The Boyfriend Chapter 14 Summary & Analysis
⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.
Summary
Late at night in Sydney’s apartment, she and Gretchen are drinking wine and crying over Bonnie’s murder. They have gone through a whole box of tissues and a bottle of wine. Gretchen shares a memory of Bonnie practicing different smiles in front of a mirror—a happy smile, a client-impressing smile, a silly smile—so she would never look “weird” to others. The conversation turns to how Bonnie kept her romantic life secret, never revealing Dr. McHottie’s name or introducing him to her friends, which frustrates Sydney because that secrecy may have allowed the killer to remain unknown.
Gretchen pulls out two scrunchies Bonnie left at her apartment, and both women wear them in Bonnie’s honor. They toast to Bonnie and finish the wine. Gretchen decides to spend the night at her boyfriend Randy’s apartment, noting that Randy handled the discovery of Bonnie’s body with surprising calm. Sydney walks Gretchen to the door and then is left alone.
Feeling isolated and lonely, Sydney searches for comfort food and finds a pint of mint chocolate chip ice cream that Bonnie had brought over. Sydney hates that flavor, but she eats it anyway as another tribute to her friend. While eating, she picks up her phone and opens the Cynch dating app. This time she types a specific name into the search bar: Jacob Sousa. And she finds him.
Key Events
- Sydney and Gretchen share an emotional evening, reminiscing about Bonnie.
- Gretchen reveals that Bonnie practiced multiple smiles for different social situations.
- The women discuss Bonnie’s refusal to share details about her boyfriend, Dr. McHottie.
- They wear Bonnie’s scrunchies and toast to her memory.
- Gretchen leaves to stay at Randy’s place; Sydney is left alone.
- Sydney eats mint chocolate chip ice cream (a flavor she dislikes) as a tribute.
- Sydney opens the Cynch app and searches for “Jacob Sousa” — and finds his profile.
Character Development
Sydney is shown in a raw, vulnerable state. She grieves openly and admits she does not want to be alone, which contrasts with her earlier appreciation for solitude. Her determination to honor Bonnie through the scrunchie and ice cream shows her loyalty and need for ritual. Most importantly, her decision to search for Jacob Sousa on Cynch marks a shift from passive victimhood to active investigation, even if she is not yet sure what she is looking for.
Gretchen emerges as a supportive friend who uses shared memories and small keepsakes (the scrunchies) to cope. Her mention of Randy’s unflappable reaction to the dead body hints that Randy may either be unusually strong or unnervingly detached—a thread that might matter later.
Bonnie is further characterized through her friends’ memories: she was meticulous about her social presentation to the point of practicing smiles, yet she was also secretive about her romantic life. This contradiction deepens the mystery around her murder.
Themes, Symbols, or Motifs
Performance of self. Bonnie’s habit of practicing different smiles suggests she carefully curated how others saw her. This raises questions about whether the “real” Bonnie was ever fully visible to her friends—and whether the killer saw through that performance.
Memorial objects. The scrunchies and the unwanted ice cream become physical tokens of remembrance. Sydney’s willingness to wear and eat things she dislikes shows how grief can transform the meaning of ordinary objects.
Technology as a dangerous tool. The Cynch app, which was previously used to find anonymous dates, is now repurposed by Sydney as a search engine for a specific name. The app’s ability to locate Jacob Sousa underscores how digital platforms that promise connection can also expose people to risk.
Why This Chapter Matters
Chapter 14 is a quiet but pivotal interlude. It deepens Bonnie’s character while also providing Sydney with her first concrete lead: the name Jacob Sousa. The chapter also contrasts the warmth of female friendship with the cold absence left by murder, and it plants suspicion around Randy’s composure. By ending on Sydney finding Sousa’s profile, the chapter propels the investigation forward and raises the stakes for the next scene.
Study Questions & Answers
1. Why does Sydney decide to search for Jacob Sousa on the Cynch app?
Sydney remembers that Bonnie was dating a man named Jacob Sousa, but Bonnie never introduced him or even showed his photo. Now that Bonnie is dead, Sydney wants to find out more about this mysterious boyfriend, suspecting he may be the killer.
2. What does Gretchen’s story about Bonnie’s practiced smiles reveal about Bonnie?
It shows that Bonnie was socially anxious and methodically managed her image. She had different smiles for different contexts, which suggests a calculated approach to relationships—and possibly a hidden side she kept from even her closest friends.
3. How does the ice cream scene contribute to the chapter’s mood?
The mint chocolate chip ice cream is a flavor Sydney dislikes, but she eats it because Bonnie brought it. This small, unpleasant act of devotion captures Sydney’s grief and her need to connect with Bonnie’s memory, reinforcing the chapter’s themes of ritual and loss.