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The trick here is I'm talking about something low-level, something the PCs should by all accounts be able to squash in a heartbeat...but it keeps escaping. Every time. And no matter how elaborate they get with traps and attacks, it keeps worming free and showing up again later.

I'm worried a set of encounters like the above takes away too much player agency, but as a storytelling element it would all be in good fun. Does anyone have experience with this sort of "gimmick fight"? Was it fun or frustrating for you every time their smug little face popped onto the playing field?

Context

The first ever fight my group (two people with limited D&D experience) had went terribly, terribly wrong. It was also my first time GMing, and I had thrown them against two bugbears and misjudged how much damage they were going to do. It ended up feeling like a seventeen hour fight with pool noodles for how little actual bloodshed there was, and eventually one of the two bugbears threw his buddy in the line of fire and used his body to escape. Hilarious at the time, and a good story we bring up constantly as a joke any time anyone starts rolling poorly.

Extrapolating from that, I think it'd be equally hilarious to have a (very) occasional fight against bugbears that the PCs are pretty much guaranteed to lose. No deaths, just a set of cowardly foes who refuse to hang around long enough to get their rear ends handed to them and choose instead to book it as soon as the going gets tough.

Obviously from my perspective this seems like a super funny in-joke, but I don't want to annoy my players, so I'm looking for anyone with experience of a similar scenario.

In answer to the comments; We're a rp-heavy group, both players are 4th level dual-classing (4/1 splits), and as a group we've only been playing together about 8 weeks. The tone of the game is generally fairly midline between humor and seriousness - we break character a lot to laugh and there's been plenty of in-character jokes too, but when the moment calls for it we can buckle down and get gritty. Most encounters right now are either easy wipe-the-table roadblocks, or semi-challenging encounters that require strategy but don't typically knock the PCs unconscious. The bugbears - if in the right number and with a terrain advantage - could probably do significant damage to the party, but there's functionally zero risk of a TPK.

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  • \$\begingroup\$ This might be better suited to a forum, rather than an SE site....as there is no single, definable 'right answer' to this. \$\endgroup\$ – guildsbounty Apr 26 '17 at 17:51
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    \$\begingroup\$ @guildsbounty If it attracts low quality answers or downvotes I'm happy to delete \$\endgroup\$ – Alex Apr 26 '17 at 17:52
  • \$\begingroup\$ I still think this is a bit too opinion-based...but Pyrotechnical is right, this depends very heavily on your players. I've known some that might be cool with this sort of 'I'll get you next time, Gadget!' shenanigans...and others who would get mad at me for it. \$\endgroup\$ – guildsbounty Apr 26 '17 at 18:00
  • \$\begingroup\$ You say "PCs are pretty much guaranteed to lose" in paragraph 4. Is that what you mean? That doesn't seem like a fight with an escaping enemy to me, if the enemy knows it will win the fight. \$\endgroup\$ – Icyfire Apr 27 '17 at 0:20
  • \$\begingroup\$ @Icyfire I wouldn't say the bugbears "win" so much as they get to leave with their heads intact. By the same logic the PCs can't win, since their enemy escapes, so I went with "lose". I guess an argument could be made that "the PCs are pretty much guaranteed to not win" would be the better phrasing. \$\endgroup\$ – Alex Apr 27 '17 at 2:12
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This is the sort of thing that can be fun, but it's also possible that things will become frustrating. In particular, having meaningful objectives that are thwarted again and again through no fault of your own can get very frustrating.

My suggestion would be that if you're going to do this, don't have it stand in the way of the PCs doing whatever it is they came to do. If your objective is to kill the bugbears, and you simply can't kill the bugbears no matter how hard you try, that gets frustrating. If your objective is to get into the fort (that the bugbears are guarding) or assassinate some other guy (that gets thrown at you by his bugbear bodyguards to cover their own retreat) or to track down information (including clues that the bugbears leave behind) then that's much less likely to be frustrating. There's also a lot of easy ways to play that sort of thing for laughs.

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If this is an occasionally recurring running joke, not relevant to the party's primary missions, you can probably get away with this and have it be fun rather than frustrating. If it is (or becomes) relevant to the party's progress or goals, though, there will need to be some sense of accomplishment, each time it happens -- a closer escape, treasure taken or minions defeated each time, that gives a fair hope that next time ...

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This can be fun but be careful not to misread the players

If your NPC is guaranteed to escape due to GM fiat, then no, it won't be fun, it'll be irritating. If you design him to have a high likelihood of escape and he escapes a lot, then more power to you, but in order to preserve player agency and fun, accept it if the rolls don't go the NPCs way and the characters get them. If the players are hanging on the roll of the dice, it's fun. If they're just hanging on you deciding whether to let them succeed or not, then you're just obstructing them and that's no fun at all.
You might consider making him squirrely enough to weasel his way out, but if they simply end him, then that's that. Forcing the escape will simply be frustrating.

This kind of thing requires reading the table well. Players love to have enemies they love to hate, and a cowardly foe who pops up, causes problems, then 'woop woop woops' away when things go south is a blast, especially if they finally do get him after several failed attempts. The thing is, if they try to curb-stomp him with a vengeance, or start getting edgelordly and grimdark in their planning, that's a clue it's going too far, and even getting the NPC in the end will feel more like 'good riddance' than a good time.

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  • \$\begingroup\$ At one of my tables, we've had revenants come back and back...and back. ITt started off as interesting, but then became unfun (especially as the DM also stopped giving XP for those encounters.) \$\endgroup\$ – NautArch Feb 27 at 16:04
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Answering you strictly, from my experience playing video games and with tabletop groups:
Yes, it can be fun.

Such a character will provide you with plot hooks, and is even a common trope in fiction.
It would add to the level of character immersion, if done right, as well, appealing to the RP-heavy side of your party's play style.

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    \$\begingroup\$ The question reminded me of Ultros in Final Fantasy VI. While I wouldn't have missed it if they had removed it from the game, it was sort of funny. \$\endgroup\$ – Raj Feb 27 at 16:43
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There was a story on the r/dnd subreddit about this called Shane the Shy. It was made with 3.5e, but the idea and enjoyment are system agnostic

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We're looking for long answers that provide some explanation and context. Don't just give a one-line answer; explain why your answer is right, ideally with citations. Answers that don't include explanations may be removed.

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    \$\begingroup\$ This could be improved if you quote what relevant texts are found in the link (because links die), and how it answers the question. \$\endgroup\$ – daze413 Apr 27 '17 at 2:37

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