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This smart romantic comedy wrestles with the miseries of the mid-life, recycled dating scene. Having recently decided that he is through with romantic relationships (though not through with women), George has made an impulsive bet with his meddling sister that he will solve all his dating problems by “hiring” a mistress. Now, just two days before the “show and tell” dinner where he must produce said mistress to avoid losing the high-stakes bet, a mistress-less (and clueless) George tries to engage a 30-something theatre student to play his paramour for the dinner. A contentious though talented Meredith finds the assignment disgusting but needs the money and, truth be told, is excited by the acting challenge of a full evening of improvisation. While the antagonistic couple is attempting to fashion a convincing backstory for the dinner charade, sister Betsy suddenly appears, throwing Meredith and George into a frantic, ill-prepared improv a full day early. Amidst the chaos, Meredith and George gradually come to appreciate each other’s odd yet strangely sensible takes on life and relationships.