My boyfriend and I have been together for about two years. We're best friends, and honestly, our relationship is wonderful. It's just so much fun, based on a foundation of mutual love and respect. It's the kind of thing that gives you that warm, fuzzy feeling at the same time it makes your head spin and your heart race.
We're very open with each other. Neither of us have a problem with telling the other that we find another person attractive. I mean, he knows about every single guy I've ever had a crush on, and I don't ever think twice about saying, "Oh, he's hot" about some random guy in front of my boyfriend. Likewise, I know all about who he's liked and his "type" and I could rattle off a list of celebrities that he finds attractive. I don't have the slightest problem with that, on the contrary, I like that he knows he can tell me anything, even when it's something like that.
The only thing is... Sometimes, he takes it a bit far. I mean, he'll say something like, "Man, she's so hot, I could just... mmmmm." and he won't just let it go at that, either. He'll go on and on about some random girl, and he does it just to upset me. Oh no, I kid you not. He admits to this. Sometimes, he doesn't even find the girl all that attractive, and even when he does, he's like me, he wouldn't do anything with anyone without knowing them really, really well first. He just likes to upset me. I'm not a very jealous person, but it makes him feel good when I get jealous, so he provokes me.
Now, let me say that I do kind of understand this. His self esteem was really low before we met, and I think that part of this is just a remnant of that. He needs the assurance that's provided when he gets a rise out of me. I love him very much, and I don't ever want him to, even for a second, have to wonder whether or not he's totally and completely loved and accepted, so I'm constantly showering him with love and praise, and while he obviously likes it and is reassured by it, that doesn't seem to make him feel as secure as the knowledge that I want him badly enough to fight to keep him.
We have talked about this, and he acknowledges and agrees with everything I've said and feels bad about it. He tries to change, but when he does that, he becomes almost lifeless. It's like he's trying so hard not to say anything that will hurt me, that he doesn't say anything at all. Obviously, this isn't at all what I want. I still want him to tell me all the things he tells me now, but without being intentionally hurtful about it. ("Oh, she's hot" is fine. "Oh, she's hot. What I wouldn't give to...." is said with the intention of getting a rise out of me.)
I don't want to give the impression that he's a jerk, because he really isn't. This is the only cause I've ever had to complain about the way he treats me. Except for this thing he does, he is the sweetest, most caring, most loving, most respectful guy I've ever met. (Even my parents love him!) Just to give an example of the other side of him, the last thing he said to me before we got off the phone last night was, "I love you. You remember that, okay? And everytime you look in the mirror, remember that you're the most beautiful girl in the world, because that's what I think everytime I look at you. I love you so much, sweetheart." in that adorable trying-not-to-cry voice that guys sometimes do. (Ladies, you know what I'm talking about, right? ;o) )
So. I'm not exactly sure what I want advice about. I've already decided that if I need to, I can live with this, but I'd rather not. I know this isn't something that would cause me to break up with him, but I want to built a healthy, lasting relationship, and I want to know how I should treat this. Should I just continue putting up with it? Should I tell him to stop, and live with his lifeless, robotic attitude after that? Or is there some way that I can give him all the love and reassurance that he needs without him provoking my jealousy?
I'm sorry this is so long. :o/ Any advice at all would be really, really appreciated.