Carrie struggles with what she should write about in her essay.Weaver encourages her to write about what she fears the most but when Carrie decides to write about sex, Weaver tries to help her figure out something better and just ends up getting in the way.Walt takes drastic measures to keep himself safe when Bennet moves to a dangerous neighborhood.Also, Larissa and Samantha plan to have a threesome with Harlan.
When Sebastian learns that his mother is getting remarried, he asks Carrie's dad, Tom, for help to make sure she is legally protected.Carrie declines going with Walt, Sebastian, and Donna and instead goes to her regular hangout where, due to a combination of bad luck and carelessness, her valued purse gets stolen.She later has a chance meeting with Samantha who agrees to help her out of being locked out of her apartment.Sebastian also deals with his estranged father who comes back into town, but is more interested in business then father-son bonding.Elsewhere, Tom invites his girlfriend, Deb, to spend the weekend with him, which doesn't go exactly as planned.
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Carrie has been living at Larissa's apartment in Manhattan for the past three or four weeks of the summer with Walt as her platonic roommate.With Larissa still out of the country, Carrie has been filling in for her at Interview magazine full-time during the day and partying at local nightclubs at night.Meanwhile, Samantha and Mouse meet and Samantha wastes no time giving Mouse sex tips over how to "go at it" with West. Back in Castlebury, Sebastian and Maggie run into each other after three months apart.She has not seen or spoken to either Sebastian or Maggie since their falling out.
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But by chance during the Fourth of July weekend, Carrie runs into Sebastian when he tags along with Donna to the city to meet Donna's cousin Samantha Jones, an older woman in her early 20s, who co-manages a rock music nightclub.Elsewhere, Tom finds out about Dorrit dating Miller and wants to meet him.Dorrit tries to prevent her father from meeting Miller fearing that Tom may find out that she and Miller are in a sexual relationship and that they both take recreational drugs.Maggie and Sebastian start to grow closer as Maggie discovers some shocking news, she's pregnant.Meanwhile, Mouse is apprehensive about applying to safety schools but West thinks it's good to be on the safe side.