Chasing the Leprechaun 

A name for a woman who is known to be a gold digger. Prominently old white men with money are the primary target. When he dies, she gets his pot of gold!

Chasing the Leprechaun is the act of pursuing a rich old white guy for his money.

Chasing the Leprechaun by Sean Day Lou Swahili Swag September 1, 2016

Chasing the dragon or chasing dragons 

The term "chasing the dragon" or "chasing dragons" refers to a situation where someone is repeating a theme or pattern in life hoping to find the same results experienced a prior time. An experience of significant impact is the catalyst associated with good times, improvements, enhancements, happiness, pleasures, dreams coming true, etc. One is said to be chasing dragons when they seek to repeat this pattern hoping for the same results experienced the first time.

He has been chasing the dragon or chasing dragons looking for another high school sweetheart ever since they broke up.

That band has been chasing the dragon since their first single looking for another hit.

Chasing the dragon or chasing dragons by TrinityAuthor October 3, 2020

clout chasing 

when sad people try to gain popularity

hey, stop clout chasing dumbass

clout chasing by clout chasing April 29, 2020

Cheek chafing

when you are running so hard your buns start to get sore from constant friction

man, I got cheek chafing so hard the other day from running

Cheek chafing by Breckinbad February 20, 2015

chasing tail 

The pursuit of casual sexual relations, especially a male's pursuit of a female.

"I usually spend my weekends drinking at the bar and chasing tail"

chasing tail by deorum March 19, 2008

Chasing that ice 

When you are working hard to become richer.

Charles be chasing that ice, he been taking extra shifts.

I need to finish this essay. I be chasing that ice.

Chasing that ice by PartyArty December 5, 2019

chasing cars 

"Chasing Cars" is the third single from the UK band Snow Patrol's fourth album entitled Eyes Open. It was released on July 24, 2006 in the UK

The phrase "Chasing Cars" came from Gary Lightbody's father, in reference to a girl Lightbody was infatuated with, "You're like a dog chasing a car. You'll never catch it and you wouldn't know what to do with it if you did."

Let's waste time
Chasing cars
Around our heads

I need your grace
to remind me
to find my own

If I lay here
If I just lay here
Would you lie with me and just forget the world?

chasing cars by Eoin Maxwell January 13, 2008