island hopping 

a strategy for picking up women, named after the Allies' strategy used in World War II. It consists of using an uglier girl to get closer to her hotter friends, and then in turn using that girl to get closer to her hotter friends, jumping from girl to girl until you've reached your desired goal.

Have you heard of "island hopping"?
Yeah, of course I have!
Yeah, I started dating Agnus two years ago but I island hopped my way to Jessica

island hopping by Rad Warhawk June 29, 2011

Island Hopping 

island hop
when a guy dates a girl, breaks up with her. then goes out with a friend of hers. in the end to come back with the original girl

Dude, I'm gonna be with Chelsea then go with her friend to get her more interested in me. So I can come back when me and her friend are done. You gonna island hop? Yeah. Island Hopping works bro

Island Hopping by Machuski February 22, 2015

Island hopping Heather 

A woman who hops or goes from place to place to live. Not a couch surfer though. They take advantage of and live off of someone which is usually a much older man, because they can’t keep a job or get a home of their own. They lead the homeowner on to make them think they have a chance at a relationship but it never happens. Once she’s taken what she needs and they realize what she’s done and call her out she will act as if she’s been abused or taken advantage of to try to make herself look like she’s done no wrong and get sympathy from the next victim.

That girl is nothing but a island hopping Heather, she manipulates and uses these older men !

Island hopping Heather by Friend of Ms.Mf January 7, 2021