Grapple is a multi-stage process. First, you try to grab your opponent. Then you attempt to hold your opponent. If you establish a hold, you have options for what you can do next (including potentially dealing damage to or pinning your opponent). Third, you can attempt to maintain the grapple, which entails moving into the target's square (difficult here since there's a wall and a window separating T-dawg and the boy).
To initiate a grab, have T-dawg roll a grapple check against the lad's AC 12/ This will be a melee touch attack (base attack bonus + Strength modifier). There isn't an additional grapple modifier that will apply in this situation because both T-dawg and the lad are the same size (medium). If the grab is successful, T-dawg would then try to hold the lad by making an opposed grapple check as a free action (again, base attack bonus + Strength modifier).
I do not see an Improved Grapple feat in the hardcover, and nothing in the section in the hardcover on Grapple leads me to believe T-dawg will suffer a -4 penalty to his grapple check. The attempt will, however, provoke an AoO from the teen. Also, it's my contention that T-dawg's Brawl feat should apply to grant him +1 to his grapple check.
Basically, it's kinda-sorta like a 5e attack with disadvantage.
"Come 'ere you", T-dawg grunts as he reaches through the window to grab the teen and pull him through into the kitchen.
OOC:
Ok, here you go, three rolls, first touch attack, then opposed grapple, then roll to maintain (I've pre-spent APs for convenience, not sure if I get a "refund" on the unneeded ones or not - I probably wouldn't have bothered on the touch attack with a 17 total, but will on both the grapple checks having seen those rolls) _: 1D20+7+1D6 = [10]+7+[2] = 19
1D20+7+1D6 = [7]+7+[3] = 17
1D20+7+1D6 = [2]+7+[3] = 12
On reflection, I'll also take a free action to use his "Ability Surge" class feature, which will give him +4 Str for another +2 bonus for 2 rounds (long enough to apply to all three checks, correct?), so the totals are 21/19/14 respectively. Finally, I'll spend a further action point to negate the fatigued penalty he'd normally get from Action Surge.
If successful, given the difference in size/Str can I attempt to maintain the grapple by moving him into my square (i.e.: dragging him through the window), rather than moving into his square?
I think the quotation marks are screwing the roller up. Easiest way would be to put the description outside of the [ roll ] instructions. Like:
Attack = [roll0]
Yeah, tried with and without the quotes, no dice. didn't try with the description outside the roll tags... I'll give it a test in the OOC thread to not mess this thread up further.
Forged Fury asked whether you can take an AoO in 3.x if you're unarmed. The answer is no (Hardcover, pp 138). I'm unclear why you're asking, FF. Let me know. T-dawg doesn't have the Combat Martial Arts feat that I was hoping he would take when we leveled up, which would've made his unarmed attacks count as armed, but it's the lad who gets the AoO. Unless I'm missing something else?
I still want to grant T-dawg the +1 from Brawl; Brawl applies to any unarmed attack, armed or otherwise, and I think it's reasonable to apply it to the grapple check. If someone strenuously objects to the +1 from Brawl, we can after-action review this encounter in the OOC, but for now I want to push forward. [MENTION=12430]gribble[/MENTION], I think you only really need to spend one Action Point to accomplish what you want to do.
T-dawg reached out through the window and grabbed hold of the boy's leather jacket sleeve. There was a hiss, then something sharp glanced against T-dawg's forearm. By the feel of it, the boy tried to knife T-dawg's forearm, but missed. The boy started struggling against T-dawg's grip on his jacket, but the struggle was in vain; T-dawg shored up his hold on the boy's wrist and refused to let go.
Just then, however, the quiet click of a gun's safety being switched off sounded from the open kitchen doorway. T-dawg looked up and saw a second figure, a girl aged maybe 18 or 19, standing in the doorway. She was fifteen feet away and had what he recognized (thanks to his training yesterday) as a Derringer .45 trained on him. "Let him go. Then back away real slow, mister." The girl was nervous. Her hand shook, and her voice wavered.