Most Helpful Guy
If i had to guess, I'd say he is just saying it jokingly. But he sounds like a very rude, inconsiderate person. If i were you, I'd tell him that you don't like it, and that it makes you feel bad. I he doesn't stop, dump his sorry ass.
Most Helpful Girl
That's actually pretty rude. Most guys I know hate it when girls say "Do I look fat? Does this make me look fat?" and etc , so he might just be saying no to "get you off his back." You should address this with him and tell him to stop if you don't like it.