He jokes about breaking up. does that mean he's thinking about it?

Anonymous
Me and my boyfriend have a great relationship. I do have my own emotional problems from having a pretty rough life, but I'm working on not being guarded from it. Despite that, we're very emotionally connected, we play and joke, don't have fights, and we spend a good amount of time together. He wants us to move in together in a couple months and mentions getting married. But sometimes he jokes about breaking up, like me leaving him for someone else or last night he said, "if we broke up and stayed friends, I'd be disappointed to learn if you ended up dating any of your roommates since they're doing nothing with their lives." One of my roommates is really attracted to me so I'm sure he's aiming towards that guy. But still, that's an oddly specific thing to say...

Should this concern me? Should I bring it up to him?
He jokes about breaking up. does that mean he's thinking about it?
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