Calypso -- The Rescue
The second Short Trek is an intense retelling of the Greek myth of Calypso, the nymph who fell in love with Odysseus after finding him washed ashore her island. In "Calypso" the U.S.S. Discovery finds a damaged escape pod floating in space and brings it aboard.
Calypso -- Zora
With a thousand years to itself, the Discovery evolves itself into a female-voiced personality with a love of [REALLY] old musical films. The A.I. is so natural in its speech that the rescued Craft mistakes it for a real person. By the way, the cleverness of this script is almost smug -- naming the Odysseus character "Craft" because he is "crafty" which was Odysseus' defining trait.
Calypso -- Taco Tuesday
Like the empty castle from the fairytale,"Beauty and the Beast," which caters to the lost girl's needs, Zora/Discovery not only clothes and feeds Craft, it educates and entertains him with a variety of cuisines and cultural curriculum. Craft's hesitancy feels natural, the reticence of a career soldier as well as the caution of a survivor.
Calypso -- Movie Night
With only a selection of Zora and Craft's interactions shown, the passage of time is still conveyed elegantly with overlayed shots of his daily activities. The production value on this episode is powerfully wielded. Still, we have no idea how long he actually bides with Zora. (In The Odyssey, Calypso keeps Odysseus with her for seven years, enchanted by her singing and dancing.)
Calypso -- S'Wonderful
It speaks to Craft's (ie. humanity's) need to interact that he looks for a way to do "something nice" for Zora, who is essentially a machine despite the complexity of its A.I. Their dance has all the glamorous romance of the era it evokes so when Craft pulls back from the expected kiss with the memory of his actual wife and child, it is quite jarring. The tear that falls from the holo-Zora is touching (if improbable).
Calypso -- True Names
Bottom line: This is a highly speculative, Homer-homage piece that is only tied to the Star Trek: Discovery 'verse by the ship's name. It could've been set in any A.I.-run environment, even a Google smart home a thousand years in our future. That being said, it's well-told with some fantastic visual elements and the intellectual conceit of its Odyssey source material is actualized with great skill.