Recently I just slept with one of my closest guy friends. We have known each other for over 6 years and went to the same high school and ended up going to the same university. I have always been a guys’ girl, and for the most part everyone saw me as one of the guys. As a group we would go out together mostly to go and play some sort sport. It didn’t really matter whether it was hockey, soccer, basketball, martial arts or football. They treated me and roughed me up just like one of the guys.

However there was one friend in particular who I was close with in the group, let’s call him “Fred”. During high school I dated one of the guys in the group name “Rob” (who was my high school sweetheart). Things didn’t work out, but me and “Rob” stayed friends. My friend “Fred” who was from the same group of friend, had been always there to offer support and was someone I could talk to about life, men, school. And I offered the same service for him.

When we started university we became flirtier and our conversations began to include more intimate topics about our relationships. The whole time I have known him I have had a few boyfriends and he has had his fair share of women. Two years ago, I had a particular bad break-up, and dependable “Fred” was there to offer a shoulder to cry on.

Jokingly in a conversation I brought up we should be friends-with-benefits; at least we wouldn’t have to deal with the headache of relationships. We laughed it off and never acted on it. At the time “Fred” had been trying to date another, so I backed off on our friendship as not complicate things.

“Fred” never ended up dating the girl and came back around. He wanted to re-explore the friends-with-benefits option. But at the time I had started dating a new guy, so he backed off our friendship as not to complicate things.

For the next 2 yrs, we run into each other at school and with friends. We talk, we workout, we playfight, insult each other as if nothing had changed, from time to time he’d bring up being friends-with-benefits but would tell him I couldn’t because I was with “Mr.X”. However my relationship with “Mr. X” with fighting (physical & verbal), resentment, insecurities etc… and there was “Fred” to hear all my complaints again.

After 2 yrs “Mr. X” and I broke up. I needed a change, I wanted to feel happy. So “Fred” and I decided what time than now, he picked me up after school and we went back to his place. We had sex. And it was great. After we went to play basketball with the other guys and played it off as if nothing went on.

We’ve talked about the incident, just to make sure we were "OK". And since then I’ve gotten back with “Mr.X” to give him one more chance to change. “Fred” and I are still friends, maybe closer now because of everything. Before getting back with “Mr. X” I told him about the day with “Fred”, he was very upset but still wanted to work things out. There’s no way I’m willing to give up my friendship with “Fred” because of “Mr.X”s and his insecurities. We fight about it often and it makes me less willing to work things out. I just want to be happy and not feel trapped like before...

:confused:
What should I do?
I think I might be catching feelings for my friend…
Do you think it’s mutual?
Or Am I only feeling this way because my relationships have been failures?

Thanks for reading (I know it’s a long entry)
Hope to hear people’s input

I think that you should make a list of pros and cons for each guy... and there have to be some feelings there if you slept together and afterwards stayed around just ask him if he is catching feelings too sometimes friends can be the best lovers and mates

Mr. X has every right to be insecure, some things are better kept hush. You bumped ulgy w/ one of your best friends and you think Mr. X should be cool with it. Talk Fred and see where you two stand at this point then decide to pursue a relationship or stay as friends. As for Mr.X I think the 2nd chance is doomed because he won't get passed the "sex w/ bestfriend while we were apart story."

So many things to consider here:

First of all, why would you got back with Mr. X. You broke up for a reason. And... if you were going to give him another chance, why would you tell him about Fred? How would you expect Mr. X to react? I'm surprised that he's still willing to give you another chance. Think about it from his perspective. You guys broke up, you had sex with another guy and now you want him back? If I were him, I would think... when's this girl going to break up with me again and have sex with some other guy again. There's no reason to go back with Mr. X. The trust is really shaken.

Secondly, if you are confused about your feelings for Fred, then you should not be with Mr. X. You should be single right now and spending time trying to sort out your feelings. Right now, you are leading both guys on. Both guys are putting their lives on hold to see what decision you want to make.

Thirdly, there's nothing wrong with what you did the in the past. There was nothing wrong with having sex with Fred, you were both single. It's good that you guy backed off each other when you were dating other people. At least you guys did not cheat on your significant other. But right now you are borderline cheating. Some may say that you are emotionallly cheating because you might have feelings for Fred and you're still dating Mr. X.

Break it off with Mr. X. Sort out your feelings before you commit to one guy.

Why not just be single, and explore your world, and find your own happiness on your own?

That has to be better than the drama, and confusion you're in now, and with so many mixed feelings, the last thing you need is a relationship.

Figure your own feelings out first, without any outside influence. Then you can make a better decision for yourself.

First off, I'd like to thank everyone for their responses

When "Mr. X" and I broke up, it was I who took him back
I wasn't sure whether I wanted to work things out & whether it was worth it. The only reason I told him is to give him more information to determine whether it was worth it for him. We only got back together because he was "OK" and accepted everything. But now he refuses to hang out w/ my boys (b/c there's a chance "Fred" will be there)

As for "Fred" we're friends. He says he sees me as the same. And I've told him I feel the same way except now I know how he looks like naked. But our conversations have made a farce out of the situation.

Sometimes me and "Mr.X" fight and he insist that I should be with "Fred"
I think he says that because "Fred" has more to offer on paper (university, work, sports etc... )
While "Mr.X" has been unmotivated, hates being active and has dropped out of college and only works part-time

"Mr.X" has always been intimidated by my friends because a lot of them are althetic or kickboxers. His jealousy as been an obstacle to overcome these 2yrs
Our relationship is based on the condition I keep my friends because previously I had to cut them out of my life

As for feelings, it's a mixture of influences
- I could be unhappy w/ "Mr.X" and secretly have given up all hope to work things out
- I might want to pursue something w/ "Fred" because he has been the only guys not to cause me heartache
- I'm bored and feel trapped being in a relationship in general
- I'm afraid on commitment because I don't want to get married

And the list goes on

Some of my guy friends including "Fred" want me drop "Mr.X" and get back together with "Rob". This adds more confusion about the whole situation :confused:

As for being single...

It would be difficult because hanging out w/ the guys and "Fred" would be a constant reminder of how complicated things are... :confused:

"Mr.X" and I tried to be just friends but he admitted he would always be trying to win me back.

Sometimes I just want to wait and let things blow up in my face :eek:

Your confusion comes from to many people pulling you in the directions they want, and to be unconfused, you must decide what you want.