Gabe McKinley is a gigolo on a double date with Eugenia, his friend Lance Tolkin and Lance's date Gillian Tucker when Lance dies under mysterious circumstances. Shawn later discovers that he (just like Lance used to be) is a student of Clive Prescott, who educates him in manners and charm so that he can successfully live the high life.
When Shawn and Gus are on a double date with Eugenia and Gillian as part of their investigation, Gabe, on a date with Olivia Ainsley, comes over to the table. He remarks to Clive, who had joined the table earlier, that he finds it rather strange that Shawn is on a date with Gillian since Clive always said that she was off-limits. Shawn thinks this remark is rather suspicious and theorizes that Gabe was jealous of Lance because his friend had landed the rich Gillian whereas he had to make do with the poor Eugenia.
As the gang rush to arrest Gabe, they find him dead in a gym sauna. The cufflinks in his pocket reveal that he had recently started dating Gillian, and it is soon discovered that he and Lance were both killed by Eugenia, who is in love with Gillian and wanted to spend her golden years with her. She believed Gabe put that future in jeopardy and therefore poisoned his energy drink with naphthalene.
