Like many rogues, my character likes to cheat at cards and steal from NPCs if he thinks they deserve it.

However, the vast majority of D&D towns are small enough that everyone knows everyone. I'm yet to visit a town in my current game where someone hasn't mentioned that they don't recognise me therefore I must be a newcomer.

How can I act like a rogue without the townsfolk immediately putting two and two together that I'm the one responsible for thefts, even if I disguise and sneak perfectly? After all, nobody's stolen anything for years until I showed up (because it's a small town and everyone knows everyone). I'd quite like to be able to use my huge stealth/deception modifiers to avoid becoming an outlaw of each town by default.

  • \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. Good Luck and Happy Gaming! \$\endgroup\$ – Someone_Evil Apr 10 '19 at 9:47
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    \$\begingroup\$ Welcome to RPG.SE! Take the tour if you haven't already, and check out the help center for more guidance. As written, this seems quite broad to me, and heavily dependent on how the DM runs the NPCs - but it can probably be edited into an answerable form. (Also the title is somewhat misleading; nothing about playing the rogue class inherently implies "liking to cheat at cards and stealing from NPCs "...) \$\endgroup\$ – V2Blast Apr 10 '19 at 9:48
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    \$\begingroup\$ Also I question your assertion that because everyone knows each other nothing ever gets stolen. As a person who lived most of my life in a small (>1000 pop) village, there is drama all the time. Granted, newcomers are often viewed as suspicious, but that's a separate problem imo. \$\endgroup\$ – Pierre Cathé Apr 10 '19 at 10:03
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    \$\begingroup\$ @PierreCathé: I'd suggest using that as a basis for an answer. \$\endgroup\$ – V2Blast Apr 10 '19 at 10:04
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    \$\begingroup\$ @V2Blast Honestly I don't think it's that relevant to the question since OP is asking from a player's perspective. If they were the GM and asking how to handle a thief in a small village then it would be more on-topic. \$\endgroup\$ – Pierre Cathé Apr 10 '19 at 10:11

Whilst it is the most common interpretation, being a rogue doesn't mean you have to rob/cheat people.

The classic rogue is good at talking to people, sleight of hand and acrobatics. These skills could just as easily be applied as a mundane magician (like we have IRL), a gymnastics performer or even a security consultant (google for thieves who went legit, using their skills to show people the weaknesses in their security).

However, if you are dead set on using your skills for the classic selfish cheating rogue, your best bet is to go somewhere where everyone does not know everyone else. Towns and cities for example. Those small settlements where it's all one big family have that safety net of knowing who you can trust. It's not worth the effort to ingratiate yourself into that just to rob them when people in the big city have more money anyway.

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  • \$\begingroup\$ The first two paragraphs don't answer the question at all, but simply respond to a misleading title which has now been edited to be more accurate. The last paragraph is the only one that approaches an answer, if your main point is "you can't do it; pick better targets". \$\endgroup\$ – V2Blast Apr 10 '19 at 10:03
  • \$\begingroup\$ The last paragraph answers the question as written, though in my case it's a disappointing answer because my character is already in the biggest town he believes to exist. (I left that out of the question to make it more generally applicable, not sure whether that's best practice here.) \$\endgroup\$ – benplumley Apr 10 '19 at 10:06
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    \$\begingroup\$ @benplumley This site actually works better when you ask about your specific situation so including any details of your particular case is often encouraged. \$\endgroup\$ – Sdjz Apr 10 '19 at 10:35

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