Season 5 opens shortly after the Richard was left at the altar. As Richard plans to win New Christine back, Christine and Matthew disparage their lost loves. However, when Christine finds out Barb is being detained and may be deported, she runs to her side. Barb thinks a guy named Bongo can help her, so Christine and Matthew fly to the Bahamas to find him. Unfortunately, Christine loses her passport and ends up being detained in the Bahamas; they return 24 hours later with no Bongo.
Meanwhile, Richard finds out New Christine is over him and is moving on. And Barb's immigration officer flirts with her saying if she's in a sham marriage, he'll overlook it and reinstate her status. Barb and Richard announce their engagement.