Jennifer Garner’s new onscreen romance with Timothy Olyphant comes with decades of real-life history behind it.
People reported that Garner reunites with Olyphant in Peacock’s The Five Star Weekend, an adaptation of Elin Hilderbrand’s 2023 novel.
Garner plays Hollis Shaw, a celebrity chef and author rebuilding her life after her husband’s sudden death.
Olyphant plays Jack, Hollis’ high school sweetheart, who reappears during a Nantucket weekend meant to reconnect her with friends from different chapters of her life.
Garner Said the Trust Was Already There

Garner told People that working with Olyphant again felt natural because they had known each other for so long. She said their shared “trust and history” made the onscreen romance easier, adding that it was fun to arrive on set and “hit the ground running” with someone she already knew well.
Entertainment Weekly reported that Garner and Olyphant first worked together on the 1997 indie film 1999. They later reunited for the 2007 romantic comedy Catch and Release and the 2016 ensemble film Mother’s Day.
Garner also told People that she has known Olyphant’s wife for years.
Garner also reflected on Catch and Release, saying she recently learned the film has built a following she had not fully realized. She told People it was gratifying to discover that the 2007 romantic comedy had “this whole life” she did not know about.
Garner Helped Bring Olyphant Into the Show
Garner is also an executive producer on The Five Star Weekend. Showrunner Bekah Brunstetter told People that Garner was interested in working with actors she already had a connection with for Hollis’ two major male relationships, which helped lead to both Olyphant and Josh Hamilton being cast.
Hamilton plays Matthew, Hollis’ late husband. Olyphant plays Jack, the high school sweetheart who becomes part of Hollis’ emotional reckoning after Matthew’s death.
The Series Is Also About Female Friendship
Garner said the romance was only one part of what drew her to the project. She was also excited to work with an ensemble of women whose characters have full, complicated storylines.
The series stars Regina Hall, Chloë Sevigny, Gemma Chan and D’Arcy Carden as women connected to different parts of Hollis’ life. Garner told Entertainment Weekly that female characters are often separated into narrower roles onscreen, while The Five Star Weekend gave her a story centered on sisterhood.
People reported that Hollis brings friends from different eras of her life to her Nantucket home after Matthew’s death, childhood friend Tatum, college friend Dru-Ann, mom friend Brooke and surprise guest Gigi.
The Five Star Weekend premiered July 9, and all eight episodes are now streaming on Peacock.
