<human>: Can you condense the text into three sentences or less?

we've been dating for ~6 months and things have been going really, really well so far. but the other day we had our first fight and I'm not sure if I am overreacting or if it's dump-worthy. 

I am also aware this may seem to be a juvenile issue to some, alas, I have feels.

the context: 

we got on the topic of past dating, and he starts to ask a question, "Am I the.. oh never mind" 

I press for him to finish the sentence for a bit, finally he does. 
"I was going to ask if I am the best looking person you've dated, but it's a dumb, silly and vain question so forget it." 

I realize he only didn't ask because he knew I'd ask him the same question, so I call him on it. He denies that a few times before following it up with this gold: 

"fine, she was really stupid though! you're so much cooler! you're awesome.. etc.. etc" 

I honestly can't even remember what else he said after that because I felt like I was suddenly slapped in the face. Basically, it made me feel pathetic that he hurt my feelings and then followed it up with compliments.

I ended up explaining to him that I didn't need him to put down someone else to make me feel better. That, in my opinion, relationships are about making someone feel great, feel the best and at this time, he is the most attractive guy to me. I feel I should be to him. 

So basically, I can't seem to let this go. I am worried it's a warning sign that he is insensitive, let it be unintentional or not. Or he may start making me feel insecure since that seems to be happening already. 

Am I overreacting for being so pissed? Thoughts. Thanks. I don't have enough female friends around right now, apparently.
<bot>: boyfriend said I was not the most attractive girl he has dated but then followed it up with reassurance. wondering if I am overreacting.