Some things make for better targets for grapple attempts than others.

Little Tricky Things

These are the characteristics that make an opponent a more appealing target for a grapple:

• Smaller than you

  You get a size bonus that is better than your opponent, therefore you are more likely to succeed

• Wields a two-handed weapon

  Your opponent cannot use the bulky weapon while grappled

• Uses Somatic-component spells often

  Grappling severely impairs the ability to cast these spells.

• Is wearing bulky armor

  “heavy” armor types are useless against grapple attempts, and limit your opponent’s dexterity. Most touch-attacks (such as initiating a grapple) against people in full plate mail are against an AC of 10

• Is capable of tying up multiple party members by itself

  Monsters that can fight toe-to-toe with multiple members of a party all at once competantly (due to high hit points, excellent AC, or other factors) can be made far less effective by grappling. This allows the rest of your party to deal with other matters at hand.

Big Huge Brutish Things

There are a similar number of characteristics that make an opponent an unappealing target for grappling. Here are a few (you’ll run into others yourself along the way):

• Is unimportant

  When fighting a Dracolich, an accomplished Blackguard, five trolls and a lvl1 fighter kobald, you’d better have a compelling reason to tie yourself up grappling with the kobald. There are bigger fish to fry sometimes. Always remember that in a way, initiating a grapple takes you out of combat too

• One of several capable opponents

  being tied up in a grapple while surrounded by worthwhile enemies is a bad situation to be in. That’s why you grapple, to put THEM in this bad situation. If your comrades cannot tie up the rest of the baddies, don’t grapple.

• Has tentacles

  Just about anything with tentacles is likely to be four times as good at grappling as you are. That’s what tentacles are made for, after all.

• Can fit you in its mouth

  if your opponent could fit you inside of its mouth and eat you without ripping you to shreds first, that may be exactly what it will do if you grapple with it. If this is the case and the creature also has tentacles, you may wish to consider avoiding melee entirely.

• Has a light weapon

  if your foe will still be able to attack you with its favorite weapon, grappling loses a lot of its oomph. Save grappling for the heavy weapon types or spellcasters with staves. They’ll have to fall back on a backup weapon to even start to deal with you well.

• Is clearly much stronger than you

  please don’t initiate a grapple then end up pinned yourself. It’s an embarrassment to your fellows.

• You are low on hit points

  grappling makes you a sitting duck. If you can’t suck a hit or two without going unconscious, grappling will have the be saved for another day.

This is by no means a complete list, just a number of things to take into account when determining whether initiating a grapple is the right choice at the moment. Note that there are many negative circumstances compared to the positives. This isn’t Street Fighter, so you won’t always be able to be Zalbag effectively.