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(+1)

Arc tends to do that, not tell you if something isn't in the game yet.

But plotwise, the reason you even interact with Jackie in the first place is to get Samantha's key.

You can't do that yet.


The cafe receptionist?
Check the leads, you missed a step...
Probably talking to Gramps.

(+1)

Ah ok, that is good to hear that I wasn't missing anything in regards to the key. And as for the receptionist, I had meant the one at Sally's Company.

(+2)

Oh, then no, you can't date her. 
Just a scene if you talk to her.

People normally ask about "dating the receptionist" referring to the one in the cafe from the main story.