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The episode begins with Jonathan meeting his ex-girlfriend, Suzanne, in a coffee shop when he gets a call from another potential client. He agrees to meet with his new client later on at a bar. Ray enters making Suzanne feel uncomfortable, so she leaves.
That night, Jonathan goes to the bar to meet his new client, Jennifer. She believes that her boyfriend, Gary, is cheating on her. He orders a white wine and at first she orders a water; only to change it later to a vodka martini. They share a common similarity that their significant others believe that they are alcoholics. Jennifer is quite impatient and explains to Jonathan how important it is to her for him to find out if her accusations are true and gives him a picture of her boyfriend.
The next day Jonathan is at a colonic cleansing center with Ray. Ray’s girlfriend booked him an appointment because she believes that he is filled with toxins. Jonathan reveals to Ray his secret new career – moonlighting as a private detective. Ray warns him that he is crazy to do this – that he has no professional experience and that it will all blow up in his face. Jonathan disagrees and really believes he has the ability to help people.
Later on that day, Jonathan is on the tail of Jennifer’s boyfriend. He follows Gary to a drug store and to the gym. Here Jonathan tries to strike up a conversation to find out if he in fact is a cheater. Both avenues lead to no avail. The client’s boyfriend’s last stop is at a church. Jonathan asks a stranger outside the church what was going on inside and finds out it is an Al-anon support group meeting.
Seeing that he has time to kill, Jonathan rushes over to George’s house. He finds George in a frantic panic. George has a huge herpes infection above his upper lip. George asks Jonathan to hit him hard on the infection so it draws less attention to the herpes and makes it look like he was attacked. As hesitant and Jonathan is, he whacks George in the face, only to get kicked in the cock by George’s self defense reaction.
Jonathan rushes back to the Al-anon meeting just in time to see the client’s boyfriend walk out of the church with Suzanne! He follows them to a local diner where he confronts them for making out (this never happened). Jonathan can’t realize that his relationship with Suzanne is over and as he begs for more time and understanding, he gets knocked out by Gary.
Jonathan meets back up with Jennifer where he reassures her of her boyfriend’s fidelity. So overcome with happiness Jennifer goes to answer her boyfriend’s call. Jonathan takes this as his cue to leave.
The next day, Jonathan and Ray are back at the colonic cleansing center to get Jonathan’s colon cleansed. Ray gives him the infamous, I told you so line.