Synopsis: Linda is bored with Date Night with Bob and decides a seaplane flying lesson is just the thing to spice up the relationship – only she winds up alone with Upskirt Kurt [Will Forte].
Details: Linda and Bob have Date Night but Linda is getting bored with it because Bob always wants to go to the same restaurant and get the same thing. So, to spice up the relationship, she decides seaplane flying lessons are the spiciest idea she can have. Unfortunately, Bob does not share her mundane date night opinion nor her spicy seaplane idea and refuses to accompany her. After a stubborn snit, this leaves her to determine that she will go anyway – by herself – which puts her in the clutches of Upskirt Kurt, the wily, womanizing seaplane flying instructor.
After Linda has departed for seaplane flying instructions, building owner Mr. Fischoeder [Kevin Kline] comes by to warn Bob about not only Upskirt Kurt himself but all his crafty tactics to bed bored housewives – including taking them to the notorious kissy island, Quippiquissett.
Once faking a crash landing on the island secures Linda’s emotions are going in the right direction for seduction, Upskirt Kurt pulls out the Prosecco, cheese, crackers, blanket and lute to begin the seduction process. Linda is only interested in the wine, cheese and crackers – not so much the lute – and is oblivious to Upskirt Kurt’s ploy until he begins unbuttoning his own shirt and making the forward moves. Once Linda sees what’s coming at her, she headbutts him into submission.
After Mr. Fischoeder and Tina have worked Bob up into a lather over the distinct possibility that Upskirt Kurt is indeed attempting to seduce Linda, he takes the kids down to the dock where they hop a ferry to get to a nearby island – only to see Mr. Fischoeder ride by them in his big, expensive powerboat – and finally hop a ride with the island mailman and steal a dinghy which they row to get to the kissy island and rescue Linda.
Once on the island, Bob confronts Upskirt Kurt but he’s too tired from rowing the dinghy to do much other than punch Kurt’s butt and while this ruckus is going on, Mr. Fischoeder has used his big powerboat to tow away Upskirt Kurt’s seaplane.
This becomes their method of escape from the island with Mr. Fischoeder towing the seaplane behind his powerful boat – but while trying to impress Upskirt Kurt of his boat’s power, he goes too fast and launches the seaplane in the air, parasail-style, behind them, forcing Bob to cut the tow rope when they approach a bridge and Linda to take the controls of the plane to land it safely.
The Poop and Skinny: Gene likes breadsticks, so we can only assume Bob and Linda have been spending Date Night at the Olive Garden.
Upskirt Kurt names his seaplane, Shoshana, a similar name of the notorious teenage girlfriend of then-38-year-old Jerry Seinfeld.
The ToonZone Gold Best Line of the Episode Medal – “There’s probably someone out there for you – some freak,” – Linda, trying to console a fake crying Upskirt Kurt
The ToonZone Silver Second-Best Line of the Episode Medal – “I feel like Amelia Earhart! Okay, she died.” – Linda when she is trying to emergency land the seaplane.
The ToonZone Bronze Third-Best Line of the Episode Medal – “I would have punched you but I’m holding wine!” – Linda, explaining to Upskirt Kurt why she headbutted him.
Right Side Store Neighbor of the Week – “Don’t Go There – Cautionary Sign Store”.
Van of the Week – “Cockroach Blockers”.
Burger of the Week – Sprouts! Sprouts! Sprouts it all out Burger.