Search Results: ask her more than once

Me and my boyfriend were watching the circle, I commented on how I liked the girl's glasses to which he replied she looks like you but she's prettier. I was confused and shocked as I didn't comment on the girl's physical appearance, so I replied with "why would you say that?" He then said "what's wrong? it's just an observation" to which I replied : "I didn't ask for a comparison though I was complementing her glasses" he then was confused as to why I was bothered by the comment, and processed to tell me that if I told him someone was more handsome than he is, he wouldn't be upset and was like I don't know why you girls are so dramatic. To which I said any girl would be upset if her boyfriend out of the blue compared her to a girl and said they look similar but that she's not as pretty. Then he tried to cheer me up as he saw I was sad. I know there is a lot of people prettier than me, all of us have someone prettier than us, but I feel like he didn't have the need to say it out loud he could have kept it to himself, especially since he knows I'm insecure with my looks around him, we were friends before dating and he rated me a 6/10, once after having sex he said my boobs are a bit saggy and that I can workout to perk them up ( also without me asking and I never thought my boobs were saggy). Also I'm not his usual type as I know what kind of girls he likes. I've talked with him about all of this and he always reassures me that he finds me beautiful and cute which is hard to believe after hearing all his little comments about my looks and yesterday was the cherry.
Was I overreacting by being upset at his 'observation' ? Or were my feelings validated?