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Charlie went on a date with Jackie after meeting her online.
After Mac and Dennis set up an online dating profile for Charlie, they set up a date with Jackie. Charlie was extremely nervous so he was sweating through his shirt and he stuttered some of his words, calling his made up philanthropist profession a "full on rapist". When Dennis and Mac tried to swoop in to help, they only made her more uncomfortable and she left. ("The Waitress is Getting Married")