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The Winter Wedding Plan--An unforgettable story of love, betrayal, and sisterhood by Olivia Miles (32)

Discussion Questions

  1. When Charlotte is visiting with her single, childless cousin, Bree, she gets a little bit jealous of Bree’s life, thinking, Oh, the luxury. To live without a care in the world. To live only for yourself and your own whims. But Bree is lonely and heartbroken. Can we ever really tell how happy another person is? What strategies do both Bree and Charlotte use to hide their sadness from their friends and family?
  2. As Charlotte struggles to stand on her own two feet, she worries that she’s not independent enough to be a good role model for Audrey. Is she right about showing Audrey the value of independence, or is it also important for her to show her daughter how (and when) to ask for help? What makes a mother a good role model?
  3. Charlotte agrees to pretend to be Greg’s fiancée for the Frost holiday party to land the account for Kate’s event planner firm. Was this the right move, professionally? How would you feel if your employee made the same deal? Would you have reacted the same way Kate did, or would you have handled it differently?
  4. Greg’s mother, Rita, was also a single mother with no support from Greg’s father. How was her approach to single motherhood different from Charlotte’s? What other events and obstacles may have influenced her more reserved style of parenting?
  5. Charlotte is not a great cook, and yet she’s able to pull together a somewhat decent meal for Greg and Rita at the last minute. Have you ever had a similar “fake it until you make it” moment? What was that like? If you were in a similar situation, what would your go-to recipe be?
  6. In what ways did motherhood change Charlotte? In general, how does becoming a parent shift a person’s identity?
  7. Later in the book, Charlotte and Greg debate whether the Christmas holidays bring out the best or the worst in people. What do you think? How do the holidays change the characters in the story, for better or worse? What are some examples from your own life of people behaving exceptionally well or exceptionally badly around the holidays?
  8. Charlotte spends so much of the book worried about making Audrey’s first Christmas special. What do you think is the ideal “baby’s first Christmas”? If you have kids, what was your first Christmas with them like? If you don’t, can you imagine what kind of traditions you’d like to introduce to your children, should you choose to have them?


Author Questions

1. The book opens with Charlotte making a “Thanksgiving Day resolution.” Have you ever made a resolution at a nontraditional time? If so, what prompted that resolution?

I don’t tend to make New Year’s resolutions, but instead, randomly promise to change and grow as things pop up throughout the year. As in Charlotte’s case, some things just can’t wait until year end!

2. This novel is filled with wonderful Christmas traditions, from the town tree lighting to the cookie swap at the local tea shop. What are some of your favorite holiday traditions?

One of my favorite holiday traditions is high tea with my daughter, and she also participates in the Nutcracker (on ice!) every year. Christmas through a child’s eyes is so much more magical, and this was something I tried to tap into with Charlotte and Audrey. The holiday is no longer about Charlotte, but in trying to make it special for her daughter, she is able to relive some of her fondest memories and traditions and create new ones, too.

3. There are so many different, vibrant characters in Misty Point. Do you have any favorites? Are there any characters you relate to more than others?

I relate to Bree quite a bit. I’m a vegetarian, as is she, and I’ve been known to tackle home remodeling projects that I then wished I had never started. But in fairness, I’m also impulsive like Charlotte and a perfectionist like Kate, so I relate to each character in my own way. While I couldn’t say that one character is my absolute favorite, Charlotte holds a special place. She’s very real to me.

4. What’s your favorite holiday book?

I always read my daughter ’Twas the Night Before Christmas around the holidays, and I’d have to say it’s a personal favorite.

5. Over the course of your last book, One Week to the Wedding, and in this novel, Charlotte really comes into her own and grows as a person. Is your writing process for character development different when it happens over the course of two books instead of one? Why or why not?

Yes, my process is different when a character is developed over multiple books rather than one, because it affects the pacing and allows me to build up their backstory in a more present and impactful way. I enjoyed having the time to show the two sides of Charlotte and better explain her conflict and choices in a way that I think makes her more relatable to my readers.

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