Hi Jane,

I'd say that you and Bob haven't quite 'bonded' yet emotionally that's why you're considering John.

Unfortunately, you can't be sure if it's going to work out or not with John (the way you don't know for sure if it's going to work out w/ Bob or not).

You have to make that decision if you want to make that jump or not if/when he decides to go ahead and ask you out. If it doesn't work out, then it doesn't work out and you may have to make that hard decision to really 'move on' by distancing each other (because once you break up and you're still close, you're still pulling toward each other and will be in 'relationship' limbo/hell).

I had similar experience w/ you. I was dating other men when my best guy friend John decided to ask me out on a date (he emphasized that it was a date not just our usual friendly outings). I was mildly surprised (well, not really, because he hinted around), and after careful consideration, I said 'Ok.' So we dated and he asked me to be his serious gf, which I agreed to. It was actually one of the 'best' relationship I've had, unfortunately, in the end it didn't work out. So we broke up.

And again, sadly enough, I know that both of us needed the space to 'recover' so we had to distance ourselves from each other. But it's all good though. I mean, I'm still friends w/ him now (we're both married to different people), but it's VERY different friendship because we've both had our best friends already (in our spouses).

Good luck to you.

*Unconditional love is a beautiful thing, just be sure to give it AFTER your conditions have been met.*

If you had romantic feelings toward your friend, you'd know it by now. Don't ruin a friendship out of curiosity.

I'm going to go with luisamapacha...i mean what "if" it doesnt work out?? then you will begin to feel awkward around your best friend. I dont want to be cynical here but, I sincerely dont think its worth it. Obviously you are hesitant for a reason...because you know it could lead to disaster then all the years of friendship is down the drain. Consider the pros and cons but from what you are saying..."curiosity kills the cat".

Make a pact that if you're both not married by 40 you'll marry each other. Then he has a hope in the future and you can feel free to do what you want. If you two are meant to be, you'll be. You're too young to f*ck up a friendship that great for something you're not 100% sure of.

"Don't fall for someone who's not willing to catch you"

GO FOR IT!! My current fiance and I met when I was 14 and he was 16.. and he was also my best friends boyfriend.. Which opened the door to a friendship.. He begged and pleaded for us to date for years after he and my friend broke up.. I wasn't ready.. Then I did my share of begging.. He wasn't ready.. But then the right time must have rolled along. 2 1/2 years ago we became a couple and in two years I will have his last name. Through being best friends it brought us ridiculously close. Now.. we are still amazing friends but we share so much more together besides friendship. I say it is totally worth it. I never imagined my life with anyone else.. even from the minute I met him. I knew it. But I also knew it was going to take a while. I believe you should go for it. You don't want to leave this stone unturned. Your friendship will be able to take on a new angle of your relationship and grow from it. If it doesn't work out.. It's OK!! But at least give yourself a chance to be with a man that knows you already and after all this time thinks you're his perfect match. Don't hesistate on this!!

I think it's worth risking the friendship. Always.

I actually think you already answered your question.

"I feel completely unsure about this. "

"I have never thought of John as anything other than a friend" - Obviously you are not attracted to him, which is going to be a problem...

"I have never gotten along or connected with anyone like I do John. " - because he is your FRIEND.

I think you should just take it slow and see if your feeling changes since he confessed. You never know, 2 yrs from now you guys might be getting married...

I agree that love is always worth risking a friendship for. But if in all the years that you've known him, you've never felt attracted to him once .. then that would be a different story. I can't tell from what you wrote whether you've ever felt this way or not .. I'd say take a chance on him .. Maybe go out on a few dates and see where things go from there.

The bond you have with a friend is very different than you have with a significant other. so what if you both have the same taste in movies, there are much higher priorities when it comes to a relationship.

I, too, dated my best friend who only told me he had feelings for me once he realized he had competition. We actually dated for four years then grew apart. Not because our personal preferences changed, but because he wanted to raise kids differently than I did. He had different core values than I do. That serious type of stuff. And you know what? He doesn't talk to me anymore. We are not friends at all.

I say trust your instincts. If you do not have romantic feelings for him, I see no reason to go along with what he wants. If however, you do have romantic feelings, then go for it.