When Heath Petersen licks one or multiple fingers and then rubs the clitoris in a clockwise motion 360 degrees in order to obtain organisms prior to sexual relations.
She couldn't get off so I gave her the roundabout.
by HPuptopdowntown October 13, 2013
When a person puts ones fingers on ones clitoris and moves in a circular motion. This action can be done to oneself or by others.
Jimmy: Hey did you hook up with that girl last night?

Johnny: Yeah, I was roundabouting her so good.

Jimmy: Yeah bro I heard you are a pro roundabouter.
by ProRoundabouter June 26, 2021
Telling a joke connected to a prior joke or topic.
At ~40m 55s in Season 1 Episode "Are We Guilty of Stealing YouTube Content" of the All In Podcast: Co-host Crayator jokes, "I'm a talker, not a setter-upper, unless I want to paint a wall and do some carpeting." This is a reference to the bit (discussion) at the beginning of the podcast where co-host Loserfruit joked that she had not believed Crayator had done the painting in his new office.

Crayator then coined the term, "Roundabout Comedy."
by NAEastBot March 19, 2020
When two people are in a heated argument, but neither is talking about the same thing.
John and Harold have both been sleeping with karren. When John confronted Harold about dipping in his sauce, Harold began yelling at john taunting him with the delicious sauce. John was referring to Harold sleeping with Karren, while Harold was referring to the delicious bottle of ranch in the fridge. They are both arguing about different things, Classic Cincinnati Roundabout!
by Harrison_P_Thatcher June 4, 2014
When you cut a hole in a cactus and proceed to fuck it
Hey bro wanna come to the desert tonight and do a Texas Roundabout with me?
A technique in which one can give themselves an anal eating.

Step 1: Clamp open your asshole using some clams.
Step 2: Grab your trusty pair of boxing gloves and beat the hell out of your asshole.
Step 3:Then sauce your asshole with barbecue sauce.
Step 4: Then proceed to play Roundabout at max volume while going to town on your asshole.
Ex:"Yeah dude, last night I went to town on my asshole using the roundabout technique."

Ex:"I'll be the roundabout! Eat your asshole out 'n out!"
by John_Pickle December 19, 2019
When a girl appears to be fit from behind, you approach and she turns around to reveal she is in fact minging
Guy 1:"That girls looks fit, I'm going in"

Guy 2:"Yea go for it"

2 minutes later....

Guy 2:"Was she not game?"

Guy 1:"Naaa mate, roundabout syndrome"
by carltondcb16 May 12, 2011