This may be a repeat, if not, it’s not my best
Yankel had never spoken to girls his entire life, and when it came time to date, he didn’t know what to talk about. Anticipating awkward breaks between conversation, he asked his rebbe what to talk about.
rebbe: talk about family
Yankel: and when I finish talking about family
rebbe: talk about sports
on the date…
Yankel: do you have any brothers?
girl: no
Yankel: do you like baseball?
girl: no
Yankel: if you had a brother, would he like baseball?