I'll start with the good part, which earns the episode its points: The B-story involving Data following Guinan's advice to learn humor and taking lessons from a holographic stand-up comic (Joe Piscopo) ends up working reasonably well. Joe Piscopo isn't funny in these scenes, but Data is by definition an inspired straight man to a (would-be) comic persona. The scene where he gives his performance to an audience that laughs no matter what he does is both funny and sad; Data simply doesn't understand humor and maybe never will.
As for the main story, it's one of the most hoary and forgettable things in TNG's run. The Enterprise rescues Captain Okona (William O. Campbell; where's Bruce Campbell when you need him?) from his disabled ship. Okona spends his time aboard the Enterprise making high-spirited jokes, hitting on women, and in general being the type of Personality that requires a capital letter. (Wesley idolizes him ... which makes Wesley an even bigger nerd than I thought.) I suppose nothing says "swashbuckling scoundrel" like a ponytail and a three-day beard. One woman taken by Okona's charms is Teri Hatcher — yes, Teri Hatcher — whom Okona beds in record time.
The plot is a pedantic bore masquerading as light comedy. Okona is either in the middle of or the cause of a dispute between two feuding families. Is he the father of the pregnant girl whose father is really mad? Did he steal the crown jewel from the other family? Or is there something else here going on involving hopeless rehashed scraps of Romeo and Juliet? The episode makes it impossible for us to care, particularly in the awful climactic scene where all the parties are aboard the Enterprise and the air is finally cleared — in one of the worst-acted and worst-directed scenes I can remember on this series.