by brettsterplow October 22, 2008

When you see the Mother and Daughter out on the town, and then they both see you and realize that they both have banged you from the dating sites.
"I ran into Suzie and Claudia on the town, I had no idea they were related. It was quite the Hat Trick Surprise."
by SRKJ August 2, 2022

The official term used to describe an event where the boss comes in sick and then shares it with everyone, despite knowledge that he is contagious.
Stemming from the October Surprise of Donald J Trump who contracted the deadly coronavirus and subsequently participated in multiple interactions with colleagues unaware of his existing positive diagnosis, infecting numerous members of his administration.
Stemming from the October Surprise of Donald J Trump who contracted the deadly coronavirus and subsequently participated in multiple interactions with colleagues unaware of his existing positive diagnosis, infecting numerous members of his administration.
"Hey Tina, our CEO Jim sure gave us an October Surprise with his awful cold this week. Half of the marketing team is on mandatory PTO now. He still wants to meet with you in person tomorrow about those sales reports, though. I recommend a hazmat suit..."
by FlagRaiser October 16, 2020

Dani: *Puts shorts on and reaches in pocket to find a dollar*
Jawsh: You lucky bastard, you just got a retarded surprise.
Jawsh: You lucky bastard, you just got a retarded surprise.
by J a w s h October 29, 2010

the act of gagging your drunk partner with your penis until they vomit on said penis and then quickly shoving your penis into your partners vagina/anus.
by jimmy McDoogle July 3, 2012

The sexual act of filling your asshole up with whipped cream then proceeding to fart said cream into your partner's mouth.
by Dirk Dasterdly August 13, 2021

Nathaniel had his lollipop surprise taken care of by Cameron as Sean, Jonathan, Ethan and Simon watch.
by PrayerHub May 28, 2021
