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However, by the end of the pilot episode, he is kicked out of the group before being asked to join back in.After Britta definitively rejects his advances, Jeff begins flirting with his statistics professor, Michelle Slater, and they eventually begin dating.It becomes apparent that several members of the group rely on him playing this patriarchal role, though Pierce Hawthorne, as an elder male and the most sociopathic member of the group, naturally resists and tends to insult Jeff whenever he can, despite Pierce's lack of wit.Yet in episode "Spanish 101," Jeff develops a detente with Pierce.After a successful case in which he defended a stripper named Mysti, the Colorado Bar Association began scrutinizing his background.His rival and friend Alan Connor then betrayed him by sending the CBA an incriminating email, revealing that Jeff did not receive a bachelor's degree from Columbia University but, in fact, got one that was "less than legitimate" and "better than real" from the country of Colombia.Before this, he shares a number of UST-y moments with another study group member, Annie, after she kisses him to win a championship debate.After Professor Slater breaks up with him, he sleeps with Britta in the study room after a paintball fight in "Modern Warfare." At the end of season one, Britta and a newly interested Professor Slater compete for his affections, culminating in Britta professing her love for him at the school's "Tranny Dance" in "Pascal's Triangle Revisited." Soon after, he meets Annie outside and they kiss.
In addition, in one of the timelines of "Remedial Chaos Theory," Pierce brings up the subject of Jeff's father, which Jeff immediately evades.For over six years, he specialized in juvenile and traffic offenses, as well as DUI/DWA/DUID cases.During this period, in 2002 he successfully defended Ian Duncan from a DUI by comparing his accuser to 9/11, and they developed a friendship.At the beginning of season two, Britta recants her declaration of love for Jeff, saying she was caught up in the spirit of competition, and he comes to an uneasy understanding with both Britta and Annie.Later in the season, the study group finds out that Britta and Jeff had been hooking up in secret throughout the year, and both of them then realize they have no interest in continuing to hook up.