The Thing
Attacking with a melee weapon in to a grapple is more a matter of luck than skill, as there is an equal chance of hitting each grappling combatant. When we were attacking the grapple-happy Marrowbreakers we had to check to see if we hadn't hit an ally by mistake. With Tal in a grapple the DM had many occasion to ask us to 'Roll to see if you hit the Marrowbreaker or Tal.'
'Okay, if I roll high I hit it', or, 'if I roll high I hit the monster', came the reply.
In each case we had to clarify 'Who do you mean, Tal or the Marrowbreaker?' and there was much rejoicing. This probably irked Tal a bit, and if it didn't we must have pushed him over the edge when the second Marrowbreaker grappled with Dexter.
'Roll to see if you hit the Marrowbreaker or Dexter.'
'Okay, if I roll high I hit it.' <rolls die>
'... Wait, aren't you going to ask who he means?' asks Tal.
'Nope, it's pretty clear he means the Marrowbreaker to me.'
7th May 2008 at 12.50 pm
You should re-read that section on grapple because melee attacks do not face that random chance of clobbering either target (unless you've agreed on that as a house rule). Only range attacks suffer that risk...
http://www.d20srd.org/srd/combat/specialAttacks.htm#grapple
Also look at the table on the right side of this page:
http://www.d20srd.org/srd/combat/combatModifiers.htm
Across the row of "Grappling (but attacker is not)" you'll see two columns, one for melee and one for ranged attacks. Note only the ranged attack column has footnote 3 which states there is a random chance of hitting either target.
Melee weapons are closer in and you can time them easier. ;)
(That chart and footnote is also in the PHB)
7th May 2008 at 5.11 pm
That's certainly true in 3.5e D&D, but we're currently playing with the Iron Heroes variant PHB. The grapple rules are changed so that attacking in to a grapple, even with melee, hits a random combatant in the grapple.
It makes a little sense, but unfortunately it tends to negate all the interesting aspects of Iron Heroes combat, like stunts and challenges. It also makes it almost impossible to defeat opponents who have some form of the Improved Grapple feat, as we found out when tackling the Marrowbreakers. Not being able to break the grapple, attack your opponent, or draw a light weapon makes being grappled too difficult, meanwhile attacking from outside the grapple means you cannot do sneak attack damage, and you risk hurting an ally with each attack.
The sooner we get past all the grappling monsters the better. Fourth edition D&D will be out by then though.