I am having troubles believing my boyfriend was joking around when he sent a few dirty messages to a female friend he has known for 4 years (where they have been only friends and no hook ups). We have all known each other for years and they were quite close prior to us getting together.
He was alone at his house and msging her kidding around about how all his friends like her butt.. Then he sent messages basically asking her what she was wearing and telling her to do things to herself and go to sleep. To his credit, He didn't include himself or tell her he wanted to do things to her or vise verser. He did write things like 'lol' and 'you know I'm kidding' throughout the messages. Also, through out their years of friendship, they would regular make such comments to each other and it was very normal in their friendship.
I found out through snooping which I hate that I got that low. Nevertheless, he apologized, saw that it hurt me and said he would never act that way again as he didn't think id be so hurt. But he swears that he was joking and feels I have made it into something its not. But he has totally acknowledged my feelings and really hasn't done it again. We still fight about it and it's been months and months since this happened. He always says "I can't tell you I meant those messages just to settle your doubts when I was joking like I used to". He even cries sometimes as he is sad that I have no faith or trust in what he says. He gets really frustrated with me but I feel like I have over-thought this whole situation and need advice from an outsider.
Would you believe it was a joke?

I don't know the guy so I can't say for sure but that seems like a little more than a simple joke or kidding around. I have numerous female friends and I don't say stuff like that to them. Also, he shouldn't really be saying things like that... did he not even consider you at all?

Look at it this way... What if you wrote those same kind of messages to a guy you knew. How would your boyfriend feel about that?

How did you find out about these messages?

Generally speaking when someone crosses the lines of good behavior;as I would say he has,it's time to rethink any relationship.

If you don't believe him after all this time, then you shouldn't even be with him. That's not fair. Let it go, or go yourself.