According to Jim Recap: When You Wish to Be a Star (Part 2)
In When You Wish to Be a Star (Part 1), Dana finally landed a new job as a Creative Director for an ad agency. Once there, she found that the family for the ad campaign was totally wrong, and when Cheryl showed up, she was perfect, and the family ended up with a free cruise. Once on the cruise, however, Jim was found to be a less-than-ideal father for the video, and he was replaced by an actor. When he found out that Cheryl had to kiss Ted, the actor playing the father, he was steamed. But if they quit the job, they had to pay for the cruise, so he pretended to go along with it.
Andy, who also managed to get a free cruise by agreeing to be Dana's gopher, helped Jim to score a job as an extra in one of the scenes so that he could keep an eye on Cheryl and Ted. Jim's role is as bartender Ernesto, and he jumps into it with gusto, , drawing himself a mustache, and trying to toss mixing cups and bottles, to spectacularly bad results.
When Jim pulls out his harmonica, and proves that he simply cannot do the job of pouring the drinks and then stepping back to let Cheryl and Ted enjoy their time together, he is quickly replaced - by Andy.
Later on the deck of the ship, as they pull in to Mexico, Jim is frustrated by Ruby and Gracie. The kids are told to get their dads up on stage for the hat contest (like musical chairs, but with hats on the head, instead of sitting in chairs). Gracie pulls Ted on stage, and Ruby is about to go with her when Cheryl gives her The Look and with a frown, Ruby takes Jim's hand. Once the game gets underway, a diving Jim elbows Ted in the face for the hat, and then everyone is mad at him - even Cheryl.
Deciding that he needs to make up to her, Jim decides that he will find Cheryl and try to apologize. But when Jim goes to the dock to try to catch her before she kisses Ted, to let her know that he's really okay with it, that he trusts her, Jim finds Dana, wearing a wig and kissing Ted! It's the best news possible! He could be his selfish self and get the free cruise and still get his way!
