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The music star also wore some silver stud earrings and his hair was styled in his signature heart-shaped design blunt buzzcut.
While Drake stepped out alone on Wednesday, two nights before he was joined by a mystery brunette at the same West Hollywood restaurant.
Stepping out: The God s Plan hitmaker, 34, looked typically suave in a yellow and black leather bomber jacket as he left the swanky eatery flanked by his security team
Style: He teamed the eye-catching jacket with black jeans, trainers and accessorised with a silver watch and gold chains
He arrived at the back entrance of the celebrity hotspot Craig s, while the unknown woman snuck in the front before the pair left at the same time later that night, getting into separate cars.
Drake showcased his casual style as he arrived for a spot of dinner with a mystery woman in West Hollywood on Monday night.
The God s Plan hitmaker, 34, arrived at the back entrance of the celebrity hotspot Craig s, while the unknown woman snuck in the front before the pair left at the same time later that night, getting into separate cars.
Sources claim the pair enjoyed a meal together in a private room, with Drake s security guarding the door.
Casual: Drake, 34, showcased his causal style as he arrived for a spot of dinner in West Hollywood on Monday night with a mystery woman