People-pleasing is an art, and Maria is a professional. "Jack and Diane" takes the familiar feeling of social panic that sets in when you're stuck with people you can't relate to, then drags it to its silliest extreme. The episode is also a terrific showcase of Bamford's voice-acting talent, which she's used to bolster everything from CatDog and Adventure Time to her own stand-up act.
"Jack and Diane" begins with Maria accompanying Bruce to a dinner party at his ex-wife Barbara's house. Nervous about her ability to make small talk with people that seem out of her league, Maria slips into the voice of her fancy-pants alter-ego, Diane. "I'm a natural extrovert, so this is a pleasure," is the kind of thing Diane says in her elegant, sultry tone.
At the party, she meets Jack Tripper (Brandon Routh), a Yale graduate whose unique interests include The Big Bang Theory, coffee, and beaches. Jack falls for Diane immediately because they're exactly the same brand of dull. Maria tries to bail on her impression, but Barbara's upscale guests are convinced, like some people Bamford encounters in real life, that her natural voice is the actual joke. Diane quips that Maria's voice is "almost like a disability." Soon after, as Jack walks Maria to her car, she realizes that she can toggle his romantic interest on and off by switching between her own voice and Diane's.
Larissa and Dagmar don't understand the extent of Maria's dilemma with Jack until they hear her on the phone with him. Diane telling Jack she's carbonating her pool in her solid black tankini and belly chain is just too much to bear, let alone those cringeworthy squirrel kisses she delivers before hanging up.
Of course, this isn't the first time Maria regrets her people-pleasing ways. In the past, we see Susan and a remarkably grating real-estate agent pushing Maria to buy a house. Surely, she can afford a nice house — she's making $10,000 per second lending her voice to Lady Orca, a surefire hit cartoon that's based on SeaWorld and stars Bill Cosby. Never mind Maria's hesitation to purchase a house at this exact moment.
Susan and Maria join the agent, Karen Grisham (played by June Diane Raphael and not to be confused with Ana Gasteyer's Karen Grisham), in her office, where she takes them on a Sims-esque virtual-reality tour of different houses.
Maria ultimately buys the adorable house she has in the present day, complete with a recording booth for voice-over work. To her disappointment, Susan isn't happy, even though she basically bought the place to please her. Instead, Maria's friend thinks she's rubbing her face in this newfound Hollywood success. If you can consider Lady Orca a Hollywood success, anyway.
We're back in the present day, watching Maria perform stand-up in Diane's voice. Jack loves it. He is unsettled, however, by Patton Oswalt casually calling Maria "cunt" and "whore" as terms of endearment. Jack spends the rest of the episode trying to figure out how to use insults as charmingly as Patton does. Watching him repeatedly fail at inappropriate times is a highlight.
At least Maria's love life is going better than Bruce's stunted one. Barbara's new partner moved in and wears all of Bruce's clothes, while he is stuck living in a dorm room where he endures brutal hazing. Maria offers to let him move in, too, but Bruce won't have it.
Instead, he pressures Maria into helping him in a different way: He urges her to take a job hosting what truly sounds like the worst game show of all time, Lock Up a Broad. (Not to be confused with Locked Up Abroad.) Maria thinks it sounds misogynistic, but Bruce thinks locking women in a box and forcing them to apologize to their partners for minor transgressions is ironic humor.
Maria, God bless her, takes the job. When we see her taping an episode, it seems like she's channeling Bill Hader's hilariously creepy Keith Morrison impression, or maybe just Morrison himself.
As awful as the gig is, it might not be a worse experience than the data-entry job Maria worked in Duluth. Her co-workers are entranced by jokes from the office clown, Danny (Nathan Cousins), whose sense of humor is on par with Michael Scott's, right down to the "That's what she said" jokes. Maria, donning impossibly drab outfits that scream "awful desk job," seems to be the only person who ever does any actual data entry.
That's probably because her co-workers have no interest in Maria's awkward brand of humor. Maria's only work friend is her mother, who shows up unannounced with a box of tampons she forgot one morning. Before leaving Maria to plug away at her data entry in peace, her mother encourages her to seek approval from herself and not worry so much about what other people think. It's simple but valuable advice, although we already know she'll have lots of trouble heeding it going forward. To her credit, Maria correctly points out that stand-up is all about getting approval from strangers, in a sense.
Present-day Maria is tired of seeking Jack's approval, and Jack feels the same way about seeking hers. He reveals he has no sense of humor at all — not a terribly shocking announcement by this point — and has been faking it to please her.
As they toast to just being themselves, Jack lets out a 30-second fart. Maria, a noted fan of fart jokes, laughs, and he gets mad at her for not taking his flatulence seriously. That's the last straw for Maria, who breaks up with him right then.
As a parting gift, she leaves Jack a voicemail from Diane, rattling off a series of fancy terms that includes strawberry rhubarb, potato gnocchi, and candelabra. Before the credits roll, we're blessed with a music video for "People Pleaser," starring Maria.
The lyrics leave us with the moral of the story: "Before you pleasure someone else, you must pleasure yourself." If she ever manages to internalize that lesson, Maria's life may get a lot less entertaining. The delight of this episode, and of Lady Dynamite as a whole, is that Maria's blunders in past and present give us permission to learn from our own mistakes. Answers aren't found in the flip of a switch; nobody can instantaneously change their behavior. Moving on from failure is often a painfully long process. And as Lady Dynamite makes clear, it's okay to laugh about it.