Take her to lunch at the Boat Basin, where the food is no-frills (think standard-issue burgers and fries) but the gorgeous Hudson river views make your frozen piña colada something worth reveling in.
After your riverside snack, walk down to Pier 72 (West 72nd Street), where you and your slightly tipsy date can try your hand at kayaking on the Hudson free of charge. Thanks, Bloomberg! And if we may, a word of wisdom: If you've never had your way with a paddle before, we suggest drinking after, not before, and taking the complimentary kayaking class before heading out.
After you've tackled tandem paddling, take in the Hudson vistas as the sun sets and amble down to romantically-inclined (as in, super dark and cozy) Casellula (401 West 52nd Street), where you'll find a carefully curated selection of cheese and wine to satisfy your insatiable post-kayaking appetites.