I'm glad to say that when I had this happen in my first session/"session zero", my players didn't care.
Mind it may be because of the circumstances, basically some kids kept trying but failing their Dexterity checks, and finally the kid leading the gang of street urchins got fed up and got the PC to join her in trying to teach the urchins in how to properly pick a pocket by willingly turning around. The PC meanwhile was hopelessly lost and so trying to actually just give the urchins money to serve as her guide in the city.
So what happened was:>Urchin: "Okay, so she's turned around now, she can't see or hear you, and you go like this!">[roll, urchin wins, steals 7 coins from the PC's stash of around 500]>PC: "Okay so you can keep that if you - ">Urchin: "Yeah hang on. [to fellow urchins] Okay, see, it's easy! And now you've got some copper or silver or...GOLD?! RUN! Run run run we're rich!">PC: "Wait, hang on! You can keep it, I just want directions!"
PC proceeds to chase the urchin through the alleys while the urchin shouts back that if she actually gives directions then it's not *stealing*, she was just *paid*, and that's not what she's about.
(None of the "urchins" are actually poor, it turns out, they were just essentially chuuni delinquents).
The urchin finally kind of relented and gave directions in exchange for the PC buying them all coffee, which they weren't allowed to have.
Later in the session I rolled a secret check for another character (the group hadn't come together yet) and the same urchin managed to steal another 4 gold coins, covertly this time. I told the PC that he now had 4 fewer gold and that from somewhere in the crowd he heard a teen girl shout "Foreigners are LOADED!"
The teen's now a sidekick NPC part of the group since they lacked a proper rogue.