Go Back to Basics with this Throwback Steakhouse and Traditional Dessert

Tonight isn’t just about going upscale but back in time. Opened in 1837, Delmonico’s has hardly changed. With a lavish throwback design that harkens back to NYC’s roots, standout features at this high-end steakhouse include massive Pompeian pillars at its entrance, period-specific artwork framed along its dining room, and dark mahogany millwork heightening the overt luxury. And even though the menu is comprised mostly of steak (it is a steakhouse after all), to really seal the deal on this dining experience, order the classic baked Alaska for dessert. Created by Delmonico’s original chef Charles Ranhofer in 1867, this one’s a necessity.

For dessert, the two of you will be slipping into something decidedly more casual. Take a walk over to Insomnia Cookies and prep yourselves for something cheap and sweet. You’re welcome to their traditional cookies, but we dare you to go bolder with a cookie a la mode or one of their ice cream-filled ‘wiches. There aren’t any fancy/over-the-top flavors here; just classic options that are tried and true—which is basically their general hook as these cookies are so good that they don’t require any additional pizazz.