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Book Club Questions for The Five-Star Weekend by Elin Hilderbrand

Book Club Questions for The Five-Star Weekend by Elin Hilderbrand

Book club questions for The Five-Star Weekend by Elin Hilderbrand takes a deep dive into this novel about friendships and self-discovery. There will be spoilers so for more context about the novel, check out my spoiler-free review first.

I liked this novel overall! I think the concept is great. And I’m always a fan of books that focus on women friendships.

Let me know what you thought about the novel below!

The Synopsis

Hollis Shaw’s life seems picture-perfect. She’s the creator of the popular food blog Hungry with Hollisand is married to Matthew, a dreamy heart surgeon. But after she and Matthew get into a heated argument one snowy morning, he leaves for the airport and is killed in a car accident. The cracks in Hollis’s perfect life—her strained marriage and her complicated relationship with her daughter, Caroline—grow deeper.

So when Hollis hears about something called a “Five-Star Weekend”—one woman organizes a trip for her best friend from each phase of her life: her teenage years, her twenties, her thirties, and midlife—she decides to host her own Five-Star Weekend on Nantucket. But the weekend doesn’t turn out to be a joyful Hallmark movie.

The husband of Hollis’s childhood friend Tatum arranges for Hollis’s first love, Jack Finigan, to spend time with them, stirring up old feelings. Meanwhile, Tatum is forced to play nice with abrasive and elitist Dru-Ann, Hollis’s best friend from UNC Chapel Hill. Dru-Ann’s career as a prominent Chicago sports agent is on the line after her comments about a client’s mental health issues are misconstrued online.

Brooke, Hollis’s friend from their thirties, has just discovered that her husband is having an inappropriate relationship with a woman at work. Again! And then there’s Gigi, a stranger to everyone (including Hollis) who reached out to Hollis through her blog. Gigi embodies an unusual grace and, as it happens, has many secrets.

Book Club Questions for The Five-Star Weekend

  1. What do you think about the concept of a Five-Star Weekend full of a reunion with friends from different eras? Who would you invite and where you have your own Five-Star Weekend?
  2. Why did Hollis decided to host a Five-Star Weekend? How did she decide which friends to invite?
  3. Why do you think she invited, Gigi, someone she’s never met?
  4. What were your thoughts about the reveal that Gigi was having an affair with Matthew, Hollis’ husband? Why did Gigi agree to attend the weekend?
  5. What are some of the factors behind the tension between Hollis and her daughter, Caroline?
  6. We learn that Hollis and Matthew were going through marriage troubles before he died. Both Caroline and Matthew blame Hollis’ blog for the issues. What are your thoughts on that?
  7. Each of the friends are all going through their own individual issues. What was you impression of all the women? Was there a storyline you were more engaged with? Which one?
  8. Why did Hollis leave behind Nantucket (other than for summer vacations)? And what brought her back there after Matthew died?
  9. A good portion of the novel is focused on how friendships can define us but also how we sometimes grow apart. Why do you think some friendships don’t last while others are in it for the long haul?
  10. Eventually, Gigi is forced to reveal the truth about her affair with Matthew. What would you have done if you were Hollis? Were you surprised she never told the other women about this?
  11. The novel is focused on friendships but there is a side story where Hollis reconnects with her high school boyfriend, Jack. What were your thoughts on this storyline?
  12. In what ways did the Five-Star Weekend impact each of the women?
  13. What did you think about the ending? What’s next for all the women?

Additional Recommendations

Hope you enjoyed book club questions for The Five-Star Weekend! Here are some more recommendations along with links to book club questions.

The Celebrants by Steven Rowley

Another book that covers friends reuniting among personal crisis is The Celebrants by Steven Rowley.

It’s been a minute—or five years—since Jordan Vargas last saw his college friends, and twenty-eight years since their graduation when their adult lives officially began. Now Jordan, Jordy, Naomi, Craig, and Marielle find themselves at the brink of a new decade, with all the responsibilities of adulthood, yet no closer to having their lives figured out. Though not for a lack of trying. Over the years they’ve reunited in Big Sur to honor a decades-old pact to throw each other living “funerals,” celebrations to remind themselves that life is worth living—that their lives mean something, to one another if not to themselves.

But this reunion is different. They’re not gathered as they were to bolster Marielle as her marriage crumbled, to lift Naomi after her parents died, or to intervene when Craig pleaded guilty to art fraud. This time, Jordan is sitting on a secret that will upend their pact.

A deeply honest tribute to the growing pains of selfhood and the people who keep us going, coupled with Steven Rowley’s signature humor and heart, The Celebrants is a moving tale about the false invincibility of youth and the beautiful ways in which friendship helps us celebrate our lives, even amid the deepest challenges of living.

Check out my book club questions here.

We Are Not Like Them by Christine Pride and Jo Piazza

A novel with a more serious tone but also focuses on evolving friendships is We Are Not Like Them by Christine Pride and Jo Piazza.

Jen and Riley have been best friends since kindergarten. As adults, they remain as close as sisters, though their lives have taken different directions. Jen married young, and after years of trying, is finally pregnant. Riley pursued her childhood dream of becoming a television journalist and is poised to become one of the first Black female anchors of the top news channel in their hometown of Philadelphia.

But the deep bond they share is severely tested when Jen’s husband, a city police officer, is involved in the shooting of an unarmed Black teenager. Six months pregnant, Jen is in freefall as her future, her husband’s freedom, and her friendship with Riley are thrown into uncertainty. Covering this career-making story, Riley wrestles with the implications of this tragic incident for her Black community, her ambitions, and her relationship with her lifelong friend.

Check out my book club questions here. Happy reading!