“Insouciance” keeps Jimmy and Gretchen’s ‘relationship,’ as Jimmy puts it in heavy quotation marks, very casual.  They talk and joke like they’ve been friends for life, but keep things straightforward.  Both still acknowledge how horrible they are.  After learning that Gretchen lied to the Spice Girls, Jimmy says “Dishonesty to spare someone’s feelings belittles everyone involved.  Dishonesty to get free stuff is just smart economics.”

This episode also introduces two running jokes of the season: Jimmy’s chronic masturbation is one of them.  He loves to entertain himself- don’t we all?- and whenever we’re in his room, there’s almost always the same bottle of lotion on the table next to his bed.

The other joke is that Gretchen and Lindsay love to try free samples at the local frozen yogurt shop, but they never actually buy anything, much to the annoyance of the clerk behind the counter.  Think of the shop as the water cooler at work where employees talk about their day.

At this point, there’s still no sign of emotional attachment between the two.  As far as Gretchen is concerned, this thing they have is just for fun.  Jimmy doesn’t see a need to ask Gretchen what she’s looking for in this ‘relationship’ because they’ve acknowledged that it can end any time.  To them, this is just a game, with one trying to top the other.

We see this play out in the episode’s opening when Jimmy tries to masturbate with Gretchen in the room, but he can’t do it with her glaring daggers at him.

Edgar still plays the voice of reason.  He knows that Jimmy and Gretchen should and probably will end up together, but he goes a step further when he tries to set up a date between the two.

He is, in effect, the sidekick, which goes hand in hand with a conversation he and Jimmy have about identifying the villain, hero, sidekick, foil, and fool of Ferris Bueller’s Day Off, with Jimmy convinced that Cameron is the villain.  This feels like a conversation you’d get on an episode of Seinfeld.

Problem is that Edgar can’t think up a good reason why Jimmy wouldn’t just ask Gretchen himself, but it’s been established that these two are trying to keep emotions out of this thing they have.  Gretchen’s reaction to the date is one of confusion, as if she can’t believe that Jimmy would even want to ask her out.

But the date isn’t romantic or magical.  Rather than ask each other questions, they mock the idea of having to make a reservation and question why people would take photos of their dinner, a concept that I myself still don’t understand.  There are long, awkward pauses where the two don’t say anything because they aren’t conventional people.

Gretchen doesn’t want the exotic drink that Jimmy gets her, she wants something regular.  Gretchen even shudders when Jimmy awkwardly tries to put his arm around her.  Some would find that move charming, but to them, it’s unnecessary.

Also unnecessary for them is the idea of communal sitting.  This is supposed to be an intimate setting where, if you want to, you bond with the others at your table, but not these two.  There’s even some ripping on new-age dishes with Jimmy outraged at the price of pasta he thought was made of bald eagle’s foreskin, which he only assumed because he couldn’t think of anything soft and expensive.

One key difference between the two here is that Jimmy is quicker to retort with a sarcastic barb or remark, such as asking the waiter if the menu is electronic, in response to the waiter explaining how the menu works.

Here’s what makes the dinner scene work: Jimmy and Gretchen clearly don’t want to be here, but they’re sticking it out because to back out would make them quitters.  But while they try to do that, we also see them bicker like an actual couple when Gretchen brings up her period and how Jimmy figured he would see her in five days, when he assumed her period ended.

She held onto that because the comment, small as it may be, stuck with her.  Why hold onto that when, as you point out, there’s no attachment and it’s just for fun.  The two should just say whatever they like, right?  No.

At the end, Jimmy and Gretchen are still indecisive about whatever they are, as Gretchen isn’t ready to explain to everyone what it is she has with Jimmy.  Jimmy feels that he had to take Gretchen out after how she reacted due to the period remark, but Gretchen didn’t want Jimmy to automatically dismiss her as a person the second she wasn’t available for sex.

The two think this ‘thing’ much further than they should for two people who are convinced that it won’t work out.  We learn that Gretchen actually does like the communal setting, but not with Jimmy.  Not yet.

So how do the two end this night?  They get take-out and bring it into a movie theater in one of the rudest, yet funniest endings of the show.  And then they have the audacity to take an attitude with people telling them to be quiet since, you know, others want to try and watch the film.

They crack open beers and rifle through their bags like they’re the only ones in the theater.  Jimmy and Gretchen are not two people you’d ever want to associate with, yet at the same time, I love them for the pathos and chaos they bring with them because they feel they’ve done nothing wrong.

And to cap it off, they steal the local bookstore owner’s cat.  This will become more important later.  Not now, but later.

So “Insouciance” shows Jimmy and Gretchen just being friends, but also being careful not to cross that line from just being friends to something much more.  When I first watched this show, I wondered if it would fall into a ‘Will they, won’t they’ pattern every week, but the writers found a way to keep it fresh because Jimmy and Gretchen’s plans usually end up hitting a snag or not working out altogether.