I spent some time today (about two hours) analyzing the entire "grapple" process and it seems to me that the trouble with the rules isn't that they are too complex. The real trouble is, and this is the problem with the vast majority of D&D, is that they are grossly verbose. It seems to me that the rules are just packed with too much text. Previous editions of D&D used more tables to elucidate the rules or provide for quick reference. I've taken a page from that book here.
Anyway, fellow gamers, we're not dummies. The details of grappling are just buried in too much branching conditional text. Being a programmer myself, I attempted to provide a more programmatic version or summary of the rules for quick reference in our games. Below are the results of this quest from our house rules.
Finally, The good thing about the original grapple rules is that they are a good simulation of what could actually happen in a real hand-to-hand fight. They even cover the rather dramatic case of turning an enemy's weapon against him and stabbing him with it. By the way I prefer the term "wrestling" since grappling can refer to the use of a hook like device for scaling walls. 
So here goes...
P.S. These rules will look better in Internet Explorer than in Firefox since I used Word 2007 to create the original document. Please don't sue me.
Purpose: Use hand-to-hand combat and wrestling maneuvers to hold, break a hold, or capture an enemy.
Restrictions: Here they are:
P You threaten no squares while grappling.
P You lose your Dexterity bonus to AC against enemies you aren't grappling.
P In general, your hands are busy.
v Step 1: If you have Improved Grapple, skip to Step 3.
P You cannot grapple an enemy more the one step away from your own size category.
v Step 2: You provoke an attack of opportunity from the enemy you're trying to grapple.
P You fail the grapple attempt if your enemy's attack deals damage.
P You may try again if you have multiple attacks, at a reduced base attack bonus.
v Step 3: Make a melee attack roll (Base attack bonus + Strength modifier + size modifier) against your enemy's touch AC.
P If you hit you can proceed with the grapple attempt. Go to Step 4.
P If you miss the grapple attempt fails.
v Step 4: Make an opposed grapple check as a free action.
P If you win you deal 1d3 non-lethal damage (1d2 if you're Small; you do more damage if you're a monk). Go to Step 5.
P If you fail the grapple attempt fails.
v Step 5: Move into the enemy's square as a free action if you wish to maintain a hold. If you cannot move the grapple ends and you let go.
P Your movement provokes an attack of opportunity from your enemy's allies.
v Step 6: Consult optional actions below for additional actions during a grapple.
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Optional Grapple Actions
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Action
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Action
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Conditions
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Check
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Damage or Result
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Attack, Natural Weapon
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Standard
(Attack)
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-
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Atk -4
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Per creature attack damage
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Attack, Unarmed
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Standard
(Attack)
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-
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Atk -4
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1d3 non-lethal damage (Medium)
1d2 non-lethal damage (Small)
Note: Monks do more damage.
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Attack, Use Enemy Weapon
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Standard
(Attack)
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w Light weapon only
w Enemy keeps his weapon
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Opposed grapple and Atk -4
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Per light weapon damage
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Attack, Weapon
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Standard
(Attack)
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w Light weapon only
w No two-weapon fighting allowed
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Atk -4
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Per light weapon damage
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Cast Spell
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Standard
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w As standard action casting only
w Must have components/focus in hand
w Spell has no somatic components
w No spells that require complex activity
Note: Still applies even if you're pinned
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Concentration DC 20 + spell level or spell is lost
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Per spell damage (if any)
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Damage Enemy, Beat
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Standard
(Attack)
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-
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Opposed grapple
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1d3 non-lethal damage (Medium)
1d2 non-lethal damage (Small)
Note: Monks do more damage.
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Damage Enemy, Harm
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Standard
(Attack)
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-
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Opposed grapple -4
Note: No penalty for monks.
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1d3 lethal damage (Medium)
1d2 lethal damage (Small)
Note: Monks do more damage.
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Draw Weapon, Light
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Move
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-
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Grapple check DC 15
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Weapon drawn
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Draw Weapon, Quick
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Free or
Move
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w Quick Draw feat
w Drawing hidden weapon: move action
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Grapple check DC 10 or
Grapple check DC 15 (Hidden)
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Weapon drawn
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Escape, Escape Artist
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Standard (Attack)
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w Grappled only (see Pinned below)
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Skill check
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You escape
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Escape, Grapple
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Standard
(Attack)
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w Grappled only (see Pinned below)
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Opposed grapple (each grappler)
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You escape
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Join Grapple
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Standard
(Attack)
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w Enemy gets no attack of opportunity
w You succeed on the melee touch attack automatically
w Limit four grapplers of the same size category. Creatures one size category down count as half (1/2) toward the limit, while one size category up counts as double (x2).
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Opposed grapple (single enemy)
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-
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Move, Half
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Move
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w Grappler moves with you
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Opposed grapple (each grappler) or opposed grapple +4 against a single pinned opponent
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-
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Pinned, Self
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Lose Turn
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w For 1 round only
w AC -4 for non-grappling enemies
w You may be unable to speak
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None
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Immobilized and/or unable to speak
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Pinning, Enemy
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Standard
(Attack)
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w Pins enemy for 1 round only
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Opposed grapple
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Enemy immobilized or...
Additional Options:
w Stop enemy from speaking (free action
w Disarm (Enemy resists +4)
w Snatch (Enemy resists +4)
w Release pin, grapple or both (free action)
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Retrieve Pouch Item
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Full
Round
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Note: For example, material component
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-
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-
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Unpin, Friend
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Standard
(Attack)
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-
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Opposed grapple
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Removes pinned condition
Friend is still grappling
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Use Magic Item
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Standard
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No spell completion trigger
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-
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Per magic item (if any)
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