I've been through some questionable relationships where I can kind of see a trend of what are red flags. But at this point I'm not sure if I'm just bugging...

So already in a bad spot, we work with each other but we both work with a contract for our job. It ends in 6 months and we've been dating for 5 already.

There are just some parts where I feel chest pain (yall know what I'm talking about when they unintentionally hurt you ig?). I've always openly communicated with him what I've been through in the past and what bothers me and he listens and is very understanding. I always have these questions that I ask randomly bc it just pops up. Like " will you still love me even if I gain weight and look different?" And his response was that he won't be happy with me but he'll still love me....what am I suppose to say to that? It's like a backhanded answer? That and he makes jokes that makes me uncomfortable like comparing me to a dog...am I just focusing on the negatives? Am I being sensitive? Do you think if I talk to him about this, he'll stop?