In an effort to transition from intern to writer, Carrie begins pitching article ideas to Larissa. Larissa agrees that if she can secure an interview with Adam Weaver, who is infamous for his privacy, she'll publish her as a writer. Carrie meets Weaver when attending his play with Bennet. During an act depicting his brother's funeral, Carrie finds herself unable to contain her laughter, drawing negative attention to her from the audience. After the play, Bennet warns her that her inappropriate display will get her "banished to Siberia", but they're both surprised when Weaver approaches Carrie and thank her for laughing. He explains that the scene is intended to be funny, but that most people don't understand thehumor His manager has advised him to alter it, but Carrie encourages him not to and regales him with a story from her mother's funeral. When she tells him she works for Interview and is interested in talking to him more, he asks her to join him for a drink.
At first, Weaver is reluctant to share anything personal, but he erects a deal with Carrie to open up if she does. After admitting - off the record - that his brother's funeral was even darker than shown in his play, he and Carrie share a kiss.
Worried that she crossed a line, Carrie calls Larissa and tells her what happened. Instead of being chastised, Larissa commends her for her committment to the story. She tells Carrie that she'll be extremely imressed if she can use her relationship to reveal further information about Weaver, but reminds her to make sure he's on the record this time. However, Carrie is hesitant about using Weaver.
The next time Carrie and Weaver meet up, he shares that his dad punched him for laughing at his brother's funeral and that they haven't spoken since. Carrie is very empathetic because she feels that her own family leaned on one another after her mother's death. Once again, Carrie and Weaver kiss.
At work, Carrie tells Larissa that she wants to drop the story on Weaver. Larissa misunderstands and assumes that Carrie was unable to get a decent scoop, but Carrie corrects her. She says that while she unearthed quite a bit regarding Weaver's life and work, she isn't comfortable exploiting him or their relationship. Larissa then dismissively orders Carrie to get her coffee. It's clear that Larissa is disappointed in her, but Carrie is happy with her decision.
In Too Close for Comfort, Carrie gleans that Weaver is writing a play about his ex-girlfriend. Carrie becomes nervous that he's still in love with his ex and that their relationship will eventually be relegated to a rebound.
Later, when Sebastian is at the Bradshaw household talking to Carrie's dad, she receives a phonecall from Weaver. Carrie frantically lies and tells both Sebastian and her dad that Weaver is just a friend from work. She begins to question whether she can maintain a friendship with her own ex while still dating Weaver.
When Carrie learns that Sebastian's mom is marrying her young fitness instructor - sans prenup - , she volunteers to support Sebastian at the wedding. However, the date of the ceremony conflicts with her plans to spend the day with Weaver. She resolves not to cancel on either boy, aware that it will be difficult to be there for both of them.
On her date with Weaver, Carrie bluntly asks if he's still in love with his ex. Weaver is amused as he laughs and tells her that his ex is a "crazy bitch". Carrie is relieved until Weaver tells her that he thinks staying friends with an ex can cause problems. Before Carrie can contemplate telling him about Sebastian, it suddenly starts to rain.
Luckily, Weaver's parents home is nearby. They decide to rest there until the storm passes. While Carrie is changing into dry clothes, she asks Weaver to retrive a snack from her purse. When she returns from the bathroom, she finds him reading her journal. The two briefly argue, but Weaver placates Carrie by insisting that he's never done anything so invasive before. He apologizes profusely and tells her that he was overcome by wanting to know everything about her because he likes her so much. Carrie is still upset, but seems to forgive him. Weaver then tells her that, evident by what he's read, they have a lot to talk about. Carrie assumes he's refering to Sebastian, but as she begins to explain, he tells her that she should have told him she was a virgin. Carrie tells him that she didn't want to make a big deal out of it because that adversely affected her last relationship. Weaver assures her that having sex for the first time is a big deal and that he would want her to be comfortable talking to him about it. Carrie then kisses him and tells him she's ready to have sex.
Post-coitus, Carrie and Weaver joke about getting married. When Weaver teases that the chapel will be closing soon, Carrie remembers that she was supposed to go to Sebastian's mom's wedding. After she misses her train, she calls Mouse (off-screen) and asks her to fill in for her. She then decides to be honest with Weaver. She tells him about Sebastian and their plans for the evening. He's grateful that Carrie was honest with him, especially after she tells him that she's glad she missed her train.