Edit 3: I'm leaving now, full updates should be around 8-8:30 EST if things go according to plan.
Edit 4: FLAWLESS VICTORY
I went and picked her up at her place, purposefully leaving late so it wouldn't make sense for me to park, go in (she lives in a condo complex), go down to the garage to get her car, etc.
Got there, I had the sense to sit on the side of the booth facing the door so her back was to it.
I ordered the Alaskan Halibut special ($20), some bang-bang shrimp as an appetizer ($9), and two New Castles ($4.50 each), she had a $19 steak and a coke (who knows?), for a grand total of $57 + her soda, tax, and tip.
Ate my meal, which was quite delicious. Finished and did the "I have to pee routine". Got up and went behind a wall and flagged down the waiter. Asked him to "do me a huge favor" and told him it was mine and her 1 year anniversary and I needed him to hand her this card, and as he was doing it I was gonna walk around the other side of the restaraunt and sneak out to set something up I had planned outside. He was TOTALLY into it (young guy) and thought it was a cool move as her bf ()
He did it perfectly, distracting her with small talk...and while running out I snapped this prize pic: