A Date - You're the Worst
Dorothy and Edgar go out on a date on You're the Worst. "Side B*tch" is the sixth episode of the show's second season.

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FXX
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You're the Worst
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You're the Worst Season 2 Episode 6: "Side B*tch"
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You're the Worst Season 2 Episode 6 Quotes

Hm. Maybe I should be more direct. I mean with Lindsay, I got friend-zoned for life. One time she texted me, "Yo girl, wanna get brunch?"

Edgar

Edgar: You mean just ask [Dorothy] out?
Jimmy: No, get her hammered and finger-bang her in your car.