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* Nathan having fun with a friend he found on Craigslist in "Fun" to prove that he's a fun guy. After duping the dude into giving his blood and urine to measure his serotonin, Nathan decides to go to an amusement park with him and they both have a lot of fun.
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** The pair bond even further in "The Movement" when Nathan hires him to track Jack Garbarino and the pair talk about how to move on from divorce. Becomes even more heartwarming when you realize that Nathan brought up his own real-life divorce off-camera and that Wolfe is responding to him.
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* Nathan and Angel sharing a pizza after a [[{{Jerkass}} particularly rude customer]] decided not to pay for it.
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* As possibly misguided as it is, Nathan's inclusive defense of his plan to [[ItMakesSenseInContext use balloons to help overweight people ride horses]]:
--->'''Nathan:''' I disagree. I think anyone should be able to do anything.
* "Nathan for You: A Celebration" features Nathan revisiting a handful of his past clients. Brian, who's been consistently condescending towards Nathan and his awkwardness, actually opens up quite a bit after Nathan confronts him about his days as a pornographic Penthouse model. They even end up tossing around a football.
* "Finding Frances" has a lot of the usual CringeComedy, but adds some genuinely affecting moments (sometimes with a bittersweet aftertaste). The conclusion is very touching but also true to Nathan's comedic sensibility.

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