To find out what an orange Mark Rothko painting and miniature masks of the Dan people of Liberia have in common, visitors to the Yale University Art Gallery will have to take a tour with one of the student gallery guides.

Beginning Friday, this year’s student guides at the gallery will debut the tours they have spent an entire year preparing. The program, which started 12 years ago, trains undergraduates to give themed tours around the gallery, incorporating four works of art through a common lens.

The training is rigorous. The group of fledgling guides meet with museum educators at the Frick Collection and the Solomon R. Guggenheim Museum in New York, write around 25 pages of object studies, and learn to cut down on their “likes” and “ums.”

“This program is our cornerstone of undergraduate involvement in the gallery,” said Pamela Franks, deputy director for collections and education at the gallery.

Before Shannon Connors ’12 knew the theme of her tour, she knew a piece she wanted to include in it: She said she was fixated on “The Ankle,” by Basquiat — a work from 1982 which combines the words “LARNYNX,” “SHOE SIZE,” “ASS” with messy scrawlings, medical drawings from “Grey’s Anatomy” and a copyright sign.

In choosing her other pieces, Connors said she took advantage of the breadth of the gallery’s collection. She coupled the work of Basquiat with masks from Liberia and Côte d’Ivoire, the Rothko and a piece of stoneware by contemporary Japanese ceramist Ogawa Machiko.

The theme: tensions between arts that “vacillate between one viewpoint and another.” All objects are split somehow. The masks combine the pragmatic with the spiritual; they are small, travel-ready versions of ceremonial objects. “The Ankle” combines Basquiat’s childhood fascination with anatomy and technical drawings with his later interest in graffiti.

To prepare for the tour, Connors said she uncovered details about Basquiat’s multiethinic background, the timing of Mark Rothko’s name change from Marcus Rothkowitz, and the resonances between the shattered glass in Machiko’s pottery and the artist’s repeated dreams of water.

Some gallery guides chose a theme that is more concrete. Victoria Charette ’11, who will debut her tour this week, focused on a subject that can be summed up in a single word — childhood.

Like Connors, she had no trouble choosing the first object she wanted to talk about. She had written about a piece of African art for a class with history of art professor Robert Thompson and knew she wanted to include it “at all costs.” She coupled it two paintings depicting children, as well as a Basquiat.

Reading through the curatorial files pertaining to “Lady Jean” by George Bellows, Charette discovered the artist’s letters. They revealed that the painting’s subject — a young girl in a dress far too big for her — is the artist’s nine-year-old daughter, whom he painted obsessively. Exhausted by posing for “Lady Jean,” Bellows’ daughter demanded that her father pay her model’s wages. The dress she is wearing is her mother’s, from the 1880s, over 30 years before she was born.

The oversized dress — her mother’s — and her flinty expression create “a look beyond her years,” Charette said. Charette explores the intersection between youth and maturity in the rest of her tour.

Caroline Drucker’s ’11 tour is about how artists create different representations of niches.

“Inside and Outside,” by George Groz, pits together two social classes in two separate spaces — a veteran begging outside a party of war profiteers, while “Still Life of a Forest Floor” by Melchior d’Hondecoeter groups in the same space animals that would normally occupy different niches.

The tours begin on April 16 and a full schedule can be accessed on the gallery Web site.