The "Scream and Shout" singer was casually clad in jeans, a white shirt, black jacket and boots. She wore her hair up in a messy bun and carried an oversized handbag, while her date rocked a Rolling Stones T-shirt, black sports jacket and baseball cap for their night out.
Earlier in the day, the pop star hung out with her mom in Malibu before dining out for the holiday with the unidentified fella.
A rep for Spears has not yet responded to a request for comment on the V-Day outing.
"I'll always adore him and we will remain great friend," Spears said in a statement after the twosome announced their split.
Trawick also echoed a similar sentiment: "I love and cherish her and her boys and we will be close forever."