Rebecca is still smarting from Evan Drake's departure to Japan. So instead of men, she focuses her energies on furthering her career - she figures that Evan Drake took all the key players from the company to Japan with him, and thus all those that knew she is a "washout" are now all gone - and buying a Mercedes. But realistically, her defences are weakened, so when Sam asks her out again, she accepts, albeit without much enthusiasm. Just as Rebecca and Sam are about to go on their first date, Rebecca's new boss, Greg Stone, comes to the bar. Rebecca, having a boss fixation, drops Sam at the sight of Mr. Stone. For her, it is love at first sight all over again.
Rebecca puts Sam off by telling him that from now on she'll only date men who can advance her career, and then she meets her younger-than-springtime new boss.
Sam goes to Mexico to open a new bar for the company, robbing Rebecca of her ""fiance"" and her only defense against the marriage proposal of her baby boss.
Sam finds himself attracted to both an old girlfriend and her grown daughter while Woody volunteers to be the clown at the boss' kid's birthday party Rebecca is planning.
Cheers gets another chance of losing a contest to their cross-town rivals at Gary's Old Towne Tap; this time the contest is for "Boston's Best Bloody Mary."
Rebecca tries to impress corporate headquarters by using her marketing skills to promote Norm's one man painting business and Sam tries to keep up with a sweet young thing wild about all kinds of sports.
Woody's rich girl friend doesn't fully appreciate his inexpensive but heartfelt birthday gift and Rebecca transforms herself to further her career prospects.
23 min
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