Family Riddles

Family Matters is the first episode of season one of Greater Boston, and the first episode overall.

Interviews
Jeff Van Dreason asks Greater Boston residents what they love about Boston. Later, he asks if they know any good riddles.

Part-Time Cryptozoologists
The segment opens with a selection of riddles from BB Bosco's Big Book of Riddles. The answers are not provided.

Dimitri Stamatis, who has been hunting for The Sasquatch, writes to his eldest brother Leon Stamatis to tell him that he no longer believes Sasquatch is real. On his hunt, he met Timothy and Tiffany Ludlow, a pair of Sasquatch hunters who take him under their wing and guide him in his hunt. They take Dimitri to their camp and tell him stories about all of their close calls hunting Sasquatch. He lived with various hunters for six months, searching for Sasquatch but slowly losing faith.

One night, while looking for Sasquatch, Dimitri observed the Ludlows in the forest. Both of them caught sight of each other and assumed that they had seen Sasquatch, not realizing who it really was. This marked Dimitri's disillusionment with hunting for Sasquatch, and he decided that Sasquatch was not real. He explains that he likes mysteries, where Leon likes solutions.

Dimitri announces that he hitchhiked to Portland and met a man in a submarine. He plans on going with the submarine crew to explore the ocean, and tells Leon he will write when he can.

The Famous Bobbin Winder
An ad plays for Singer Sew-and-Vac in Somerville.

The MC at the Someday Cafe introduces Nica Stamatis, who will be performing a monologue at their open mic night. Nica mentions that her brother Leon is there to watch her, and announces that she has decided that she wants to be famous.

As a child, Nica almost met Chevy Chase at a video rental store, which led her to want to be famous. In high school, she began working at an upscale sewing shop, and began repairing sewing machines. She describes other brushes with fame, including meeting one of Leon's professors with a famous son, and working with someone who was later in The Princess Diaries.

Nica says that now she works at a less upscale sewing and vacuum repair store, and that she recently repaired Amanda Palmer's sewing machine. She concludes that she must be getting close to being famous.

Disaster Planning
The Narrator describes Leon's death. Leon and Nica went to the Wonderland amusement park so that Nica could cheer up Leon after a recent breakup. Together, they boarded the Whirlodon roller coaster, where Leon reflected on the end of his relationship with his most recent girlfriend, Louisa. She had been too spontaneous for Leon, who preferred order and predictability. He thinks about how he needs safety nets, assurance, and the elimination of the unknown. He also thinks about applying for jobs, despite being settled into his own job, and how he recently applied for a position at an astrology magazine.

As the Whirlodon reaches the top of its hill, Leon looks out and realizes all of the endless unpredictable possibilities. He comes to realize that he cannot eliminate the unknown, says aloud "Nope," and dies on the spot.

Cast
In order of appearance:
 * Dimitri Stamatis - James Johnston
 * Nica Stamatis - Kelly McCabe
 * Leon Stamatis - Braden Lamb
 * Narrator, Singer Sew-N-Vac pitch man - Alexander Danner
 * BB Bosco, Someday Cafe MC - Jeff Van Dreason

Trivia

 * Tiffany Ludlow later reappears in Dear Leon 1, voiced by Blair Dawson.
 * Leon briefly mentions the North End and the Molasses Flood. In fiction, the North End is still sticky and coated in molasses after the flood, over a hundred years ago.

Content warnings

 * Strong language
 * Death (non-violent, ambiguous suicide)