Dawson's Creek - Season 4 Episode 13
Hopeless

The senior trip is coming up and Joey needs to get the time off from work -not an easy task seeing that Drues mom is her boss. However, she decides to give her a few days off.... if she agrees to go on a double date with Pacey to accompany Drue and a wealthy girl named Anna Evans and make sure that Drue behaves himself. Of course this isnt an easy thing to do, and during their night out, Joey starts to get concerned over all the attention that Anna is bestowing on Pacey. Dawson has his own problems when he and Gretchen go out with her friends and he realizes the span in between their ages. Jack also (finally) gets some positive attention from Tobey.