A
male
age
36-40,
*rawfish1
writes:So I find myself in the same situation I have been in once before. I have a female best friend, actually my REAL best friend. Years ago I found myself starting to have feelings for you, now mind you this was in high school we were very young. Years later we are still close if not closer and in our 20's. We have had a couple small falling outs within the years but still found eachother again, lately we have been spending alot of time together having fun!! We both have been through some rough relationships, her especially and I've always been that one guy thats always been the shoulder for her. I find myself years later falling in love with her, for the right reasons too. We flirt alot, have joked about hooking up and even always joking about getting married some day. We have brought up dating a couple times but didn't really get into the subject, just she was in a bad relationship and I was dealing with a break up and also talking to someone else, she has even told me we should have just dated. I somewhat have hinted to her how I feel but still keeping it cool because years ago it was the friendship she didn't want to ruin. My thing is we are older and more mature, and I do truly feel we could handle dating. I want to tell her how I feel with hopes she may feel the same, especially with the flirting and all the joking around we do about dating and getting married. Like I honestly WANT to marry her. Any advice?? Thank You!!
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a break, best friend, flirt Reply to this Question
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male
reader, crawfish1 +, writes (4 August 2010):
crawfish1 is verified as being by the original poster of the questionThank you for the feedback I really appreciate it!! Maybe I am just being scared and shy because we have been down this road before in high school when I had feelings and she didn't have them, but people do change and things change. You are all right, I really just need to go for it. Thank You!
A
female
reader, M€9@/\/ +, writes (4 August 2010):
Well I am best friends with this guy I have known for a while. We never joke around with going out but I know he likes me... A lot. But I know that it would complicate our relationship if we did end up going out!
you did say that you have joked around with her right? Tell her how you feel.. Who knows she may feel the same as you but might be too shy to bring it up?
My philosophy: be like Nike and "just do it"
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A
female
reader, tennisstar88 +, writes (4 August 2010):
 Ur the guy in the movies I love!!! Didnt u learn anything from those movies? Sometimes your male best friend does make the best husband.. I would ease the dating topic into discussion spill it tell her how u really feel...omit the marriage part for now because telling her u want a relationship is a lot to digest at first. Whats the worst she could say? No and you guys go through an awkward moment in ur friendship that can be turned around due to the fact that u guys have been friends forever..Or she could have the same feelings pent up and it could blossom into a beautiful relationship..either way u gotta take a risk!
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