How to make fighting a constantly-escaping enemy fun?

Question

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.

Answer 1

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.

Answer 2

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 ...

Answer 3

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.

Answer 4

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.

Answer 5

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