The 'Keeping Up With the Kardashians' star - who recently split from long-term boyfriend Scott Disick - arrived along to The Nice Guy in Los Angeles, but later left the venue with the 21-year-old singer, who kept his head down as they were pictured exiting the nightspot, before getting into a waiting SUV.
Despite their apparent closeness, it is unclear whether the pair had enjoyed a romantic date as the 'What Do You Mean?' singer is a long-time family friend of the Kardashians and has even babysat for the 36-year-old beauty's eldest son Mason, five, in the past.
Kourtney's mother Kris Jenner previously hailed Justin the ''best babysitter in the world'' after a family pool day.
Captioning a photograph of Justin with Mason, she wrote: ''#Mason & @JustinBieber family pool day!!!#bestbabysitterintheworld (sic).''
And the 'Beauty and a Beat' hitmaker seemed to enjoy the day too, as later he shared the same picture, captioning it: ''cool fan (sic)''
But Kris has reportedly been keen for the pop star to date her 19-year-old daughter Kendall Jenner.
A source previously said: ''Kris would absolutely love for Kendall and Justin to be the next 'it' couple. She adores Justin and thinks he is perfect for her daughter.
''And of course to have him on ['Keeping Up With the Kardashians'], would be a fabulous extra bonus. And believe me, she lets Kendall know it every opportunity she can.''
Kendall and Justin have been linked romantically previously when they were seen dining together in Paris.
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