Parks and Rec may be about the parks department of Pawnee... but fans know that's just a fraction of what makes the show great, and it's the relationships (romantic and otherwise) that are the real heart and soul of the series. That said, not every romantic choice made on the series was one the audience could get behind. While some couples had everyone rooting for them from the start (like Ben and Leslie), even they occasionally made some bad choices.
And other relationships (like Tom and Mona Lisa) just had everyone rooting for them to end, and as fast as possible. But from individual dates to whole romantic connections, which decisions of the Parks and Rec characters were the most eyebrow-raising?
Ann Pursuing Mark
Ann, unfortunately, made a lot of questionable relationship decisions - and actively pursuing Mark was definitely one of them. It was clear from the start that Leslie had a huge crush on Mark, and it wasn't always an unrequited one, as they had hooked up in the past. Even though Mark was not interested, for Leslie's best friend to try and start something with him was always going to be awkward. And, of course, it didn't work out anyway.
Leslie's Scavenger Hunt With Ben
Leslie's enthusiasm and thoughtfulness is inspiring, but also a little terrifying - as Ben found out, when she created a massive and elaborate scavenger hunt for him that would reveal the location of their special date. Of course, Ben was terrified he wouldn't get all the clues, and enlisted Ron's help to get him there. This ended well, but Leslie's decision to turn something that should have been a fun evening into a source of so much work and stress for her partner just wasn't a good one.
Chris And Millicent Grinding
Another somewhat inappropriate connection to begin with was between Chris and Millicent Gergich - which was slightly awkward, as it meant that Jerry's daughter was dating his boss! However, this could have been fine (Chris and Jerry didn't work closely together, and Chris approached him about it ahead of time).
But Chris and Millicent definitely took things to an uncomfortable place at a Halloween party, where they decided to grind on each other right in front of Jerry. They were all adults, sure, but right in front of your father might not be the best place to dry hump on the dancefloor.
Ann And Andy
Pretty much everything about Ann and Andy's relationship dynamic was questionable, start to finish! From Ann's willingness to take care of everything for Andy, to his later obsession when they broke up - squatting in the pit and trying to lie to her to win her back, their time as a couple was just awful. Add in Ann's decision to kiss Andy in the hospital, and this was just a relationship made of red flags.
Ann Chasing Down Chris
Another situation that was all-round questionable was after Chris and Ann broke up... and he was just so darn nice about it that she didn't even realize! Instead of actually communicating with him openly (which is, admittedly, difficult given his over the top positivity), Ann sent Leslie on a mission to snoop in his house, and then stormed down there herself to confront him over 'cheating' on her, in front of their colleagues. All in all, this was just not handled well by anyone involved.
April & Andy Marrying So Quickly
This actually turned out e extremely well, with Andy and April making one of the cutest couples on the show, and becoming a great partnership and great parents in the end. However, fans were definitely wondering about the wisdom of these two getting married as quickly as they did, and 'surprising' everyone with a wedding at a housewarming! At first, most fans felt the same way Leslie did - that this was a terrible decision that should be stopped for the good of all involved... thankfully, Leslie, and everyone else, was wrong.
Ann's Fling With Kiley
After her breakup with Chris, Ann goes through an interesting time, personally. She dyes her hair bright colors, she struggles with a little soul searching... and she decides to make out with a patient while working in the medical tent at the Harvest Festival.
This is with Donna's encouragement, who sees the patient as a way for Ann to 'get over' Chris, but instead, she ends up hurting his feelings, too. Using a person to get over another person was never going to be a smart move.
Leslie And Ben Dating At Work
Much like Andy and April, this is a decision that may have been questionable, but fans were still rooting for it, because everyone loves Leslie and Ben. However, their decision to risk both of their careers in order to date at work, knowing it was against the rules, is the definition of a questionable one. Thankfully, this all worked out when Ben took the fall for them both, but it was still a risky move.
Tom Dating Mona Lisa
Tom makes quite a few less-than-brilliant relationship and dating decisions on the show, but his worst has to be his decision to date Mona Lisa. For one thing, she is his best friend's sister, which was just bound to get weird (especially given the siblings in question), but for another, she was a terrible person who just wanted him to buy her things. Later, she convinced her father that Tom had wronged her, which led to massive issues with his business, too.
Everything About Ron & Tammy (One And Two)
It's impossible to narrow this down, because Ron's questionable decisions when it comes to his first two wives are so painfully numerous. Essentially everything about these relationships was eyebrow-raisingly toxic, although it's certainly the most difficult to get the image of Ron in a robe, with cornrows, in jail, married to Tammy again, out of any fan's head. Ron and the Tammys are the definition of terrible romances, and there was barely a decision in these relationships that fans weren't left questioning.