The couple stepped out in New York City Wednesday night, just ahead of Valentine's Day on Thursday. They were spotted leaving Zuma, a Japanese restaurant in midtown Manhattan.
Simmons, wearing all black and silver and gold necklaces, walked ahead of Jenner as they exited the restaurant. Meanwhile, Jenner stayed behind her boyfriend as she walked out, sporting light jeans, furry heels, a graphic T-shirt and a leather coat.
The pair appeared serious as they made their way to the car, with Jenner looking down at the ground as she walked.
Later, the couple held hands as they headed to Marquee New York, where they danced the night away to a DJ set by Chantel Jeffries. Their date night followed 22-year-old Simmons' game at Madison Square Garden, where his team, the Philadelphia 76ers, beat the New York Knicks 126 to 111.
The couple's pre-Valentine's date night came about a week Jenner's confirmation on The Ellen DeGeneres Show that she and Simmons have been dating "for a bit now."
Prior to her reveal, the pair had often played coy about their relationship by leaving flirty comments on each other's Instagram accounts. Additionally, Jenner is often seen sitting courtside at Simmons' games.