This reading group guide for The Last Blind Date includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Linda Yellin. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Topics & Questions for Discussion

1. A big theme in The Last Blind Date is the uprooting of one’s life—starting over. What does it take to start over? Courage? An adventurous spirit? Desperation? Think about people you know who have uprooted themselves. How do their stories end?

2. Linda waits over two years to meet Randy’s children. Do you agree with his decision not to introduce his children to women he dated? What do you think his reasoning was? Do you agree with his decision to not introduce his children to Linda for so long?

3. When Linda is worried that Randy won’t make a commitment to her, she’s told by a coworker who always speaks in sports metaphors that “Michael Jordan was famous for never thinking about the last game, only focusing on the next one, and how [she] shouldn’t dump former losses onto some guy who had just shown up at halftime.” Is that good advice? Was it relevant to Linda’s situation? Have you ever been wary of a current relationship because of problems in a past relationship?

4. Linda writes, “I used to share every detail of my life with Claudia and now most of my confidences were shared with Randy. You can’t be married to a man and reporting the intimate details of your life to a girlfriend, so as much as we adored each other, the distance between Claudia and me had grown wider than a plane ride.” Do relationships change when a close friend falls in love or gets married? In many ways, Linda and Claudia are quite different from one another. What is the glue that holds their friendship together? Why do you think Linda’s friendship with Claudia survived her move to New York when several of her other girlfriends drifted away? Are there quirky, unexpected friendships in your life? What are they based upon?

5. In the chapter “Dating for Girlfriends,” Linda explores the complexity of making new friends; the feelings associated with missing long-term girlfriends; and the importance of female friendships. She’s told that a potential friend “doesn’t even have time for the girlfriends she already has.” Is it more difficult to make friends later in life?

6. Before Linda meets Randy’s children, she asks for advice from two friends who were both second wives and stepmom experts. She’s told, “Whatever you do, never get between a little girl and her daddy.” And that she must “accept the fact that a man will always put his kids first.” Do you agree with that advice? Did you ever have to adjust to stepchildren? A stepparent? What was it like the first time you met them? Were you ever jealous of their relationship with your partner or your parent? How did you feel about Randy asking Linda to “throw the game” when Phoebe and Benjamin get upset that she’s winning at bowling?

7. How does Linda’s relationship with Phoebe evolve? Did it seem to be more challenging than her relationship with Benjamin? Why? Do you think it’s more difficult for girls to accept a new stepmom than it is for boys? How much did the kids’ ages at the time they met Linda factor into their acceptance of her? Did Randy do a good job of maintaining a balance between his relationships with his children and his new wife?

8. Linda is often intimidated by Randy’s ex-wife. The night before she first meets Phoebe and Benjamin, Randy’s mother tells her “what an excellent mother Susan was, how she was always volunteering for school trips, making organic meals, sewing costumes for school plays.” When Linda attends Benjamin’s baseball game she observes, “Susan said several hellos. She knew everyone’s name. I envied her being the real mother, the involved mother, the Snack Mother.” When introduced to another mom, Linda writes, “The fact that Susan and I looked like sisters only complicated matters.” What did you think of the relationship between Linda and Susan? Is it atypical? How did you feel about Linda trying to fix Susan up on a blind date? Do you think it is unusual that Randy married two women who looked a lot alike? Do you know anyone who’s also done that?

9. How did you feel about the relationships between Randy’s parents, Larry and Ruth? And Linda’s parents, Bernie and Vivien? How, in different ways, do they exemplify good marriages? Do you think that children of good marriages tend to end up in a good marriage? What did you think about the ways Randy and Linda interact with their parents? Consider Linda’s phone calls with her parents and the visit to the retirement home in your discussion. 

10. When Linda goes back to Chicago for a visit after settling in New York, she wonders, “Was I a Chicagoan living in New York? Or a New Yorker from Chicago?” How long does it take to feel truly at home in a new location? By the end of the book, do you think Linda considered herself “a New Yorker”?

11. After Claudia’s wedding, on the plane home to New York, Linda realizes she’s “learned that relying on Randy was a sign of strength, not weakness. After Teddy died, I’d pressed the hold button on my emotions. Randy taught me to trust again, to have faith . . . giving love was one thing. Accepting love, that was the real challenge.” Do you agree that accepting love can be more difficult than giving love? What are some of the other things that Linda learned throughout the course of her story?
 
Enhance Your Book Club

1. Visit the author’s website at http://lindayellin.com. It includes a timeline and pictures of her life, some of her magazine pieces, and a Q&A with Linda.

2. Have a movie night renting some good old-fashioned New York love stories, such as An Affair to Remember; Working Girl; When Harry Met Sally; West Side Story; You’ve Got Mail.

3. Linda writes about the numerous benches bearing dedications in Central Park and of Randy’s enthusiasm for the park’s history. Learn more about Central Park at: http://www.centralpark.com/guide/history.html. To find out how to get a personal plaque on one of the park’s benches, go to: http://www.centralparknyc.org/donate/honor-someonespecial/adopt-a-bench.html.

4. The next time you’re in New York, visit Randy’s bench. It’s just south of Poets Walk, “right behind the butt of Columbus.”