The 19-year-old singer went to hang out with the 'Hotline Bling' hitmaker at The Weeknd's concert in Toronto, having previously met him on two other occasions, but Shawn was instantly stopped in his tracks by Drake's guards.
Speaking about the altercation on 'The Tonight Show Starring Jimmy Fallon', the 'Stitches' singer recalled: ''We're up on this riser and Drake's also there watching the show along with another few artists. I was like, 'I'm going to go say hi, he must remember me.'
''So I go over to him and touch his side. Next thing I know I'm in the middle of The Weeknd show with my arm hooked behind my back. Drake's security guard has me completely at his mercy.''
The star remembers looking over at Drake, whose real name is Aubrey Graham, and pleading with him to remember his face.
And within the time it took Drake to remember the star and allow his security to let him pass, Shawn feared he was going be locked up.
He explained: ''I see Drake look over, my eyes I knew it was like, 'Help me, please Drake.'
''In that moment, if he didn't know who I was it would've been the most embarrassing, I don't know what I would've done. I would've been in jail.''
Thankfully, Shawn was eventually released by the security guards, although he still found the entire ordeal ''terrifying''.
The singer added: ''For the security guard's sake, he was doing his job, but still it was terrifying. Don't expect everybody to know who you are.''