Looking for unbiased perspectives!

Trying to settle a debate, and would really like some input from an unbiased source. My bf (46m) and I (36f) were casually talking back and forth, when he makes the statement, “I almost went all summer without my favorite tea!” When I, (trying to be funny I guess .?) said, “yeah, but at least you didn't have to go all summer without your favorite me!” Then, I was like aww that was cute, commenting on the way it rhymed and how it was in general just dumb and cutesy. Whatevs. 

So he then tells me, “You're always cute, babe. Well.. usually.” The silence between us, becoming ever so awkward. He continues on. “Well, I could lie to you, you don't want me to lie to you do you? Because you know I'll tell you it's a lie every time I do.. Nobody's cute all the time…”

At this point I'm just like damn bro. Like why..? He now goes into this spiel about how I don't need to get all emotional about it, not everything needs to have emotions attached, etc. okay But, in regards to you, my boyfriend, of course I take things you say personally. We've talked about this type of thing before. 

At this point, i'm not trying to frame him as the bad guy, or as a jerk that said something crappy to intentionally hurt me, I know it wasn't said to hurt me intentionally. Ultimately, I'm just trying to understand why…? Like why continue on this way once you realize you said a thing and, I'm beginning to have some hurt feelings..? Why double down? Why was it even necessary to comment on whether or not I was cute or not? I didn't say or ask about his or anyone's opinion of the way I look. I said that my statement and the way it rhymed with his was cute. 

All this to say, we've found ourselves at an impasse. He doesn't understand why what he said could be hurtful, or why I took it personally to begin with. I, on the other hand, feel that I'm a pretty emotional person, and to me it makes perfect sense that I'd take his statements personally. We have a pretty personal relationship. Regardless of it eliciting an emotional response or not, I didn't react out of that response. I don't even hold what he said against him. But I also believe that I am allowed to have feelings; I don't act out, or lash out based off of them. Am I crazy? Probably. Am I too sensitive? Also likely. 

Would love to hear some other perspectives.