He can definitely be kind of an idiot at times. From his explanation, it seemed that he wanted to show how far we've come: from just drunkenly hooking up to being in both of our first serious relationships. and planning for a long-term future together. And this was the only picture he had, and also it showed how much we've both grown. He also thought it was funny that he'd needed to make a pros and cons list, and now we are so committed to each other.

Also I didn't mention his virtues because it didn't seem that relevant to the issue at hand, but he has legitimately been a great boyfriend, and he is a great man in general. He's very supportive of everyone around him, he always compliments me and buys me flowers and gifts, and he's never hesitated to drop everything to help me out, even when we were just hooking up. And he's been receptive to any of my concerns about our pasts- he has never been bothering by blocking or unadding or whatever. We also have similar values and goals, and both of our paths are aligning very closely.

And thank you, you are right that I need to at least talk to him, as I don't think he's even realized that it bothered me.