He was doing well, but really shot himself in the foot there at the end… Another classic case of over-gaming a girl.
This is NOT a situation where you want to “Agree and Amplify.”
When you’re courting a girl (especially online), it’s counter-productive to escalate things because you ALWAYS risk scaring a girl away. By talking too much early on, you have a higher chance of screwing up by saying something stupid, beta, or overly offensive. It’s easier to feign seriousness with body language (i.e. a smirk) or to recover from something you said immediately when you do it in person. It’s also less easily misconstrued as game, especially if your intentions weren’t devious.
This is another reason I recommend that you refrain from communicating too much before a first date. It’s especially hard to make a girl more attracted to or comfortable with you when you aren’t dealing face to face (this includes IMs, texting, emails, etc.).
Let’s look at what went wrong in the above example.