In my experience this is a mistake many, not just men, people new to relationships tend to commit. It is a pain-game in which you tear at the other persons emotions in order to see them more clearly. A game that can become very addictive.
It would typically stem from an insecurity of your feelings towards him. Doing what he did forces them to the surface in an intensified manner. Now I am naturally only guessing and for all we know he might just have the world's worst humor, but this is the explanation that seemed most relevant to me.
Stopping this game is typically about making doubly clear that you won't tolerate it but that you do, really, truly love him. And remind him of that, a few times more often than you would normally think necessary.
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He is testing your reactions. It's a form of manipulation.
"my boyfriend and I had kind of a big conversation about me needing to work on things"
Seems like HE is the one who needs to work on things. Who the fuck does something like that, and *twice*? Honestly, the second time I would have enough and just be like "fuck yeah we are, I don't have time for this crap anymore".
Seems like he's just testing you, especially since he wanted to see if you cried. It's like a fucked up way of seeing how much he matters to you and how you'd react if you broke up for real. That's really childish and pathetic. You should really ask yourself if this is the kind of person you can trust and see a future with. You don't play around with serious shit like breaking up. So insensitive.
My boyfriend has done that too and asks me if i cried like wtf is going in their minds, then he would say i was testing you but you were so ready to break up that you didn't even ask why or anything, the last time he did that i cut everything with him until he begging to see me...
This... Sounds rather harsh and insensitive of him... I really do not see why he'd do that to you? You should tell him to stop joking in that way, I'd get hurt and become insecure if my partner did these things as a 'joke'.
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That's a very strange behavior on his part.
To see how you would react
he's a joker.
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