Went to a bar/restaurant and had dinner at the bar with my roommate, he has a crush on one of the bartenders working at the bar that night. They seemed to be really into each other but we learned that it's her last night working. So he's a bit upset as we were on our way home and I kept telling him to go back and talk to her more because it's pretty much his last chance to spend time with her, but he wouldn't turn back (he's got some huge confidence issue). Once we got home I told him "I'm going back to have some drinks, and you're coming." He still wouldn't go even though I was literally being his drill sergent. I kept trying to get him go back and he kept thinking about excuses. In the end I told him I'm walking there in the rain unless he picks me up on the way, that's how I got him to get in his car and drove there.
So we got there, had some drinks, talked his bartender crush, and found out she has a bf. We had a blast, all is good. Awesome night for me LOL.