Ruby Capote is a newspaper columnist who writes humorously about things that happen around her. Often using her friends and her day-to-day encounters as her material. Ruby wants out of her current relationship and decides getting a job in New York City, leaving Doug in Boston, is the way to do it, a perfect passive-aggressive maneuver. So she sends off her resume and when she doesn't hear back, she sends off a letter with a six-pack. This time she gets a reply and it's clear she has found her kindred spirit in her new boss.
Though it's a nickel ante game, as time goes on, the stakes raised are more than the nickels on the table. While all of her friends seem to be willing to take risks and thus eventually get what they want in their lives, Ruby is $27 dollars down, in nickels. Ruby manages her relationships like her poker game, folding early so she doesn't have to find out if she lost. But now there is something at stake for Ruby and her girlfriends know it, even if Ruby doesn't. It turns out that her new boss, Michael, just might be Mr. Right. But can Ruby play the game out?
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