This season starts off with Brian (Steven Weber) feeling like he is actually in love. Gone are the days of playboy, one-night stands, because he has spent hours on a date with Alex (a character introduced in the past couple of seasons) just talking. Of course, everyone else is skeptical about Brian's new perspective. Will this new relationship last? This is just one of the running story arcs in this season.
Another series of events follows Lowell's (Thomas Haden Church, recently seen in Spider Man 3) divorce from his wife Bunny. Just after the divorce is finalized, the two start sleeping together again, but Lowell seems to get the wrong impression about the possible patching of their relationship, that is until he finds out Bunny has a fiancé on the mainland. So now Brian and Joe (Timothy Daly) have to help console Lowell, their new roommate.
One of the major events in the season is the two-part episode, "Joe Blows," where the stress of running Sandpiper Air, acting as everyone's go-to guy and just generally being pulled in every direction causes him to leave Nantucket. By the end of these episodes, Brian learns just how hard it is to run the business and when Joe finally comes back, the two become full-partners in the company.
The season wraps up with Helen (Crystal Bernard) getting proposed to by her boyfriend Davis and Joe gets a loan to help out Sandpiper's financial troubles. When Joe returns to the island to find Helen engaged, the two start to congratulate each other in their good fortunes, but the congratulations seem to rekindle their old flame. This, of course, comes as a shock when Brian walks in on the two in bed.
Wings: The Fifth Season is a good purchase for existing fans of the show, but unless you've already invested in the series, you can pretty much skip this DVD set.