You want to be funny in a charming way and a bit of a tease (the annoying part). So make the occasional dad joke, tell a funny anecdote, make funny observations and tease her a little bit but not in an insulting way. But don’t go full stand up comedian and spill out your inner clown or Bill Burr, most women aren’t attracted to that at all.
Why not too funny and annoying?
You want to be funny in a charming way and a bit of a tease (the annoying part). So make the occasional dad joke, tell a funny anecdote, make funny observations and tease her a little bit but not in an insulting way. But don’t go full stand up comedian and spill out your inner clown or Bill Burr, most women aren’t attracted to that at all.
Funny, not a clown, you want to appear confident.
Annoying I wouldn’t know why, but I guess it could help appearing more natural.