The superstar, 33, cut a low-key figure alongside his stylish DJ girlfriend, 30, as they enjoyed a romantic date night at celebrity hotspot Giorgio Baldi.
The Weeknd – name Abel Tesfaye – was layered up in a black tracksuit and padded coat, teamed with a white T-shirt and trainers.
He completed his ensemble with a Harley Davidson baseball cap, while his other half opted for a more chic look.
Simi put on a leggy display in a thigh-skimming mini dress, which she wore with a flat pair of baby doll shoes and an oversized greige blazer.
After first sparking romance rumors last year, The Weeknd was spotted locking lips with Simi at his birthday party in February.
The superstar singer and the DJ – who’s his ex Bella Hadid’s former friend -shared a passionate kiss at the songwriter’s 32nd birthday in Las Vegas.
Rumors first swirled about the two being an item last April, and the duo sent tongues wagging because of Simi’s previous friendship with Bella.
Simi is a part of a DJ act with her twin sister Haze Khadra, known as Simi and Haze, and the pair launched their own beauty line SIMIHAZE BEAUTY last year.
Their big brother Fai Khadra frequently appeared on E! reality series Keeping Up with the Kardashians due to his friendships with Kourtney Kardashian and Kendall Jenner.
Before Simi, The Weeknd enjoyed high-profile romances with Bella Hadid from 2015-2019, as well as two-time Grammy nominee Selena Gomez in 2017.
And the Saudi-born socialite previously dated Grown-ish actor Luka Sabbat in 2021.
A fan theory emerged that the Canadian-born musician, whose real name is Abel Tesfaye, ditched his gigs Down Under because they clashed with the Billboard Music Awards.
The singer, who has been nominated for 13 of the prestigious industry awards, is now expected to appear at the ceremony, which takes place on November 19 in Las Vegas.
Many are speculating online that The Weeknd will now take the stage with Ariana Grande to perform to Die For You (Remix) during the BM Awards.
The song has been nominated for 5 awards, including top R&B song.