best friend to more?

[darkhawk79]

This is complicated, so bear with me.

 

First, some back story:

 

I and my two best friends are 33. I've been friends with "Joe" since I was 7. I've been friends with "Jane" since i was 17. Joe and Jane have dated on and off since we were 17.

 

Jane and I dated for a few months around the end of high school and we broke up when I went to college. As I said, since then Jane and Joe have continued to be on and off, until a few months ago. He didn't love her the way she wanted (and in reality loves someone else). It was essentially a comfortable hookup for him, and nothing more.

 

Though I continued to date other girls (even her friends), I harbored a crush on Jane. Eventually I moved back home and told her. She told me that she loved Joe, and that was it. There was no weirdness (seriously), and eventually I got over it.

 

Fast forward to the present:

 

I've dated multiple girls in the ensuing years. After years of everyone (myself included) telling Jane that she deserved better, she eventually broke it off and started dating again, albeit unsuccessfully. I broke up with a longtime girlfriend a few months before.

 

Here's the thing:

 

Jane and I spend a lot of time together and always have, even when she was dating Joe. We go to concerts, have dinner and go on long road trips etc... alone together. We flirt easily and constantly. We have always been each other's surrogate bf/gf (without sexual intimacy) when needed. I was her date to her sister's wedding and our families love each of us almost as their own. Our families and closest friends, waiters, bartenders, strangers, and even my recent ex wondered if we were together...and if not, why not?

 

Lately I've started to wonder "why not?" myself. We know each other like no one else, we've been sexually intimate before (albeit a long time ago), and there have been times recently when I've felt an overwhelming urge to kiss her out of nowhere. I'm not sure if it was my breakup or hers that has caused some feelings to come back...or if it is actual romantic feeling coming back for some reason. I'm thinking about explaining this to her in the near future. Possibly even suggesting that we try dating again. Or just plain kissing her.

 

So...any suggestions?