Dean Sebastian Kendrick Heyward-Di Laurentis
Chapter 6 - Logan
Dean
He sends a series of messages to the group chat expressing disbelief that Logan and Grace are secretly dating, prompting a snarky reply from Logan about pink dildos.
Chapter 11 - Dean
Dean / Dean Heyward-Di Laurentis
Rehearses a marriage proposal to Allie Hayes while receiving blunt feedback from Garrett and Logan. He reveals he abandoned a Harvard Law track after a high school relationship trauma, only to find commitment through Allie nearly four years ago. He confirms the ring's massive size, discusses Tucker's upcoming wedding and daughter Jamie's third birthday, and shuts down Logan's suggestion to gift them the Alexander doll.
Chapter 12 - ALLIE
Dean / Dean Heyward-Di Laurentis
He teaches and coaches hockey and volleyball at an all-girls private school in Manhattan, possesses a wealthy family with a private jet, and maintains a highly sexual relationship with Allie.
Chapter 16 - DEAN
Dean / Dicky
Narrates the wedding reception while wearing an expensive Tom Ford suit and teasing his girlfriend Allie about marriage. Briefly panics over asking her father Joe for his blessing, reflects on drifting college friends and deceased friend Beau Maxwell, then joins the group's explicit speculation about Coach Jensen's sex life.