Know When to Stop
How adorable. This guy wants to make the woman he likes smile. Oh, he’s still going on about it. That’s pretty cool, we guess. Wow, he just won’t let up about what he’ll do to make this woman smile. Look, man, there’s a point where your persistence comes off as downright annoying, and that point was several text messages above.
She already said she was cool with it, so why did you have to go 100% “nice guy” mode on her? You got the date, just show up and don’t be a jerk. Also, for the love of everything holy in this universe, do not wear a fedora on your date.