New dice mechanic?

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thedroid:
I know there are games that use a "blackjack" dice method where you try to roll between two numbers, but are there any that use multiple rolls in this fashion:

Say I want to roll as high as I can, but not over 20. I first roll 3d6. Then I roll 2d6. Then I roll 1d6. I can stop at any time if I'm satisfied with my roll. Like if I roll 17 on the first roll, I can just stop there. But if I roll 9, I'm going to take the second roll. If I roll a 14 on the first roll, I'm faced with a tough call: it might be easy for my opponent to beat me, but I'm likely to go over on my second roll. 

It would work on a Margin of Success, Margin of Failure basis. Going over 20 would mean a MoF of 5 + the amount by which you went over.

For opposed rolls, the player would go first, then the GM would roll and would have to keep rolling until he beat the player's roll or went over or took all three rolls. For unopposed actions, you'd just have a difficulty number to beat, which may or may not be known.

You could rank attributes 1-3. For a 1 you'd get just the first roll. For a 2 you'd get the first and second. For a three you'd get all three rolls if you need them. Skill levels could add to the "ceiling" number. So a skill of 2 would raise your ceiling to 22. At a skill of 5, you'd get an extra die on the first roll, or 4d6. At a skill of 10, you'd get two extra dice on the first roll, for 5d6. An attribute of 2 would have a maximum skill of 5. An attribute of 3 would have a maximum skill of 10. If you have a 1 attribute, you can't gain rank in any related skills.

I'm not sure what sort of setting to apply it to or anything. Right now I'm just looking for a way to put some extra risk-taking and decision-making into the act of rolling dice.

I've also considered a starting ceiling of 18.

My concern is that it's too much rolling. Also, fudging rolls would take away any added fun, so the game would either have to be especially kind or brutal to players' characters.

Certified:
Because it's based on gambling a few things that come to mind are like an old west setting or something like gritty underground. I think you have a solid start for a mechanic starting with 3 dice and working down. I don't think you need to make it that much more complicated. If anything past the basic mechanic I'd say set your target, lets say 20 your original suggestion then offer something like Bust forgiveness based on the level. So if you had a skill of 3 and you rolled 22 you could still count it as a 20. That would mean the highest skill would be a 10 and allow them to roll over with impunity. To limit the power of Bust Forgiveness you might only allow a total forgiveness in a session up to the skill level or only allow it once in a session. For example a character with a skill of 5 rolls over by 3 he forgives the 3. Later in the session he rolls over by 3 again he does not have enough skill to cover the overage and now has to decide if he wants to hold at 23 or reduce his Margin of Failure.

Skill could also be used to determine winners in ties.

Escova12:
Neat stuff. I like the choice of staying or rolling in new dice. One thing you could do here to avoid players feeling like the rolling takes away from the role-playing is have them narrate a part of the action each time they make a roll. For example, if Harry is trying to win a fencing match, on the first roll he would narrate some actions (i.e. sidestepping, landing a point. or, if you want less player-narration; attempting to strike his opponent, trying to dodge out of the way). The GM then fills in with how effective the result is (based on how high their initial roll was). Repeat this process each time you roll in new dice, with the ultimate success or failure being determined by the dice but narrated by the GM.

Really like this guy
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You could rank attributes 1-3. For a 1 you'd get just the first roll. For a 2 you'd get the first and second. For a three you'd get all three rolls if you need them.

On this guy
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Skill levels could add to the "ceiling" number. So a skill of 2 would raise your ceiling to 22. At a skill of 5, you'd get an extra die on the first roll, or 4d6. At a skill of 10, you'd get two extra dice on the first roll, for 5d6. An attribute of 2 would have a maximum skill of 5. An attribute of 3 would have a maximum skill of 10. If you have a 1 attribute, you can't gain rank in any related skills.

An alternative of this could be "fudging" or "moving" the number you roll by the number you have in the relative skill. For example, if Harry has 3 in fencing, and he rolls a 23, he can move the number 3 points, gaining a 20. Alternatively, if Harry rolled a 15, he could boost his number to 18, which is more likely to succeed. Players could have the option of using all the "fudge/move" points at once, or applying some of them after each roll, up to the number they have in the skill. This would also make the set roll goal (20) more consistent throughout the game, rather than dealing with constantly variable roll goals (i.e. 20 here, 18 there, 15 here...).

thedroid:
Good suggestions on keeping it simple and narrating after each roll. I was initially considering having skills allow the player to fudge the roll by the same number of points, but when I tested it myself, it felt like it took too much of the risk away. But I could definitely see having a limited number of chances to fudge instead of a higher ceiling on every roll. The end effect would be to give the player a number of rolls equal to skill that always score the top number.

Maybe I should make the ceiling number 21, to emphasize the blackjack connection. I do think it felt a little riskier at 20, though. 

The rolls are actually surprisingly consistent in their clusters, so I'm worried that, if the two sides in a contest have the same skill, the contest might take too long to win, because the margins of success and failure are so small. Of course it depends on how many points make a victory. But I'm thinking of adding one more gambling option:

After an outcome is determined, you can press your luck and roll a single die: on a 1-3 you cut the margin in half; on a 4-6 you double it. It would be the same whether you succeed or fail. Of course, if you succeed you're hoping to double it, and if you fail, you're hoping to cut it in half. But either could always happen. Hence the risk.

Escova12:
Another thought to consider is whether there would be a rule difference between an extended challenge and an immediate one. Would a chase across the country side use the same mechanics as a sneak attack from behind? Also, would a life-or-death battle be solved in one round of action? This is something I have been struggling with myself as far as game mechanics go. One of the ways I thought of solving it is distinguishing the number of conflicts needed to succeed based upon how difficult (or important) the act is. For example, a cross-country chase (lets say hunting down Dracula) might be a best-of-three sort of challenge. Spotting a decoy he throws up to mislead you in the chase would be resolved with a single challenge. Then, when finally encountering him, the fight is a big deal, so to best-of-three again, or maybe best-of-five. I actually feel like a single challenge answer for each of these scenarios would be cool, but my fear is that major conflicts would be settled almost immediately, and particularly with fights, there may be a drastically high mortality rate.

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