Is it a good idea to hook up with someone you've been friends with forever?
919264
Don't make the same mistake twice.  There is a reason you have been friends for so long.  Do it and take the chance.  You have to think about it this way....You take chances with total strangers all the time without knowing them at all.  Why not give the same chance to someone you know you already LOVE!!!
1091591
Every girl you'll ever meet has a past. How can you get around that? If you didnt know this about your GF and BF before, how is that possible? And that leads to other questions you have to answer to - (for yourself, thanks)\n1. how does it really, (really) matter to you that they - if they did - had sex earlier in life?\n2. whom is the most important for you of the two? whom do you want to have a future relationship to?\n\nIf you care for her - you stay with her and keep the friendship with your friend.
607586
well a friend is a friend i think they should be friends no matter what i mean dont let 1 guy come and  end a friendship a booty call is not worth the friendship and that is the only thing he wanted so never end something good over something dumb
248732
I'm assuming you are good friends since you've known each other for so long but I wouldn't want you to scare him off either.  I would just kinda drop hints and see how he takes it and when the time is right to tell him then you will know.
563247
Oh just go for it - it's a cute idea, provided he isn't married.  Then if you end up with him, years from now you'll have a special shared memory to tell your grandkids.
391888
do u really know him that well bcuz if ur friends then u could get a couple of ur friends and his friends and get together at someones house \n\na little bonding with his friends never hurts:)who knows maybe you'll end up hooking up with one of his friends
528054
His problem might be the way that you refer to this long time male friend in terms of endearment... as someone who has been there for you through the good, the bad, the ugly, etc. \nNobody wants to hear that, and it's not going to boost his self confidence or trust by being compared to your other male friend. \n\nI'm wondering why you're going out with him, instead of the friend who has given you much already?\nIf you're not attracted to your friend, then you should decide who you want to be with, and who's going to be there for you when YOU need him. \nOtherwise you're going to keep on hurting the man you're with, \nby wanting to keep your options open when you feel the need to find alternative support from another guy.
1101857
you're both consenting adults, and as long as you're both hot for each other, go for it! and if other people don't like it, too bad, you gotta live your life for you. \nand if this is from someone who is a friend or family member of either the 50 year old woman, or the 25 year old guy, that is the person they chose to be with, leave them alone. it might be just a fling, or it may be a deep meaningful relationship, either way only time will tell, and if they have found a happiness with each other, no matter how long that time period may be, let them be happy. happiness is a rare thing these days.\ngood luck to you
37945
If she is a friend, a good friend, she should understand your motive and respect your honesty.Who know maybe somewhere down the road you two probably can hook up and see if there are any sparks for each other.If she is a friend she should understand.
600681
If you guys still have a friendship then go for it. Just hang out with him and see what happens, that is what I plan on doing with mine too.
700046
It will possibly ruin your friendship and if you are dating someone you should not even be considering it. If you do there will be conseqences. I suggest that you don't do it, it's not worth loosing a friendship over.
682650
Absolutely!  Don't risk it if you have a good friendship.  The friendship ending will hurt more than the relationship.
323214
NEVER ever NEVER miss a chance to meet someone new, even if just to be friends there was obviously some chemistry being you both saw eachother more than once and were both too uncertain to make the first move, sometimes being a little more aggressive can pay off, just imagine if you would have just said hello and introduced yourself, you could have possibly at worst have a great new friend to hang with.. my personal advice for the future is you only live once and make the best of every experience you have in your life no matter what it is!! Good luck on your next chance at Mr So Hot!
753283
If you trust him yes just be careful, don't be nosy but if they want to hang out make sure he invites you.  You and hopefully he wouldn't want to loose 8 years over a old fling.
296583
This idea sounds good, but never actually works out. Unless it's a one night stand with someone you know you're never going to see again. Other than that, there is always going to be some emotion involved. Even if the other person agrees to just being sex buddies, they're probably just doing it to keep you aroung because they'd rather have you that way then no way at all.
841400
Yes you can it comes down to do you trust her enough.  I am still friends with a guy i dated for 3 years and there is nothing sexual at all between us but we love to talk still.
829819
Yes. It is possible. I have been friends witha guy for years...nothing's changed...we're just good buddies...