Spoiler Level: High
The Enterprise encounters Okona, a vagabond whose ship has broken down. While Geordi helps him repair his ship, he charms up the Enterprise crew, especially Transporter Chief J. G. Robinson (played by Teri Hatcher).
It's another fun character episode. Data's failure to understand any of Okona's jokes leads him to experiment with concept of humor. Luckily he goes to Guinan and not Pulaski. While Guinan may be a little rough on him, it's always done with a smile and a sympathetic tone. Watching Data try to learn humor is actually a little sad this time around; since I know he's not going to get it until he has his emotion chip installed in Generations, I know he's doomed to fail. The first time around there was the hope that he would make a breakthrough. Still, he closes out with the great line, "Take my Worf... please," which got a genuine laugh from me both times I saw it, so there is at least a little breakthrough there.
It's not long before trouble shows up looking for Okona; one ship with an irate father of a pregnant young girl, and another ship with an irate father of a young man who befriended Okona and now one of their family jewels is missing. It's not too hard to connect the dots; The two young kids are obviously starcrossed lovers, and Okona was helping them out. But the predictability of the main plot doesn't detract from its charm, and again, I think it's because of the strength of the performances of Okona and Picard.
I'm actually disappointed that the show never used Okona after this. I kept hoping he'd show up again because he's a really fun character, but alas, this is his only appearance.
I also find it somewhat amusing that although this episode has a strong guest appearance lead in Okona and a big name guest-star (at the time at least) like Joe Piscopo, the guest appearance everyone remembers this episode for is then-unknown Teri Hatcher! It just goes to show, you never can tell what people will remember you for.
UPDATE: While doing a IMDB search on Jeffrey Combs, I discovered that William O. Campbell, who played Okona, is the same Bill Campbell who played Jordan Collier in The 4400! Wow!