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"cave dating", "cave dater" or "dating in a cave" is a term meaning that you and your circle of friends tend to date people that are all in another circle of friends. It becomes as though you cannot escape dating this same other circle of a cave that you cannot find an exit to. Each friend seems to be connected to another friend...who's connected to another friend...and it never ends.

Often it feels like you are dating the same person over and over again and is extremely difficult to get out of. Unless you devastatingly break up with a native (one of the persons in the other circle of friends) in which case, no natives can touch you and you are exiled from the cave. Until you find a new cave...
Mike, Cory, Stephen, and Greg are all friends. Kelsey, Natalie, and I were each dating one of them. When Natalie and Cory broke up, she started dating Stephen. We're all going to be cave dating them for a long time.

Bree: "Kyle asked me out last night."
Gabby: "You need to get out of that cave, honey"
Bree: "I know, I've been cave dating this whole year."
by ohmygawditsgabx April 05, 2009
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