Crumbled cookies and gelatin sounds like one of those things that could either be awesome, or incredibly disgusting.
Of course, I was only recently introduced to a dessert that combines gelatin with pretzels (plus a ridiculous amount of butter) to surprisingly good effect, so I suppose you never know until you try.
Seems to me that the best idea would be to bake the cookies without chocolate chips and then line the inside with a layer of melted chocolate, reinforcing the cookie and providing a sealant (and waterproofing) to hold the milk.
Technically, isnât this âmilkproofingâ? (ducks, runs away)
If youâre going to be picky - itâs still WATERproofing because itâs not the fat, protein or minerals in the milk which would cause the cookie to become soggy and fall apart. 
The main reason for avoiding plain chocolate as a lining is that the âofficialâ ones are intended to be served warmed from a hotbox, with the chocolate chips gooey. Chocolate lining would get all melty under those conditions as well, and could end up with a failing seal.
If youâre just intending to eat the whole thing cold, though, the chocolate lining would be fine.
Ah, I see. That seems like it would run into a problem similar to what the old âMcDLTâ was designed to get around, though. I totally understand wanting a warm cookie with melty chocolate - but you then want ice cold milk to go with that. Pouring cold milk into a hot cookie cup is going to pretty rapidly move toward temperature equilibrium and tepid milk with cookie just doesnât sound appealing to me.
Of course - to me, the only time milk for drinking should be warm (or hot) is if itâs being made into cocoa.
From the SeriousEats review (linked in the previous BB post about these), somebody asked, and hereâs what the response was (from the SeriousEats reviewer):
Itâs close to a standard glaze like from a doughnut with a little more real chocolate. It can therefore withstand the mild heat from a hot box (not an over) much better than the 60-70% chocolate which is nearly half fat by weight. Glaze has almost no fat. Itâs not waxy at all. When asked directly about coating, the person who accompanied me said she didnât even notice the glaze and I agree with that assessment.
Incidentally, the comments on that SeriousEats review are quite hilarious.
Well, on the plus side, if you used the chocolate lining youâd start getting chocolate milk. 
I have to wonder what these cookie cups would be like with shots of Godivaâs chocolate liqueurs.
[edit] I had to look up the McDLT⌠found it at http://listverse.com/2009/05/30/top-10-failed-mcdonalds-products/ . Wow. The obvious issue would be that there is NO way the toppings would stay in a nice, neat pile like that with any sort of jostling.
Two words: ice cream. 
That was actually one of the better products McDonaldâs ever had. It worked really well to keep the toppings crisp. However, it used twice as much styrofoam and there was major outrage about that.
In the picture before SXSW, I thought these were lined with chocolate. You know, melt a Scharffenbergerâs dark chocolate bar, pour into the cup, swirl it around, put upside-down on cooling rack so the excess drips out to be used again⌠Or eaten, as a ganache poster suggests.
Oh man⌠McDonaldâs pizza! I used to LOVE those! The reason I stopped ordering them, though, was because they took FOR GOD DAMNED EVER to cook if there werenât any fresh ones waiting (which there never was, because nobody ever ordered them). Ok, more like 10 minutes⌠But thatâs a hell of a long time to wait for McDonaldâs food when all your friends are already eating their burgers.
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