Book #21: To Sir With Love, Lauren Layne

Love Is Blind meets You’ve Got Mail in this laugh-out-loud romantic comedy following two thirty-somethings who meet on a blind dating app—only to realize that their online chemistry is nothing compared to their offline rivalry.

Perpetually cheerful and eager to please, Gracie Cooper strives to make the best out of every situation. So when her father dies just months after a lung cancer diagnosis, she sets aside her dreams of pursuing her passion for art to take over his Midtown Manhattan champagne shop. She soon finds out that the store’s profit margins are being squeezed perilously tight, and complicating matters further, a giant corporation headed by the impossibly handsome, but irritatingly arrogant Sebastian Andrews is proposing a buyout. But Gracie can’t bear the thought of throwing away her father’s dream like she did her own.

Overwhelmed and not wanting to admit to her friends or family that she’s having second thoughts about the shop, Gracie seeks advice and solace from someone she’s never met—the faceless “Sir”, with whom she connected on a blind dating app where matches get to know each other through messages and common interests before exchanging real names or photos.

But although Gracie finds herself slowly falling for Sir online, she has no idea she’s already met him in real life…and they can’t stand each other.

Discussion Questions: 

At the start of the book, Gracie believes whole-heartedly in “fairy tale romance.” Do her Disney-esque expectations help or hinder her path towards finding a fulfilling relationship?

Gracie’s watercolor art starts as a side-business mostly ignored by her family, but ultimately blossoms into a career. Do you think she would have had the same success as an artist had she tried to “make a go of it” earlier in her life? Or, were the experiences that delayed her career (taking over the shop, supporting her father during his illness, etc) an important part of what made her the artist that she is?

Eventually, Gracie and her siblings decide to close Bubbles & More. Do you think this was inevitable given the changing times (e-commerce, bigger box stores, etc)? Or do you think Gracie could have saved it, had it been her passion the way it was her father’s? Did you respect Gracie more or less for following her own dreams instead of carrying on her father’s legacy?

Gracie eventually learns that her sister and brother-in-law’s “storybook romance” isn’t as perfect as she imagined it to be. How do you think her observation of a formerly happy couple experience “real world problems” influenced her perception of romantic relationships?

From Gracie (and the reader’s) perspective, Sebastian is fairly reserved throughout much of the story, especially compared to the more playful Sir. How do you think Sebastian viewed the difference between Gracie and “Lady”?  Do you think their coming to know two different sides of the other person ultimately enhanced their relationship, or did it simply delay their happy ending? 

To Sir With Love was written as a deliberate nod to Parfumerie, a Hungarian play from the 1930s that was also the inspiration for The Shop Around the Corner, In the Good Old Summertime, She Loves Me, and You've Got Mail. What do you think it is about the premise of two people falling in love over letters (and separately, in real life) that is so compelling to both creators and consumers?