Max and Caroline's plans to attract upscale clients to their dessert bar go awry when members of an arm-wrestling team become regulars. Meanwhile, Oleg ghost writes sexy messages for Max to send to Randy.
Grace returns from her European travels a new woman, but her elation is short-lived when she receives life-changing news; Karen teaches Will how to be better at phone sex; Jack has a yard sale to discreetly get rid of Estefan's annoying cuckoo clock.
After Will and Grace's parents get married, big changes are afoot for the gang. Will gets a teaching job and a beard, Grace decides to run for office, Jack prepares to settle down with Estefan and Karen goes missing.
Grace's accidental encounter with a curmudgeon she follows on Twitter smacks of romance. Meanwhile, Jack makes a very bad impression on Estefan's family, and Will helps Karen protect her most loved possession.
Will and Grace learn that their parents have made a surprising connection, Jack rebounds from his break-up with a new love, and Karen must choose between husband Stan and lover Malcolm.