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The grappling rules sure are... light. Supposing one has an Extra Attack:

  • Assuming one has successfully grappled an opponent with one's first attack, can one then perform a normal attack action with one's Extra Attack? Against the grappled opponent or any opponent within reach? Limitations on weapons (e.g. one-handed only)?

  • Assuming one has successfully grappled an opponent with one's first attack, can one's grappled opponent (now with move 0) perform a normal attack action? Against you or against any one in reach?

  • Do advantage and disadvantage (along the lines of restraint) come into play?

  • Are there grappling-specific attacks for damage (e.g. choke-hold)?

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To the first question. Yes, "If you're able to make multiple attacks with the Attack action, this attack replaces one of them." (PHB 195) So yes you can attack again if you grapple with your first action. You are not limited to whom you attack, so anyone in reach including the grappled opponent is fine.

Your opponent is only frozen in place. That is the only restriction. He can attack you or anyone else if they are within his reach.

Advantage and Disadvantage work as normal, but nothing special is added due to the grapple.

Not at this time, unless you have a specific spell or class feature that grants them. For instance the Grappler feat adds additional things to do with the Grappled condition, such as adding restrained.

So basically, as a part of your attack action, you can grab someone, all this does is set their speed to 0. That's pretty much it. There are other things you can do, but it's largely dependent on having class features or feats to support it. The WOTC forums have a lot more information in the Grappler's Guide that Ruut pointed to in his answer.

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  • \$\begingroup\$ If a DM failed to penalize a grappled opponent's actions due to the grapple, and tried justifying it by saying that the rules only provide for freezing him in place, I'd seriously consider walking. \$\endgroup\$ – Smithers Oct 18 '14 at 19:35
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    \$\begingroup\$ @Smithers Perhaps this would be a better topic for chat? chat.stackexchange.com/rooms/15929/dd-5e-debate-room \$\endgroup\$ – wax eagle Oct 19 '14 at 0:49
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To grapple someone, you need a hand dedicated to it. Otherwise, there aren't any restrictions about attacks. Yes, you can Attack them. Yes, they can Attack you or someone else nearby.

Think of it like you grabbed them by the shoulder. They can't move away unless they can shake you off, but otherwise they can act normally.

Advantage / disadvantage doesn't automatically factor in. There aren't any special moves except the Grappler feat (which lets you restrain them, which can also be fun and grant advantage).

One great way to gain advantage is to grapple them and then shove them prone, which is useful because:

  • Being prone, they have disadvantage with their attacks. Any attacks made against them from within 5 ft have advantage. Attacks made against them from further than 5 ft have disadvantage.
  • Being prone, they can get up with half their movement, except...
  • Being grappled, they have no movement

So assuming you can grab 'em and knock 'em to the floor (which, yes, would be 2 attacks), they have to escape your grapple or they're well and truly hosed.

See also my question: Does Grappling in D&D 5 have any rules other than preventing movement?

Also here are a ton of fine details: http://community.wizards.com/forum/player-help/threads/4142801

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