- 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?
- Why did Hollis decided to host a Five-Star Weekend? How did she decide which friends to invite?
- Why do you think she invited, Gigi, someone she’s never met?
- 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?
- What are some of the factors behind the tension between Hollis and her daughter, Caroline?
- 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?
- 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?
- Why did Hollis leave behind Nantucket (other than for summer vacations)? And what brought her back there after Matthew died?
- 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?
- 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?
- 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?
- In what ways did the Five-Star Weekend impact each of the women?
- What did you think about the ending? What’s next for all the women?
The Five-Star Weekend by Elin Hilderbrand
More discussion at bookclubchat.com. These questions contain major spoilers.