 This message works here as she asked too many questions to answer and the conversation still be easy to follow. This message cuts out a lot of the sidetracks it would be easy to go down. It is short, succinct and communicates confidence as he is ‘positive’ their date will go well. 
Her: I like it, what time did you get in last night? Was it late? Oh god yep I don’t know how you people exist, do you drink loads as well?
Her: Nightmare, yes was a bit awkward. I was just waffling on to make it less so 🤣 will it now? Are you sure about that?
Her: Are you a little bit silly or no?

Positive. Define silly