About What to Wear

He told me he wants me to wear a different outfit every time we meet. Apparently, he used to buy clothes for the women he dated in the past, but says he can’t do that now because he doesn’t have the money. I know it’s partly my fault for always wearing the same types of outfits, but it hurt being told to wear something different every time when he used to buy clothes for the women before me but won’t buy any for me. It made me feel looked down on. Maybe I should have said, “I don’t have many clothes either,” and hinted that I wanted him to buy me some, but that’s just not my personality. Also, the reason I tend to wear similar outfits is that our dates are hotel-only. When we go somewhere stylish, like a restaurant, I change my outfit and dress up nicely each time. To be honest, since we only go to hotels, I figured my clothes weren’t really being seen much, so I’ve mostly been wearing simple, fitted dresses. I do change the color and style each time, though. He says he wants me to dress up as if I were going on a date with my boyfriend every day, but… I know this is something I should work harder on, but I can’t help feeling irritated when I hear that the women before me were treated better. What do you think?