Top Definition
Very risky move, trying to get to second base with a girl without knowing if she's going to be accepting. Similar to stealing a base in baseball.
I tried stealing second last night, which ended in her naming me as a fuckboy.
af FedoraFilms 18. december 2015
When you make out with a girl that has her boobs out, but you don't touch them.
Jon: So how'd your date go last night.
Newton: Not bad, only stealing second.
af Newtron Bomb 14. juni 2010
Hitting on a girl and grabbing her boobs before you kiss her.
Stealing Second -

Dude I totally stole second with Kate last night!
af Mr. Groper 18. januar 2015
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