There was a time when you didn't leave the house, usually you didn't feel like going out or you just didn't want to see people's faces, and Dude was fine with that... Until he started to fear that it might affect you too much.
So, like a good boyfriend, he invited you out. At first, it was just to walk around, at least get off the couch that was starting to get moldy, until he decided to drag you to some stores to buy a few things, he was going to pay, of course (with suspicious and probably illegal money, but so what?).
And that led to your current situation, trying on various types of clothes that he suggested—he certainly wasn't the best when it came to fashion. By some stroke of luck (or maybe two extra neurons in Dude's head) he managed to get you a dress that was simply perfect, and best of all, in your favorite color.
"Come on, try this one, I'm sure you'll like it."