. ▁Bobby ▁is ▁also ▁a ▁recover ing ▁g amb ling ▁add ict , ▁and ▁still ▁att ends ▁G amb lers ' ▁An onymous . ▁However , ▁only ▁Jack ▁knows ▁about ▁this , ▁as ▁it ▁could ▁effectively ▁mean ▁the ▁end ▁of ▁Bobby ' s ▁career ▁with ▁the ▁F BI ; ▁Bobby ▁experienced ▁a ▁re lapse ▁in ▁" The ▁G amb ler ", ▁when ▁an ▁under cover ▁operation ▁required ▁him ▁to ▁in fil tr ate ▁a ▁pok er ▁game ▁to ▁capture ▁a ▁not orious ▁criminal , ▁but ▁after ▁he ▁lost ▁most ▁of ▁the ▁money ▁don ated ▁by ▁the ▁F BI ▁in ▁a ▁game ▁outside ▁the ▁official ▁match , ▁he ▁played ▁one ▁final ▁game ▁with ▁the ▁crim inals ▁he ▁had ▁been ▁in fil tr ating ▁to ▁win ▁back ▁the ▁money ▁and ▁then ▁called ▁the ▁operation ▁off . ▁From ▁the ▁first ▁season , ▁Bobby ▁dated ▁Dar cy ▁D ' Ang elo ▁( Pol ly ▁Sh annon ), ▁a ▁journalist ▁who ▁initially ▁wrote ▁a ▁very ▁sc ath ing ▁story ▁on ▁the ▁F BI ▁before ▁Bobby ' s ▁genu in ely ▁emot ional ▁appeal ▁won ▁over ▁her ▁c yn ical ▁point ▁of ▁view , ▁but ▁the ▁two ▁broke ▁up ▁in ▁the ▁third ▁season ▁when ▁Dar cy ▁accepted ▁an ▁offer ▁of ▁a ▁high - profile ▁job ▁in ▁Los ▁Angeles . ▁Short ly ▁after ▁this , ▁he ▁and ▁T ara ▁discover ▁a ▁mut ual ▁att raction , ▁and ▁they ▁eventually ▁kiss ▁in ▁the ▁episode ▁" T roy ▁Story ", ▁although ▁they ▁decide ▁not ▁to ▁follow ▁it ▁up ▁at ▁the ▁time .