You have to be honest with him. As his former BFF, you owe it to him to be straight-up and say it just isn't working for you. It's not fair to him to be with someone whose heart isn't in it. He's a great guy, but deserves better. It's a cliche, but the old "I appreciate our friendship too much to jeopardize it" never fails. Sure, it may not be fun for him to hear, but it's always true. Your friendship is more important than a relationship that your heart isn't into.
In the end, it's hard to argue with "I just don't feel as strongly as you do. You deserve better." Sure, he may say he's okay with being with you if your heart isn't 100% into it, but in his heart of hearts he doesn't really want that. Once you say those four painful words ("we should be friends") the fight is basically over. You may never actually be friends (that's up to him), but at least you will have been honest and let him down in the nicest way possible.
Plus, if he's really a writer he could use some heartache to toughen him up. Who knows, maybe you'll inspire him to write the next great American novel. Or at least a crummy zombie romance screenplay that he can sell for a million bucks.
In the end, it's hard to argue with "I just don't feel as strongly as you do. You deserve better." Sure, he may say he's okay with being with you if your heart isn't 100% into it, but in his heart of hearts he doesn't really want that. Once you say those four painful words ("we should be friends") the fight is basically over. You may never actually be friends (that's up to him), but at least you will have been honest and let him down in the nicest way possible.
Plus, if he's really a writer he could use some heartache to toughen him up. Who knows, maybe you'll inspire him to write the next great American novel. Or at least a crummy zombie romance screenplay that he can sell for a million bucks.
Thank you so much GC! only problem is hes SUPER bummed about his two friends moving away and the fact that he's unemployed. I tried talking to him about it and he said he was at his lowest point and was in tears saying hes not ready to give up on us. Eep! How do I tread lightly on this???
eesh that stinks. but it could be that he's not ready to give up on you guys because he has other bad things going on, and you are the one good thing that is sort of keeping him happy. but that's not your responsibility, even as his BFF. the only person that can drag him out of his lowest point is himself. if it gets too overwhelming you may not be able to tread lightly and may have to just tell him like it is. but tell him he's stronger than he thinks he is, and that no matter what you will always be there for him, for supporting but not for smushing. and then maybe step back for a little bit and let him figure it out on his own, he will. you can still be a support and stay in the background of his life, without being his girlfriend. right now it sounds like you are putting his needs before yours, and from the limited information it sort of sounds like he is guilting you into that. what he is doing isn't fair in my opinion. it's hard to tread lightly when someone rebuts a breakup, stick to your guns tho because you have needs too. as a BFF, he has a responsibility to honour your needs as well, good luck!
If he can't take a hint, then you're gonna have to be blunt and direct. He's gotta accept that you aren't into him. I'm assuming he's been cool enough to earn his place as your BFF. Well, part of being a friend period is respecting your boundaries. Make it clear, direct, no sidestepping, no indirect words, no euphemisms, that you aren't interested in a relationship beyond friendship. I'm sorry he's going through a difficult period, and its great you want to be there for him. Nonetheless, circumstances are not an excuse to disrespect another person's boundaries.
If he refuses to honor that, then you will need to reconsider your friendship with him.
AGH HELP AGAIN HE JUST PUT FLOWERS AND A MIXED CD IN MY MAILBOX. SERIOUSLY GUYS. GAH.
Why do they make it so hard?
Not all of us do, Lilly. Whenever a woman told me "not interested", which was very often, I always said "OK" and moved on.
Did you recently tell him, in no uncertain terms, "no"? If you hadn't yet, please, do so. If he continues to court you, he's failing to respect your boundaries, which is disrespect to you as a person.
Give him one last chance, sit him down, explain to him, you very value the friendship, but you don't have any desire or intentions of being anything more than a friend, and you need him to stop with the moves, because they will jeopardize the friendship if he continues.
If that gets him to stop, then all is good. Otherwise, and I don't say this lightly, you need to break off the friendship.