all out date night in midtown manhattan

We often treat double date night with friends as an excuse to hit up not one but two places. Manhattan has so many great spots that you’re never at a loss for a second stop!

To start, we made our way to Raines Law Room at The William. This location has a different vibe from the original location in the Flatiron District; that one a true speakeasy, whereas this one has more of an upscale hotel cocktail bar vibe. They each accept reservations – (Sunday through Tuesday in the Flatiron, Monday through Saturday in Midtown). Both also have the same great menu, featuring a number of familiar dishes, some Raines standards, and several seasonal offerings. There are also a limited number of nibbles and desserts. If you’re there, I recommend their ricotta and toast. Delicious.

For cocktails, it’s hard to go wrong. I tried their Ol’ Pepper: rye whiskey, lemon, chipotle honey, and Worcestershire sauce, shaken and served on a rock. Unique and worth a try, though I’d recommend requesting they go light on the Worcestershire. They also do a solid penicillin, a cocktail that’s a mix of scotch, honey, ginger, and Laphroaig – a very specific Islay scotch known for its peaty flavor. It’s a staple that became popular in the mid-2000’s speakeasy surge. It’s not technically on the menu, but they’ll whip one up if you ask.

We didn’t want to ruin our appetites, because we were en route to the second reservation of the evening: just a bit around the corner to Zengo, one of Richard Sandoval’s restaurants. I’d been to the DC location years ago, and remembered finding it quite good. It’s an interesting mix; they dub the cuisine as an “artful blend of Latin-Asian styles and flavor.”

To start, we ordered their short rib “coca” (Spanish flatbread). I thought it sounded great, but was still surprised to find it was one of the stars of the night. Braised short rib, manchego cheese, and arugula, all drizzled with horseradish crema. They didn’t skimp on meat or the overall portion size. At $14, it was a good deal for an appetizer.

Of the mains we tried, the winner was the chili crab “Hong Kong” noodle: crispy noodles, sugar snap peas, asparagus, egg, and a spicy curry. Not quite ready to let he flavor of crabs go, I found this a perfect spicy cold weather dish.

We will definitely be back to try out their brunch extravaganza, which features unlimited small plates.

Overall, these two spots made for a perfect night out with friends. We all agreed that the intimate space at Raines made for a perfect first location, rather than fighting the loud post-happy hour crowd at most bars. By the time we made it to Zengo, the dinner rush had passed, which made it easier for us to continue our conversation there.

Raines Law Room – 24 East 39th Street
Reservations Suggested

Zengo – 622 Third Ave (at East 40th Street) – 212.808.8110
Reservations Suggested