Cocktails (Season 3, Episode 17)
With an invitation to the house of the CFO, Jim brings along Karen as his date to his first company gathering since his promotion. In the midst of all the “fun,” Karen points out a guy at the party to Jim who she used to date. Later, after talking with a couple, she makes mention that she saw the man while they were separated. Karen adjusts the tie of another former boyfriend while Jim looks on. After being invited to shoot hoops with CFO David Wallace, Karen makes sure to tell Jim not to say anything about their relationship; for he might still have feelings for her.
The first guy, Jim doesn’t make much of anything of, but the second guy, Jim is more quizzical than anything else. The third guy, Jim looks more astounded than mad, but as she remarks to him about her past with David, Jim is finally broken and asks if she has dated everyone at the party. Karen finally breaks and admits that she wasn’t serious. She says she didn’t date any of them and that Jim is actually her first. Jim is amazed, and Karen breaks again and admits that it’s just too easy.
8 – There has been plenty of speculation on what Karen’s intention was here. Some say she was testing Jim’s jealousy. Some say she wanted to see if Jim would get fed up and break up with her. Personally, I see this as a test to see if Jim cared enough about Karen to bring up her past right away or until it got to ridiculous proportions. If that was her intention, she succeeded in getting almost no reaction after each guy. Jim was unfazed…perhaps pining for another?
8 – I think Karen really did date the first guy, but she saw the lack of Jim’s reaction and wanted to see how far she could go. She pointed out four additional guys, just at the party, that she has dated before Jim speaks up. Extra point for the extra little mini-prank right at the end, just to rub salt on the wound.
Double Dose Award – This is the second (and third) time Karen has pranked Jim since they have worked together. Karen gets the rare double prank in one swoop on the one man who pranks everyone else.
Taste of Your Own Medicine – The king of all pranks gets some of the business from Karen, twice in one night. It’s so easy, it’s not even fun.