Chapter Twenty: Will – The First Real Date
⚠️ 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
Chapter Twenty is told from Will’s perspective. After Charlie (Charlotte’s app persona) suggests meeting for a drink, Will and Beckett drive more than an hour to a Boston‑suburb sports bar. Will warns Beckett not to push Charlotte too hard because she seems embarrassed by the situation. At the bar, Charlotte is visibly nervous – her hands tremble and she keeps looking around. She orders a gin and tonic for courage. The conversation is awkward at first; Charlotte admits it feels “weird.” Beckett teases her but also reassures her that she can ask whatever she wants. They discuss their past relationships: Charlotte reveals that her ex-boyfriend Mitch is the possessive guy from class, and they broke up due to a “mismatch of libidos” (she wants sex at least once a day). Beckett and Will are both intrigued. When Charlotte takes off her white sweater, Beckett points out the contrast between “Charlotte” (the studious, prim STEM student) and “Charlie” (the confident, sexual woman on the app). The air grows charged as Charlotte admits she wants to kiss both of them. Beckett leans in and says, “If you want to be kissed, Charlie, all you have to do is ask.”
Key Events
- Will receives Charlie’s text agreeing to a drink at a bar near Boston; he and Beckett drive there together.
- Will advises Beckett not to overwhelm Charlotte, acknowledging her skittishness.
- At the bar, Charlotte is tense, orders a gin and tonic, and blurts out that the situation feels weird.
- Beckett openly challenges her to ask what she really wants, and she gradually relaxes.
- Charlotte explains that her ex Mitch became controlling after their breakup; the real reason for the split was a libido mismatch – she likes sex at least once a day.
- Beckett and Will confirm they have never hooked up with each other, and Will admits he has only ever been with women.
- Charlotte removes her white cardigan, and Beckett calls out the duality: prim “Charlotte” vs. confident “Charlie.”
- The conversation turns to double penetration; Charlotte asks if they’ve done it or want to, and Will says he sometimes is into it but doesn’t plan sex.
- Charlotte confesses she wants to kiss both of them (not at the same time), and Beckett replies with the invitation: “all you have to do is ask.”
Character Development
- Will – We see his observant, protective side. He cares about Charlotte’s comfort and warns Beckett not to push. He also reveals his own shame about “extra flavors of sex” and his journey toward accepting that his desires are not shameful. He reaches out to hold Charlotte’s hand to steady her, showing a gentle, patient approach.
- Beckett – He is the provocateur, teasing Charlotte to draw out her Charlie side. But he also shows a softer moment when Charlotte mentions his high‑school ex (Shannon) – he tenses up, hinting at unresolved hurt. His philosophy (“do what feels good”) contrasts with Charlotte’s need for control.
- Charlotte/Charlie – This chapter deepens the split between her personas. In class she is the proper, high‑achieving “Charlotte”; here she is the sexually curious “Charlie.” Her nervousness suggests she is ashamed of wanting this, but she slowly owns it, asking direct questions about DP and kissing. Her admission that her ex couldn’t keep up with her sex drive is a vulnerable moment.
Themes, Symbols, or Motifs
- Dual Identities – The central theme of the chapter. Beckett explicitly names the two sides: the white‑sweater‑wearing overachiever (Charlotte) versus the “tits practically hanging out” woman (Charlie). This duality is not seen as a flaw but as “hot.” Charlotte herself says people have layers, and Will acknowledges they do too.
- Shame and Empowerment – Will reflects on his own shame about wanting non‑vanilla sex, and Charlotte’s embarrassment about being on a date with two guys. The chapter argues that if all parties consent, there is nothing shameful.
- Communication and Consent – Will repeats “It’s just a drink, no expectations.” Charlotte is encouraged to ask whatever she wants. Beckett’s final line – “all you have to do is ask” – reinforces that explicit communication is the path forward.
- Past Scars – Both Beckett and Charlotte carry baggage from previous relationships (Shannon’s infidelity, Mitch’s possessiveness and libido mismatch). These histories colour their current interactions.
Why This Chapter Matters
Chapter Twenty is the first in‑person meeting where the trio move from app‑based flirting to real‑world chemistry. It establishes the emotional and sexual boundaries: Will is the steady hand, Beckett is the playful challenger, and Charlotte/Charlie is learning to voice her desires without shame. The chapter also hints at Beckett’s vulnerability (the ex‑girlfriend wound) and sets up the critical moment when Charlotte must decide whether to take the next step. The stage is now set for a potential threesome, but the characters still have personal hurdles to overcome.
Study Questions and Answers
1. Why does Will tell Beckett not to push Charlotte too hard?
Will senses that Charlotte feels embarrassed about wanting two guys. He believes she needs to feel safe and not pressured, so he asks Beckett to tone down his usual flirtatiousness. This shows Will’s protective nature and his understanding of her vulnerability.
2. How does the chapter use the “Charlotte vs. Charlie” contrast to develop the theme of identity?
Beckett describes Charlotte as the prim, studious girl in cashmere and pleats, while Charlie is the confident, sexually open woman who would wear a tank top as a top. Charlotte herself acknowledges having layers, and the men find the duality attractive. The chapter suggests that a person can contain multiple selves without being fake.
3. What does Charlotte’s revelation about her libido reveal about her past relationship?
She reveals that her ex Mitch couldn’t match her desire for sex at least once a day. This explains why Mitch acted possessive in class – he may still be threatened by her sexuality. It also shows that Charlotte’s sexual appetite is a core part of her that she is no longer willing to hide, leading her to seek partners (two at once) who can meet her needs.