I was probably the worst possible match for his speal because I grew up regularly sailing on my Grandpa’s boat and after moving to Florida it was something I really missed.

He found… someone who actually knew how boats work!

I once had a date with a guy who constantly bragged about his sailboat and how amazing he was at sailing.

I Started asking questions about said boat and he didn’t know what a jib was or even what kind of sailboat it was.

Bonus, after repeatedly bragging about how much money he had, asked for a separate check. Which, splitting a bill is fine, but to do it after specifically bragging about how rich you are?