A Deep Dive Into ‘The Five-Star Weekend’ Cast’s Real-Life Relationships
The Five-Star Weekend is 2026’s perfect summer binge. The Peacock series, based on Elin Hilderbrand‘s book of the same name, follows Hollis Shaw (Jennifer Garner), a famous cook and best-selling author, who is reeling from the loss of her husband.
She plans a weekend getaway at her house on Nantucket with three friends from different stages of her life: childhood bestie Tatum (Chloë Sevigny), college best friend Dru-Ann (Regina Hall), and her mom friend Brooke (D’Arcy Carden). When Gigi (Gemma Chan) shows up, Hollis must confront her past as the secrets hidden under her picture-perfect life rise to the surface.
While The Five-Star Weekend focuses on friendship and family, there’s plenty of romance to enjoy, from first loves to affairs. But what about The Five-Star Weekend cast in real life? Swooon is doing a deep dive into the relationships and dating histories of the all-star ensemble.
The Five-Star Weekend, Season 1, Streaming Now, Peacock
Chloë Sevigny
Sevigny stars as Tatum McKenzie, Hollis’ childhood friend. The actress has been married to Croatian art gallery director Siniša Mačković since March 2020. Just a few months later, they welcomed their son, Vanja, who made a special appearance at The Five-Star Weekend premiere!
D'Arcy Carden
The Good Place alum stars as Brooke Kirtley, one of Hollis’ mom friends. Carden had the most adorable meet-cute with her husband — they crossed paths at Disneyland! Carden and her husband, executive producer Jason Carden, have been married since 2010.
Jennifer Garner
At the center of The Five-Star Weekend is Hollis Shaw, played by Garner. Like her character, Garner has had a complicated love life. She was married to Scott Foley from 2000 to 2004 and dated her Alias costar, Michael Vartan. She married Ben Affleck in 2005, and they have three children together: Violet, Fin, and Samuel. Garner and Affleck split in 2015.
Garner started dating businessman John C. Miller in 2018. They broke up in 2020, but they got back together in 2021 and have been together ever since.
Timothy Olyphant
Timothy Olyphant plays Jack, Hollis’ first love, who comes back into her life years later. As for Olyphant himself, he’s been happily married to his college sweetheart, Alexis Knief, since 1991. They have three kids, Vivian, Grace, and Henry. Vivian notably played Olyphant’s onscreen daughter in Justified: City Primeval.
Gemma Chan
Chan stars as Gigi Ling, one of Hollis’ new friends with a secret. Chan has been dating actor Dominic Cooper since 2018. Before that, she was in a years-long relationship with Jack Whitehall.
Judy Greer
Judy Greer, a longtime friend of Garner’s, plays Electra in The Five-Star Weekend. Greer has been married to Dean E. Johnsen, a former executive producer of Real Time with Bill Maher, since 2011. They met on a blind date. Johnsen has two kids from a previous marriage.
Henry Eikenberry
Henry Eikenberry stars as Dylan Leclaire in the Peacock series. He’s currently dating model Sophie Rothschild.
David Denman
David Denman plays Kyle McKenzie, Tatum’s husband, in the series. The actor has been married to actress Mercedes Mason since 2014. They have two kids: Caius (born in 2018) and Sagan (born in 2021).
Rob Huebel
Rob Huebel plays Charlie Kirtley, Brooke’s husband, in The Five-Star Weekend. Huebel has been married to his wife, news anchor Holly Hannula, since 2015. They welcomed their daughter, Holden, in 2016.
Regina Hall
Regina Hall stars as sports agent Dru-Ann Jones, Hollis’ college best friend. When it comes to her personal life, Hall remains private. She opened up about love in a 2022 People interview: “A beautiful world comes from a beautiful heart; that’s probably the best way to be beautiful. I’ve dated some men that haven’t all been traditionally handsome, but then you fall in love and you’re like, ‘They’re such a good human being.’ They actually get more beautiful.”
Josh Hamilton
Josh Hamilton plays Matthew Shaw, Hollis’ late husband. In real life, Hamilton has been a husband to Lily Thorne since 2005. They have two children.
Roberta Colindrez
Roberta Colindrez, who plays Sunny in the Peacock series, appears to be single. Colindrez keeps her personal life out of the public eye for the most part, but the Vida alum was linked to Shailene Woodley in the past.
Tory Devon Smith
Tory Devon Smith plays John Mark in The Five-Star Weekend. He hasn’t addressed his relationship status publicly, but he appears to be single.
Harlow Jane
Harlow Jane stars as Caroline Shaw, Hollis and Matthew’s daughter. The 23-year-old prefers to keep her personal life out of the public eye, so it’s unclear what her relationship status is. Fun fact: She’s Patricia Arquette‘s daughter!
West Duchovny
West Duchovny plays Tatum and Kyle’s daughter, Aubrey. Duchovny, the daughter of David Duchovny and Téa Leoni, hasn’t publicly revealed whether or not she’s in a relationship.
