Henry throws a surprise birthday party for Tess and invites her sister, Brittany -- unaware that Tess can't stand her. At the party, Henry soon discovers why after Ian and Brittany strike up a relationship that threatens to put a wedge between his and Tess'.
Tess (who narrates the tale) attempts to fix up Ian and Maddie after becoming jealous that Ian and Henry are hanging around each other too much. But it's a match made in hell after Maddie tries to teach Ian how to dance for their first date.
Henry's and Tess' declaration that they are ""engaged to be engaged"" leads Ian to play yet another prank on Henry -- this time by setting it up to look like Henry did it with Maddie.