According to Jim Recap: The Pass
Jim has found himself a new employer, one who he used to go to high school with, and unfortunately his new employer is also the guy in school that always had the best of everything, and never had any problem telling everyone else about it. Well now Jim can turn the tables because it seems that he has something that the other guy wants. It's too bad that what the other guy wants is Cheryl.
One night when they go out to dinner to discuss plans for working together, Jim takes a call on his cell phone (he didn't get a real call - he had Andy call him to make him seem important) and leaves the table. When they get home later that night, Cheryl tells Jim about what happened, and it's safe to say that he doesn't have the reaction she wants - he is excited that he's finally got the upper hand with something. That doesn't help.
When they invite him over for dinner the next night, Jim tries to rub it in his face, and that just gets Cheryl mad, which makes things worse. Lucky for Jim he does realize it before things get too bad, and he even defends Cheryl, albeit somewhat weakly, and he even gets a punch in for her benefit - but she knew that he knew she was watching, so it doesn't really count.
He even gets to keep the job - that may or may not be because he sets the guy up with Dana, but it is really a win-win scenario for Jim either way.
