Very good friend of mine for two years, has been there for me in tough times and vice versa. We are both in university, although he is 8 years older. We started sleeping with one another 8 months ago occasionally. I've been very cool about it and tried not to get jealous, even when he told me about other girls, but I've had feelings for him since I first got to know him, and I need to tell him how I feel. He has a history of dating a lot of women, and the women he does settle down with are those that are emotionally abusive or play games, although he did stay with a girl for 6 years once (so it's not like he's incapable of settling down). He's a very strong personality and a bit of a difficult character, so I'm not sure how to go about it. I thought of saying something like this next time I see him:

"Okay, listen. You're a grown man, and you're an idiot if you don't know I have strong feelings for you.
Dude, look, you're a good friend, but if you did know I felt this way, which i'm pretty sure you do, then you've been using me, and this friendship.

I'm not okay with our dynamic anymore. I hate the way I feel when I get jealous or when I think of you with another girl. I think I was incredibly naive to think I could control my emotions.

So it's one of two options. The first one is obvious, we stop sleeping with each other, and we hang out less until I get over it.

Second option is to try exclusivity. I remember you saying once that the age difference matters to you. I think that's absolute bull. You're an intelligent man, it is beyond me if you think a number would matter. Age is just an indicator of emotional maturity. I don't think I'm any less emotionally mature than you. If you really want to be with someone, you'd date them no matter what age.

So, if you want to try, I'm all for it. I know it's a risk, but it's one I'm willing to take I think it could be fun, and I can meet you on every level relationship wise. If it doesn't work out, we can easily go back to being friends."

I wish I could give more details to give a more thorough picture of the situation, but I tried to keep it (relatively) short. It's killing me to feel this way. I can't concentrate on my education, my work, or anything. I would REALLY appreciate advice, especially if you've gone through any situation of unrequited love yourself.

Thanks in advance!

How old are you that you are both in university and he is 8 years older than you?
He is not using you or the friendship, he is doing what you have allpwed him do. If he is such a difficult character and sees a lot of women I don't know why you started sleeping with him in the first place, especially since you say you have had feelings for him for a while. I can't imagine your telling him you have srong feelings for him is going to make a difference, he obviously does not feel that way about you.
Don't give him any ultimatums, just stop having sex with him. Tell him you can no longer continue the friends with benefits relationship. If he cares enough to ask why, you can tell him you are looking for an exclusive relationship.

No, calling him a idoit in the first sentence is not the way to discuss it. If he loved you the same way he would not be talking with or being with other girls, you are it appears a booty call or a friend with benefitis. You accepted this and really should not be surprised he does not. Or he does know how you feel but does no care, since his needs are being satisfied.

It is time to tell him that you are wanting more out of the relationship, and how does he feel about it,

It is difficult to go from Friends With Benefits to a committed exclusive relationship, especially since he has many such relationships.

Its also even more difficult to just be friends after such an experience. You will always have hope he is ready to settle down with just you, and even if he does you will always wonder where he is, and who he is with.

You don't want to hear this but ending all contact with him and exploring your own world without him is the healthiest solution for you. Maybe it is best to hear this straight from his own mouth, but don't be fooled into even thinking you can go back to being JUST friends. It will eat you up and torture you until you hate yourself, or him.

Sorry, but its always difficult to change the nature of a relationship, and when one sex buddy gets feelings, generally the other doesn't feel the same.

How old are you that you are both in university and he is 8 years older than you?
He is not using you or the friendship, he is doing what you have allpwed him do. If he is such a difficult character and sees a lot of women I don't know why you started sleeping with him in the first place, especially since you say you have had feelings for him for a while. I can't imagine your telling him you have srong feelings for him is going to make a difference, he obviously does not feel that way about you.
Don't give him any ultimatums, just stop having sex with him. Tell him you can no longer continue the friends with benefits relationship. If he cares enough to ask why, you can tell him you are looking for an exclusive relationship.

Thank you everyone for your response!

Many things you said turned out right. I think that when I originally wrote my question, I was still upset and not thinking about the situation clearly. Thank you for giving me a better perspective.

I ended up talking to him yesterday. I was very calm, and very honest and with no sort of aggressive tone. Just told him how I feel.

The answer I got surprised me. First of all, he was a bit shocked to hear I felt this way. He also said that I am the person he is closest to recently, and he's afraid of losing that if he dates me. The age thing however, is completely meaningless to both of us, it turns out. His other concern is that he will probably move away soon, since he is looking for jobs in other towns too. If it were not for the job thing, the fact that we are very close friends would be an excellent basis for a long term relationship. He said he is definitely considering it but he needs a day to think. He did give me a hug, then made me food and we chatted like normal, played some music, watched a movie. Normal stuff. I think this is the best realistic response I could hope for, and we'll see how it goes from here!

In the meantime, stay out of his bed until he can make a commitment.