There's Something About Allison

Finch's old buddy Bert - now a transsexual named Brandy - joins Finch as a couple at their high school reunion in order for Finch to arrive with a beautiful blonde while Bert/Brandy can attend without revealing his true identity. At the reunion, the girl they both competed for in high school hits it off with Brandy and reveals her past crush on Bert. Meanwhile, Maya and Elliott decide to become intimate with no strings attached.

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S07E14 - Rivals in Romance