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Challenge: going on a "date" with a long time friend


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Posted

Ok i tend to write novels ill try to keep it short.

 

I met this girl 13 years ago when i met my now ex fiancee. She was her best friend. They have drifted apart, no blowout or anything although their relationship did get rocky at times. This girl was going to be maid of honor at our wedding which of course never hapoened. My ex fiancee has now moved to NZ and is married, this girl was not maid of honor his time, due to distance, growing apart, i have no idea i didnt ask.

 

My ex fiancee always thought there was something going on between me and this girl. Never was. We had a few moments there where i just wanted to kiss her so bad but i never made a move because she was my fiancees best friend, and duh, with her sleeping in the next room if she got up to go to the bathroom it would be ugly. She would come over to see my fiancee, she would be lame and go to bed super early, me and this girl would hang out drinking and talking until the sun came up sometimes. Once i fell asleep on the couch with her with my head in her lap, woke up in a bit of a panic and snuck back into bed before my fiancee woke up. We kept our mouths shut about that one because it was an accident, nothing happened at all, but my ex fiancee would have freaked. Of course, given that i later caught her having an affair.

 

Well since breaking up with the fiancee ive ripped through 4 girlfriends in 6 years. This girl had met someone shortly before i broke up with my fiancee. All of my girlfriends since thought that either something was going on, or when we broke up they all told me i should get with this girl. My most recent ex is annoyed at the girls im seeing mostly because she thinks me and this girl are made for eachother. Ive only ever seen her as a friend, but there have been sparks from time to time.

 

Well, given that this girl is single and so am i i wanted to hook up with her and just hang out, sans me a girlfriend scowling in the background and ditto for her boyfriend (her boyfriends seemed to scowl like my girlfriends but i never heard any reason why).

 

Were going out to a dinner then some dancing. She was going to go with her ex (its a one time lobster thing) but when i said id go she ditched him in a hearbeat. I let slip that i was her date for the night, she questioned it, and i nust said, no, were both single, dinner and dancing, im your date. She didnt get offended or anything.

 

I have a girl that im right close to making my girlfriend. But before it becomes real i just have to go out with this girl as a single guy, and her as a single girl, and just see what happens.

 

I dont want to sit there hitting on her because shes my friend, but i want to leave the door open too. Ive known her for 13 years so i dont want to burn any bridges. Im staying at her house probably in her room as she has roomies but she has both a couch and a bed in there.

 

Im not been secretly holding a crush or anything, but i keep hearing from ex girlfriends (and even my fiancee when we were still together) that this is the girl i should be with and i want to see if it.falls into place. Whether its a hot forbidden one night stand, a real romance, or just a kiss that reveals that it was never meant to be.

 

If i get into another relationship which i probably will soon, i want to know either way.

 

Any advice from the ladies as to how to make sure she both knows that im open to crossing the friendzone divide but without coming at her? Were probably going to be drinking a lot which will help loosen things up. She broke up with her ex long enough ago that shes starting to put herself back on the market but nothing solid yet. The timing is impeccable. Ive dated my ass off since breaking up with my ex so no worries of rebounding.

 

Advice?

Posted

just be up-front and get it out there like it might be your only chance to tell her. tell her how you feel the last 13 years have brought you to this point/place and you think there might be something worth exploring with her if she is open to that. and leave out the part about how you might be getting into a relationship soon with someone else, lol

Posted

Don't make it too heavy. Just tell her straight 'I've always enjoyed your company, but for a while now I've been wondering what it'd be like to date each other. Would you like to go for dinner on Thursday?'

 

It really shouldn't be that big a deal if she says no. But you convey your interest clearly enough that the intention is clear.

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Posted

Were already going out for dinner and dancing. She lives out of town so im staying the weekend (at least the night) at her place.

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