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Page 274 - Snakes and Ladders
You know, as I write this particular arc surrounding Rarity, it strikes me that the DM and the players really need to be on the same wavelength when it comes to Rogue activities. I’ve been in groups with many a thief, all of them lamenting the lack of opportunities to pickpocket and con people without divine (and party) retribution. But I imagine that’s the result of a group (including the DM) expecting to play a band of heroes whose actions ultimately serve the greater good. A Rogue’s usual motivations tend to get drowned out in that kind of environment.
If a thief’s gonna be thief-y in a roleplaying game, the DM’s gotta be in on it too and be supportive of that. (Other than just saying, “Uh, sure, roll a single skill check.”) And, to a certain extent, so do the players - though it can make for interesting character conflict otherwise, if your group is into that sort of thing. My main point is, though, the DM’s gotta be willing to go the full nine yards to make being a Rogue just as interesting an experience as being a hero.
Actually, I’m worried this is all just conjecture on my part. To you readers with far more roleplaying experience than I: Is any of what I’m saying making sense, or am I just blowing hot air?
 
Transcript:  
Rarity: Hello, everypony! I’m back, but only for a second.
Applejack: We haven’t told the Princess ‘bout you yet.
Rarity: Oh. Well… thank you, I suppose. Regardless… Twilight, might I borrow Spike for a little while?
Twilight Sparkle: Why? Wait, don’t tell me. It’s a secret.
Rarity: Not at all. I have a high-profile client asking for a line of special gem-studded dresses. I’m just a bit short-supplied. I need Spike’s help collecting the gems I need.
Twilight Sparkle: Um… Sure, I guess?
Rarity: Wonderful! I really do owe you one, Twilight. Talk to you later!
Fluttershy: Aww… It’s nice to see we can all stick together despite our differences.
Twilight Sparkle: What just happened? Am I a criminal now?
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