The 25-year-old “Baby” singer stood out in a neon green hoodie with an orange Drew baseball cap. He added beige pants and brown sneakers with decorative straps.
Hailey, 22, looked fashionable in a gray turtleneck, long black coat and matching over-the-knee boots. She accessorized with gold hoop earrings and large black sunglasses.
The two had a somber talk before climbing in their car.
Hailey was later seen leaving a lunch date with a friend at the Italian restaurant Il Punto in midtown Manhattan.