▁ ▁H . ▁Jon ▁Benjamin ▁as ▁Keith , ▁Or lo ff ' s ▁G ulf ▁War ▁veter an ▁friend ▁ ▁Amy ▁Po eh ler ▁as ▁Pat ty , ▁Or lo ff ' s ▁co - dependent ▁stri pper ▁friend ▁ ▁Kim ▁Ra ver ▁as ▁K ash ia , ▁Or lo ff ' s ▁girl friend ▁ ▁Matt ▁B esser ▁as ▁Ron , ▁Martin ' s ▁b oss ▁ ▁Les ▁Mau ▁as ▁Mr . ▁Chan , ▁a ▁client ▁of ▁Martin ' s ▁ ▁David ▁Cross ▁as ▁Don ▁Wass ermann ▁ ▁K atie ▁Roberts ▁as ▁Don na ▁ ▁Sal ▁E . ▁Gra z iano ▁as ▁Jim bo , ▁Pat ty ' s ▁ex - boy friend ▁ ▁Mary lou ise ▁Bur ke ▁as ▁Mrs . ▁Fl am ▁ ▁Mi ri am ▁Tol an ▁as ▁L inda ▁ ▁Ted dy ▁Col uca ▁as ▁Pet ros ▁ ▁Re ception ▁Met ac rit ic ▁assigned ▁a ▁score ▁of ▁ 4 8 ▁out ▁of ▁ 1 0 0 ▁based ▁on ▁ 1 1 ▁critics , ▁indicating ▁" m ixed ▁or ▁average ▁reviews ." ▁ ▁Acc ol ades ▁The ▁film ▁has ▁won ▁numerous ▁awards ▁including : ▁Texas ▁Ch ains aw ▁Mass acre ▁Film ▁Festival ▁( W inner : ▁Director ’ s ▁Prize ) ▁Sar as ota ▁Film ▁Festival ▁( ▁“ Best ▁of ▁Fest ” ▁Award ) ▁East ▁L ans ing ▁Film ▁Festival ▁( W inner : ▁A udi ence ▁Award : ▁Best ▁Fe ature ) ▁The ▁Art ▁Institute ▁of ▁Chicago ▁( W inner : ▁Christopher ▁W etz el ▁Award ▁for