Calvin James is an aspiring stand-up comedian who, like most late twenty-something males, is forced to answer the eternal question: get married or continue living his extended adolescence. But after four years of patiently biding her time, Calvin's girlfriend, Liz, proposed marriage which sends Calvin on an emotional roller coaster. In his heart, Calvin knows that Liz is all the woman he needs, but he would quicker swap "till death do us part" for renewable every four years. However, as Liz sees it, the choice is now or never. The question remains, after living such a carefree whimsical life for so long, does Calvin have what it takes to leap into matrimony?