My only guesses are that Ron liked "stronger" women that were older, and maybe he thought Ann was out of his age bracket, or they didn't click personality-wise? But Ann is very attractive, and if she considered dating the man-child that is Tom Haverford, why not Ron Swanson? He's very appealing and stable. I find it hard to believe there wasn't sexual chemistry/tension there. It's not really that odd of a pairing if you think about it.
shareAnn never dated men who (appeared) as old as Ron. Sure, Rob Lowe is actually older than Nick Offerman, but he looks and acts much younger. Plus, Ann likes more conventionally attractive men. I do NOT find Tom Haverford attractive, but he's cute in an impish way.
shareRon likes strong, independent, emotionally detached woman which Ann was definitely not. I could see it happening towards the end of the series where they had grown, Ann more secure, Ron more open, but by then they were both in relationships.
"I'm doing good in the game, so I'm doing good in life!" - Charlie Kelly
I liked the sub-plot where they were fixing stuff at a house party.
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