt, unfortunately I didn't do it right. May you learn from my mistakes:
-Is it even possible to get out of this "Friend Zone" in this case? I figure maybe with a couple "real" dates she could eventually become attracted to me, but I am pretty much positive that she has no romantic interest in me at this point.
Contrary to popular belief it is possible, and I'm willing to be happens more than one would think. Of my close knit circle of friends, every single person in a relationship was best friends with their significant other first. In each case for years before getting together. It happens, and those relationships become some of the, if not the strongest relationships. However it doesn't happen quickly, or easily.
-How do I go about asking her out? Obviously I see it being a very awkward situation. Do I need to drop some hints about my feelings before I do this (i don't want to creep her out and just out of the blue, ask her out)? If so, how do I go about dropping these hints (since I flirt with her quite often and obviously its in a joking way, so she'll probably think I'm kidding around and won't take me seriously)?
Someone mentioned, turn up the flirt. They're right. You have to start slowly, an accidental bump while you're walking together, to brushing her arm when you laugh. Then gradually step it up to putting your arm around her for photos (while making a silly face of course, thus ruining the picture, necessitating a "good picture" with again your arm still around her), to being at the bar, saying come here I've got a secret but only you can know, and don't tell anyone. Then you put your arm around her, brush her hair behind her ear and say "I'm getting a beer, shhhhh", then promptly get a beer get back and say with a devilish smile "oh I'm sorry did you want a drink too?" Eventually make jokes about how bad she wants you, but you wouldn't want to ruin the friendship. Role reverse, joking put her in the position where you're jokingly rejecting her (even though she never asked anything) which will a) make her more comfortable with talking to you about a relationship, and b) get the idea of a relationship with you in her head - without you directly asking for it in the first place. Then, after time of course, make the gradual progression from friends to boy/girlfriends.
-Would our friendship be affected if i asked her out and she declined? Obviously with everyone its different, but in your experiences has the friendship been affected in any way? I wouldn't be heartbroken if she shot me down and would still see her as the same best friend, but would she feel the same way? She is easily embarrassed by awkward situations.
The answer is, unfortunately yes. At least at first. Over time you can get back to the best friend situation. Things wouldn't be exactly the same, sure there might be a big pink elephant in the corner, but as long as the two of you ignore it, it'll eventually go away. As stated above, I've been there, and done that . . . did it 100% incorrectly. But now, we're back to being friends, good friends, hell on a good day we're the best of friends. Sure she now engaged to a guy that's below her, but that's my perspective, and she's happy which in the end is what I wanted to see.
So: Turn up the flirt gradually, take it slow, line up your dominoes before watching them fall, and most importantly, have fun, be silly, and make her laugh.
Good luck, and if it doesn't work out, I have a friend that will help you cope, his name is Alexander Keith.
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