The group enjoyed dinner at Giorgio Baldi, a Italian eatery and celeb hotspot in Santa Monica, California.
Hailey and Justin rocked chic ensembles, and matched in black as they were photographed stepping out of the restaurant, while the "Peaches" singer escorted his ladylove to their waiting car.
Hailey stunned in a more formal little black dress that she paired with black boots and a diamond-encrusted necklace. Justin, meanwhile, rocked a black jacket and grey slacks, along with a white T-shirt and a colorful knit sweater-vest.
Meanwhile, Kendall and Devin looked adorable as they left the restaurant, hand-in-hand, and walked past photographers.
Kendall showed off her newly colored locks and rocked a semi-sheer black and brown top which she paired with black leather pants. Booker, meanwhile, rocked a pale pink shirt and a tan jacket with white jeans.
"I started having stroke like symptoms and was taken to the hospital," Hailey wrote in an Instagram post. "They found I had suffered a very small blood clot to my brain, which caused a small lack of oxygen, but my body had passed it on its own and I recovered completely within a few hours."
Hailey described the experience as "definitely one of the scariest moments I've ever been through," thanking her doctors and nurses for their help.
Justin spoke about it last Wednesday, during his Justice World Tour stop in Denver, Colorado. The topic came up after his show was interrupted when the power went out right in the middle of his set.
"You know, it's kind of crazy how life randomly throws you curveballs," the 28-year-old singer said once it returned, in a video shared to his Instagram account. "You know, we can't really control much. You know, tonight the power cutting out. Obviously, you guys know, most of you probably know or seen the news about my wife."
"But she's OK, she's good, she's strong," Justin shared, explaining that his wife is on the mend. "But it's been scary, you know? Like, it's been really scary. But I know for a fact that God has her in the palm of his hands and that's a good thing."