Sure, let’s call it that, why not. That’s not going to be completely incomprehensible.
The skill challenge represents one of the many pieces of 4th Edition D&D technology that was underappreciated in its time and misunderstood in hindsight. The Skill Challenge was a tool that let the DM run a non-combat encounter with the same kind of group engagement that the game’s combat system normally demanded; it has a failure state represented by eventual failures, but it also serves to let players platform their own choices and express how they do things. Skill Challenges in the simplest form are ‘the group needs to succeed on X possible checks before they fail N possible checks.’ The system isn’t necessarily all that groundbreaking, but the Dungeon Master’s Guide bothered to explicate a bunch of useful, good ideas about their execution.
There are ideas you might realise are fiction first and fail forward in the 4th edition D&D Dungeon Master’s Guide, but they’re not called that, and people don’t seem to remember what these books were like. What skill challenges let you do was explicitly call for a moment when many people are trying things at the same time, and get to negotiate the fiction of what that means, what kinds of things people are doing, and how their skillsets are expressed. It’s a great system, and I wish more people were familiar with skill challenges, especially in how they do something D&D does well (induce and encourage all players to engage with simple rules tools) and patches something it doesn’t tend to do well (encourage spaces of free creative expression).
Particularly, one thing that skill challenges let you do is bring the moment of the skill into a group scenario, so it’s much less likely to be ‘the skills-focused character goes off on their own for twenty minutes to work out some malarkey and then decides whether or not they tell the rest of the party what they did when they get back.’ Which isn’t a condemnation of those players who liked slinking off like that, but if it was the primary thing that ‘skilled characters’ did it could use up time at the table in an inefficient way; one player takes focus for a distinct period of time and nothing else proceeds while they’re doing it.
Skill challenges address this by adding a dimension of collaboration to all these solitary experiences, just by dint of making sure that there’s a reason to go around the table and ask ‘hey, how are you involved’ in turns, and to encourage players to volunteer stuff. You get to tell how your skills apply, and your skills are all written with a descriptor like ‘use this skill to do this kind of thing,’ so you are invited to imagine ways in which the skills you have could be applied. The skills in 4e are pleasantly broad, too, which meant that a lot of times things like magical locks could be overcome by lockpicking skills under ‘streetwise’ but also could be addressed by thoughtful skills under ‘arcana.’
It’s to this end that this system helped with one of the hardest things to do engagingly in a group environment, which is, bards seducing their ways into fancy locations. Oh, you may be thinking of another more specific type of character, maybe they’re a sorcerer or a rogue or you had an ardent who was inclined to use this as their solution to any problem, but when I said ‘bards seducing their ways into,’ you were already conjuring to mind an example. It’s classic.
It’s also, on the face of it, isolating.
Flirting isn’t really a group activity. Well, okay, it kinda is,
but it’s not meant to be a group activity where you, the subject you’re flirting with (or subjects), and two of your other unrelated and uninvolved friends are all hanging out doing the thing at once. It’s got some intimacy, it’s got some playfulness to it, and that play means that you kind of don’t want to be distracted from it.
On the other hand it is a big point where skills become important, nae, vital to the story progressing, and if you want to use this as a focus, there’s an impulse to make it so it happens briskly and is a yes-no solution, or to say no, don’t worry about it, we’ll find some other solution so I don’t have to sit here and make everyone else engaged with one player flirting with an NPC.
What I’d suggest is to involve the skill challenge here, but also detach it from time. The moment of the skill challenge is in the flirting; up front, head to head, in the conversation with the count or duke or swan-person or whatever it is the flirter has their designs set on. But that moment can be stretched out with a series of references to events that happened in the past that can be treated as important to this moment. Make them into a sequence of flashbacks of other characters in the party building up the flirter, or gathering info on what kind of flirting would work, or even training with the flirter and giving them tools for considering the world from their perspective.
This idea may look a lot like flashbacks from Blades in the Dark and I’d be lying if I said that wasn’t a big influence on how I run skill challenges now. It’s way less interesting to me for players to have to plan ahead of time what they may want to do than let players play characters who are the types who would have done that planning ahead of time, especially since they exist in that universe and the players don’t. This use of skill challenges to stretch out a moment of conversation and then turning that into a collaborative sequence of storytelling across multiple other characters is a great example of the ways you can improve one game by just playing other games as well.
It’s the TTRPG equivalent of ‘read another book’ I guess.