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Crossing the Rubicon 

Crossing the Point of No Return. Named after Julius Cesar, who according to lore crossed said river into Rome, effectively declaring war.
I was Crossing the Rubicon the moment I thought he was too stupid to notice that I slept with his Girlfriend. He beat my ass so hard that to this day I twitch every time I hear the name Sasha.

Who's Sasha?

*twitch*
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Crossing the streams bad 

When something is as bad as Egon's explanation of crossing the streams from Ghost Busters:
"Try to imagine all life as you know it stopping instantaneously and every molecule in your body exploding at the speed of light."
"Right. That's bad."
It's supposed to be really bad... No, I mean like, crossing the streams bad!

Crossing Jordan 

Biblical metaphor of the ancient Hebrews crossing the Jordan River, commonly used in spiritual songs to represent death and passage to the afterlife.
I know that you are heavily wounded, but crossing Jordan is not an option!
Crossing Jordan by Roger Kint August 26, 2010

crossing borders 

When you have a "friend" sleeping in bed with you and you are "crossing borders" by having sex, feeling eachother up, etc. you on one side, your "friend" on the other. then you cross borders, that the girlfriend sets up, and "do it". usually tiedown free.
Danny and Jade wanted a little fun, but Jade didn't want him crossing borders.... He did anyway, now she's knocked up.
crossing borders by crossedoverbaby November 22, 2011

Crossing Sheaths 

The act of "accidentally" rubbing your vagina up against another womans's vagina.
"Sure, I'll move in with you guys! But under one condition, You, me and Robert can have a threesone. Unless you're not comfortable with the act of crossing sheaths.. >;]."
Crossing Sheaths by lolwutRon January 6, 2009

crossing guard teemo 

Some fat kid, with coconut hair.
Look at that wild crossing guard teemo, what a faggot.

Crossing it up, Catholic Style 

A handshake in the motion of the Catholic cross. It starts out as a normal handshake, then the hand position is changed so just the fingers are connected. From that point, the movement is up, down, then left to right and vice versa. The left to right movements should be done to the direction of the coolest person taking part in the shake. After the shake is done, it is optional for one to say "Cross it up," and the other to finish it by adding on "Catholic Style"
Person one: Oh look, Johnny and Tony are crossing it up, catholic style!
Person two: Yeah, they really must love Catholicism!!
Person three: STFU you idiots, catholics suck