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This can be used for either a male or female when their significant other is currently incarcerated. When they go on a "date" they will get the customary visit with the inmate. People that consider a jailfriends a real relationship are usually either major losers or fucked in the head so bad that somebody in the outside world wants to be with them.
Bob: Is your wifes friend Tina single?
Scott: Yes and no. She has a Jailfriend she goes to visit every once in a while.

That chick can't find a normal guy to put up with her bullshit so she went and got a Jailfriend.
by Therealdeal1984 February 22, 2012
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