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On November 5, 2007, Showtime ordered 13 new episodes for a fourth season of Weeds. It started on Monday, June 16, 2008 and concluded on Monday, September 15, 2008. The season opener "Mother Thinks the Birds are After Her" was the last episode with "Little Boxes" as the theme song. The opening credits of subsequent episodes, after a recap of previous episodes, begin with a video title card unique to each episode. For the second episode of the season, for example, a highway sign reads "Weeds -- Created by Jenji Kohan" — the embedded text used for all title cards since the show's inception. Each title card also has a prop or part of the setting that refers to a plot element in the episode. Some part of the title card morphs into a marijuana leaf. In the highway sign example, a downward arrow designating a lane becomes a slightly larger pot leaf. Silas and Shane are aged 17 and 13 respectively. However, Silas turns 18 at the end of the season.
Nancy has relocated to the border in search of a new life but she soon finds her past to be inescapable. Both problems and people follow her on her journey, but some have finally been left behind.
After settling her family in Ren Mar, Nancy turns her attention back to business. Later, Guillermo gives her a much-needed crash course in "running" across the border. Meanwhile, Celia gets further acquainted with life in prison. Lenny leaves Silas and Shane to care for Bubbie while he goes to the track. When Lenny returns, Andy confronts him about some family history.
Nancy makes her first successful smuggling run across the border with both drugs and human cargo. Meanwhile, Captain Till strikes a deal with Celia to get her out of jail. In return, she must gather evidence to incriminate Nancy and Guillermo. Back in Ren Mar, Andy tries to convince the family, including his father, to put Bubbie out of her misery.
After Bubbie's death, the entire Botwin family sits shiva (the Jewish period of mourning) for seven days. After shiva, Nancy is sent on a mission and takes Andy along with her. Now that shiva is over and Bubbie is gone, Lenny decides to sell the house. Meanwhile, Celia continues her flirtation with Captain Till, and Doug finds refuge with the Botwins.
Guillermo gives Nancy a new job and she soon finds working retail isn't as mundane as it appears on the surface. Celia's deal with Captain Till brings her dangerously close to the action. Meanwhile, having been left in the desert by Nancy, Andy finds himself with a pack of immigrants and a very unfriendly Coyote. Back at home, the boys battle an infestation of bees.
Nancy follows the tunnel in the back of the maternity shop and sees something she shouldn't at the other end. Dean takes a new job, leaving Isabelle to live with Celia. Meanwhile, Silas flirts with Lisa, and Doug falls in love with a vision of beauty who washes up on the beach.
When Nancy is denied a share of the incoming pot by Guillermo, she decides to go over his head to Esteban. Celia discovers the cheap medication at Mexican pharmacies. Silas and Lisa get intimate, while Shane discovers some shocking photos. Andy and Doug begin interviewing for their human smuggling operation.
A spontaneous date ends in near-violence for Nancy and Esteban; Silas reveals to Lisa that he grows pot, and she makes him a tempting offer; Andy and Doug smuggle their first customer across the border; Celia develops an addiction.
Despite their busy schedules, Nancy and Esteban try to find some time for each other. After finding out about Shane's fantasies and Silas's new and much older girlfriend, Nancy also has to talk to both of her sons. With their relationship going on, Lisa and Silas add some special offerings to her cheese shop.
Nancy learns that the tunnel is being used for more than drugs. Esteban puts her fears to rest as well as her nagging headache with a strong remedy. Celia's family stages an intervention in order to force her into rehab. Andy finds Maria and takes her across the border to an awaiting Doug. Silas babysits while Shane explores new territory with his two girlfriends.
Nancy must deal with the aftermath of Shane's exploits, her Ayahuasca trip, and more confrontation with Guillermo. Celia's struggles with her rehab partner, Barry, force her to find a new rehab facility. Doug and Maria's relationship quickly goes south and they both turn to Andy for help. Meanwhile, Silas's "sandwich" business has grown too big, forcing him to turn to Nancy for help.
A fed up Nancy squeals to the DEA to bust the tunnel while she plays it cool with Esteban. Embracing rehab, Celia sets out to make amends with her family. Andy succumbs to Maria's advances, and later comes clean to Doug. Shane impresses his girlfriends with his drug scoring abilities.
The DEA brings Nancy in for questioning and then she must explain things to Esteban. Celia travels deep into Mexico to make amends with estranged daughter Quinn. Meanwhile, Silas meets Lisa's ex-husband and Doug finds a reason to live. Nancy makes a shocking revelation to Esteban.
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