D&D 5E Flying Tiefling question

So I’m playing a tiefling warlock that has made a pact with a Prince of Earth. I get Featherfall from it, so I was wondering if I could fly up in the air dive down at full speed with my staff and cast featherfall at the last second after I hit the enemy. How much extra damage would it do? Feather Fall is a reaction so I see no reason why this wouldn’t work.
So you are using yourself as a cannon ball. You take the same damage as you deal.
 

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Normally I appreciate creative requests, but I don't see how this would work. There are simply too many things going on, all at once.
  • You hit, have to hold on to your weapon wait for it to fully impact and then still cast a spell?
  • There are no special rules for extra damage on a charge in 5E.
  • If you're using Dex for your attack stat then your damage is about accuracy, not force. Doing this would actually make it more difficult to hit.
  • How are you holding on to the weapon? If you're using strength for the attack, by default you're already putting pretty much all the oomph you can in to your hit anyway.
There are just some things that the rules can't really handle well and this is one of them. I would rule that it wouldn't work but the only opinion that matters is that of your DM.
 

So I’m playing a tiefling warlock that has made a pact with a Prince of Earth. I get Featherfall from it, so I was wondering if I could fly up in the air dive down at full speed with my staff and cast featherfall at the last second after I hit the enemy. How much extra damage would it do? Feather Fall is a reaction so I see no reason why this wouldn’t work.
By the book? Zero.

How I would rule it as DM: Also zero. I normally allow a character who makes a "falling onto the enemy" attack to split the falling damage between themselves and the target. If there is no falling damage, there's nothing to split. You negated the extra momentum that would boost your damage.
 

D&D is an RPG. A Role playing game. Characters play a role in a story. The game is at its best when we tell a good story. This sounds like something very cinematic and dynamic - a good story.

D&D is also a game, and games have rules and balance considerations. So, if a creative player comes up with a creative way to be more effective, the story needs to have a creative offset.

The way I would rule it: You're aiming for split second timing, whether you are casting a spell or pulling out of a dive. If you're off, you either kill your momentum and throw off your strike by pulling out early, or you hit ground by pulling out late.

You can attempt a Dexterity (Arcana) check for Feather Fall timing or Dexterity (Acrobatics) for pulling up when flying (as dexterity is the ability for split second timing). The DC would be set by the distance you fall: (12+1 for every 10 feet you fall).

If you fail, you are too late and take damage for falling. Roll a d20 and add your proficiency modifier. If that exceeds the AC of the target, it also takes the falling damage as you land on it.

If you succeed, but do so by only up to (1 per 10 feet fallen), you pull out early and either lose the attack (if flying/using acrobatics) or feather fall down to the enemy and get to make a normal attack when you fall to them. You stop early by 10 feet per point over the DC you get. Count the feather fall distance against your movement available that turn.

If you succeed by (1 per 10 feet fallen) or more, you get to add 1d1 per 10 feet of damage fallen to your damage to your attack role and crit on a 19 (if you hit) or 20.

You must make a strength saving throw, SC 15, to maintain your grip on your weapon if you hit the ground or hit the target.

So, as an example: You are 30 feet up and attempt to dive and use feather fall to halt your momentum right before after you hit the target, but before you hit the ground.

Your DC is 12+3 = 15 for Dexterity (arcana).

If you roll a 14 or less, you make a d20+proficiency roll to see if you land on the target. If so, you both take 3d6 falling damage. If you miss, only you take it.

If you roll 16, 17, or 18 you will cast the feather fall 10, 20 or 30 feet early, respectively. You'd feather fall down and could make a normal attack.

If you get a 15 or if you get a (19 check or above) on the check, you'd get to add 3 to the damage.

If you roll a natural 19 or 20, you get to deal a critical hit. As the +3 damage were d1s, they are doubled on the critical.
 

Wouldn’t it be just as effective, if not more, to simply drop the spear on them?
It wouldn’t impart some of your mass as force, then. While it would still have much great velocity than a normal thrown spear, I wouldn’t give any bonus damage, just extended range.

Well that would require a STR check though, to see if you can hold on to your spear.
Oof, as a DM, no thanks. I want a single action to have as few rolls as possible.
 

Oof, as a DM, no thanks. I want a single action to have as few rolls as possible.

I agree, but that's also probably why I wouldn't allow it. Quite simply, this is a really complex maneuver and I'm not even sure how effective it would be. I mean, yes it's a cool visual but there are just so many things that could go wrong. It's not even getting into how much stress is going to be put on the weapon.
 

I agree, but that's also probably why I wouldn't allow it. Quite simply, this is a really complex maneuver and I'm not even sure how effective it would be. I mean, yes it's a cool visual but there are just so many things that could go wrong. It's not even getting into how much stress is going to be put on the weapon.
I would never say no to a really cool thing like that just because it’s improbable. Make an Acrobatics check to not eat cement, and an attack roll to make it all worth it, done. Everything else can be handwaved because we are playing a game, not trying to simulate reality.
 

I would never say no to a really cool thing like that just because it’s improbable. Make an Acrobatics check to not eat cement, and an attack roll to make it all worth it, done. Everything else can be handwaved because we are playing a game, not trying to simulate reality.

True, but the reason Superman can get away with it is because he's the man of steel. :)

I do agree that it's one of those "can I think of something simple" things. Maybe advantage on the attack but a dex save to avoid face planting. :unsure:
 

I would never say no to a really cool thing like that just because it’s improbable. Make an Acrobatics check to not eat cement, and an attack roll to make it all worth it, done. Everything else can be handwaved because we are playing a game, not trying to simulate reality.
Yeah, but this doesn't seem really cool to me, it seems confused and weird. Cool is, you're a spear-wielding fighter that's been buffed with fly, and you want to make a dive bomb charge attack for extra damage. I'm down with that... maybe make an acrobatics check, do well and get an extra d8, fail badly and hit the ground.

But the OP's scenario warps that in several perplexing ways.
 
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True, but the reason Superman can get away with it is because he's the man of steel. :)

I do agree that it's one of those "can I think of something simple" things. Maybe advantage on the attack but a dex save to avoid face planting. :unsure:
That could work, for sure. If the risk is high enough, I might make it adv and bonus damage if successful. If the target is unaware of you, absolutely adv and bonus damage.
 

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