Ann and Tom
One problem with ‘Parks and Recreation’ is that they never really knew what to do with Ann Perkins. She got paired up with multiple men, even when the decision didn’t seem to make a lot of sense.
Source: The Loop
Tom relentlessly tried to get Ann to date him, and when the two got together, it felt a little, um, gross. They weren’t well-matched as a couple and it felt somewhat out of character for her. They didn’t last long as a couple, but their entire relationship was kind of cringe-worthy.