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.
Chapter 17 - ALLIE
Dean
Seen congregating with his former teammates in the ballroom, prompting Allie to worry about his impulsive nature and potential spontaneous proposal despite their previous agreement.
Chapter 18 - DEAN
Dean
Visits Joe Hayes under the guise of dropping off groceries to ask for his blessing to propose to Allie. After securing approval, he travels to Manhattan to ask his mother to borrow the family penthouse for the evening, successfully gaining her enthusiastic support and a promise of secrecy from his father.
Chapter 19 - ALLIE
Dean
Arranges an elaborate dinner at his mother’s penthouse under the guise of a special occasion before attempting to propose with a ring box. He becomes frustrated when Allie rejects the timing, arguing that four years together justifies moving forward now rather than waiting. After questioning her commitment and receiving a noncommittal answer, he abruptly ends the evening and leaves for the hotel downstairs.
Chapter 20 - ALLIE
Dean
Maintains a two-day silent treatment following an aborted proposal attempt before abruptly ending it when he spots Allie preparing to leave. Reveals he asked her father for permission, shocking her with the detail. Later texts from Newark to confirm he is staying at a hotel owned by Elijah’s family.
Chapter 21 - DEAN
Dean / Dean Sebastian Kendrick Heyward-Di Laurentis
Reflects on his failed proposal and debates the necessity of engagement with Garrett before accepting Allie's timeline. He later retreats to a private room where he happily accepts her counter-proposal and celebrates their new status the following morning.