At Grill Bon in Tokyo’s Ginza district, Jay Liu, a watch collector, and I sat side by side at the counter, watching the staff as they assembled the restaurant’s signature deep-fried beef tenderloin cutlet sandwiches: lightly toasted white bread layered with sauce and meat, served with pickles and a side of salad. Mr. Liu gestured toward illustrations of Kabuki makeup styles on the wall. “Kabuki actors sometimes come here to eat,” he said, as his cuff shifted just enough to reveal a white gold Rolex Day-Date from the 1970s on his wrist.

He enjoys Kabuki, the traditional Japanese theater with its stylized movement and painted faces, even if he doesn’t fully understand what’s being said. “You can still appreciate the nuances,” he said — a word he returned to when talking about watches. Mr. Liu, 30, who lives in Hong Kong and travels regularly to Tokyo, was guiding me through some of his favorite spots in the city during a recent visit, sharing the watches that matter most to him along the way.

His interest in watches dates back to a visit he made about 12 years ago to an auction in New York, where he had gone to look at Chinese ceramics, but ended up in a space filled with vintage timepieces. Arranged alongside bowls and porcelain from the 1920s, ’30s and ’40s, the watches struck him differently. “I used to think of them as modern, luxury consumables, just things you could buy,” he said. “But seeing them presented next to antiques, you feel that they are also part of history. I immediately felt the connection.”

The Rolex Day-Date on his wrist is a case in point. “It’s a really meaningful one,” he said of the timepiece. A friend gave it to him after a trip they took together to Dubai. “At the end of the trip, he took off his watch and gifted it to me,” Mr. Liu said. “I was moved by this gift.”

Several years later, its meaning has only deepened. “If I could only keep one watch, this is the one I’d keep,” he said.