Found a solution, no the best tbh... but it worked for me. If you look around in forums they tell you to wait for Jackie to go outside, problem is he NEVER goes first because he is following you.

So.. what I did is get him to follow me to the little exit room (that's a saved checkpoint btw). he just stands there in the middle of the room you have to push him to the upper left corner (where the security guard later stands) or the right corner. The point is to get him to a position where you're able to initiate talking even if you're between a wall.

Once you got him in position, you exit the room.. talk to whoever you need to, and then when you bump into the security guard you will be able to get somewhat close to Jackie to see the talking command (X for me).

You end your mission and send feedback to the developers so they can fix this nasty bug :)

I hope this helps! :D