By Beth Kendrick
New American LibraryMay 2014

Trade Paperback336 pages, $15.00, ISBN: 9780451465856
Subject: Women's Lives / Relationships / Personal Challenges

  1. Louis L’Amour wrote, “There will come a time when you believe everything is finished. That will be the beginning.” Are there parts of your own life that bear this out? What do you think about this as a slogan for the town of Black Dog Bay and the heartbreak tourists? What other slogans might be appropriate?
  2. Summer and Ingrid establish an unorthodox mentor-mentee relationship, in which they both learn from each other. What are the most valuable lessons each learns? Think about mentors you’ve had in your own life—do you think you changed their lives, even as they were changing yours? How so?
  3. The Whinery provides humor, support, and a sense of community to women struggling to recover from romantic setbacks. If Jenna decided to open a second location of the bar in your town, what amenities would you add? What would your signature cocktail be called, and what would be in it?
  4. Lavinia Leighton, the founder of Black Dog Bay, was saved from drowning by a big black dog, which often represents depression in Western literature. Profound loss can result in profound life changes and spiritual awakenings. In your own experience, which factors predict whether someone will “sink or swim” after an unbearable heartbreak?
  5. Summer is a born adventurer in many ways, including her reckless approach to romance. Paradoxically, she uses flirtation and physical “intimacy” to keep men at a safe emotional distance. What makes Dutch different, in her eyes? What do you think he sees in Summer that makes him respond to her differently than to all the other women who have asked him out?
  6. In some ways, Hattie Huntington exemplifies the phrase “money can’t buy happiness”. What do you think her greatest fear is? Her fondest wish?
  7. Hollis tells Summer that the mystical black “ghost dog” appeared to her because she had turned a corner on her road to healing. Why do you think the dog appears to Pauline and Hattie at that particular moment in France? Do you think reuniting with Mies would have healed Hattie in the same way that reuniting with Pauline did?
  8. Compile your own breakup playlist. Bonus points if you can sing every syllable at the top of your lungs while crying in your car at a stoplight.