I'm dating a guy who is flat broke due to some bad luck and also doesn't have his own place. So far, we only hang around my apartment. I'm not rich by any means, but wouldn't mind buying dinner or movie tickets or a few drinks so we can hear a band. He's super embarassed about not having any money though. How can I pay for us to actually do something without hurting his feelings?
Most Helpful Girl
Buy tbings in advance. Get tickets for movies or plays ahead of time or online so when you get there he doesn't have to worry about paying or you having to offer :)2