Planning a date in New York is a logistical nightmare. You’re picking a semi-convenient neighborhood, choosing one of 20,000 businesses in that vicinity to give your patronage, making sure you can actually get into said business, and hoping it isn’t terrible or $700.
Historically, this has been the request that comes to me most often—friends looking for the best date spots, usually in the West Village or somewhere around that latitude. This is, in my opinion, one of the more difficult requests to fulfill, not because I don’t have a long list of date night spots to share, but because in order to give my best suggestions I would need answers to several follow-up questions. Are we going for easy and calm or are we going for dimly-lit and sexy? Is the priority dinner, drinks, or both? Are you planning ahead or is this for two days from now? Ambience and preferred food quantity are both key considerations in picking a location for a date, though the scheduling component is often the deciding factor as New York’s dining landscape builds on scarcity and exclusivity (did we all see the article about the college grad who is flipping reservations like they’re sneakers, and making a killing doing so??)
The spots that follow are my favorite date night recs—whether it’s a first date and you are treading the age-old dilemma of wanting to impress without being overzealous, or you and your partner are looking for a new special occasion spot for any old Friday night. Enjoy!
Penny
When one of your favorite restaurants opens a new spot, there is cause for celebration. It is especially thrilling when said spot is your favorite outing of the entire year (so far—it’s only April but still!). Claud outdid itself with Penny, which Hallie and I went to on its opening night, having scored a reservation weeks in advance. Penny is just a really good time. The slender space is filled with two long counters facing the chefs as they work their magic crafting your meals, and is run by the kindest staff I have ever met. Hallie and I made at least four friends during our meal there. As far as date set-up, Penny is not overly dark and intimate, though the space is so small there is definitely a sense of coziness, both in proximity to chef and neighboring patrons. I also love the set-up, a counter can seem casual, but side-by-side stools are my preferred seating arrangement, especially on a date. I always want to sit at the bar. Tables feel weird for some reason?
As expected from a Claud relative, the wine at Penny was exceptional which, as a through-line in this newsletter, is my preferred beverage on a date. It is sophisticated and fun and you don’t have to stress about what cocktail you’ll order, what liquor you’re committing to, or how strong the drink will be. With the seafood element and the promise of an exquisite meal, a glass (or two) of wine was the perfect supplement.
Starting from the top, we ordered the house made sesame brioche served with a smattering of salted butter which we obviously added anchovies to. The bread came out warm from a very cute oven right in front of us, and was like eating a dreamy salty cloud. We fully considered ordering a second loaf (albeit a mini one) for mid way through the meal because the first one went so quickly. This is potentially tied with Four Horseman for best bread service in New York. We followed with the Ice Box, a very fresh and very cold tray of all the best things, including an incredible tartare. Not all shrimp cocktail are created equal and these were spectacular—not a bite on this tray was consumed passively and was the ideal amount to share for two. We got a beautifully smoky octopus and potato salad which felt like a surprising pairing turned match made in heaven. The soft and creamy potato with the bite of the octopus was to die for, garnished with a flurry of paprika and smoked daikon radish. We also initially didn’t order this and then I kept seeing them walk them to other guests and decided I needed it which, it turns out, I definitely did. The stuffed squid was memorable, filled with a mix of swiss chard and tuna, grilled and coated with a harissa oil. This is hard to describe and is something you have to try for yourself, but was decidedly the best thing I ate all night. We got the dover sole with a bone marrow wine sauce and pickled mushrooms that rivaled the dover sole at Claud (shocking, honestly) and finally, the dish that will certainly put Penny all over your Instagram—the ice cream sandwich. Sitting between two slices of brioche (genius) is vanilla ice cream, jam, and salted strawberries. It is soft and sweet, distinctly not messy, and made us all think really deeply about why this isn’t common practice.
Penny is special, their team is incredible, the food is amazing, and it isn’t fancy or pretentious. It is just really good. While the wait time is sure to get increasingly hectic, the mostly walk-in only policy makes for good last minute planning. But if you are banking on a seat… go as early as you can.
*Penny has very limited reservations that open a week in advance. The counter is mostly reserved for walk-ins!*
Gem Wine
Gem Wine is a special place. Formerly a 20-ish seat, very cozy space, they have upgraded to the former Gem space to expand their seating capacity. Often full, very lively, and a generally great time, Gem is an easy, laid-back, occasionally scene-y date spot. The focus here is really the wine list which their staff will more than willingly guide you through, though their food menu offers a pretty perfect assortment of plates to accompany your orange wine ranging from their gouda plate (which is a MUST, especially during cherry season), to skate wing and very cute desserts. They have celery root ice cream on right now which I am very into the idea of.
The space feels like the living room of your chic rich aunt who throws great parties. The guests are often in the late-20s to mid-40s range and the staff err on the younger side, so on a Saturday night it can feel like quite a scene. It is definitely on the sexier, more romantic side, and is much less formal than the prior suggestion in that it is technically a wine bar, rather than a full-blown restaurant. In my mind, this is the ultimate “oh, this old thing?” spot—guaranteed to impress in a very much not-trying way. The best part is, between Gem Wine and Gem House, they often host really incredible residencies of different chefs, the most recent being my immaculate dinner from Ha’s Dac Biet!! That is always a fun, thoughtful, special occasion outing. More pics from that dinner on Instagram.
*Reservations open a month out, and though not fully necessary, the wait without one might be 90 minutes on a weekend.*
Demo
Okay, 3/3 downtown wine bars, Demo gets extra points for being newly opened and already a hotspot, which bodes well for a date-planner! I have actually heard mixed reviews of Demo, but I personally had an incredibly meal here and look forward to going back. Demo is the darkest, moodiest, and most intimate of the spots mentioned. When you walk in, you really feel like it’s date-night and will probably be eating next to a lot of other couples. With a luxurious menu and a long wine list that is fun to pick through and pretend you really know what you’re talking about, Demo is a great pick for when you want to up-the-ante a bit.
We started with a mystery-allium focaccia with both butter and oil (duh), followed by a chopped Radicchio salad with a creamy tahini dressing, shaved fennel, and a za’atar breadcrumb on top. This salad was very, very good and very, very simple. Pictured below is the sorana bean dish with green chickpeas, which I have been seeing on a lot of menus lately, and fava beans. This dish was served cold and in a broth made from charred fava husks—it was very light, an important addition to an otherwise rich meal. I also really love a new, interesting bean dish and this one was quite nice. The star of the show was, without a doubt, Lobster Au Poivre. This was stupid it was so good. The lobster was incredibly tender, de-shelled and swimming in a beautiful au poivre sauce. The dish was so buttery and peppery and filling. It also came with McDonalds-esque French fries that were well-salted, well-fried, and the perfect vehicle for consuming as much of that sauce as possible. We finished with the English Pea pavlova, served with strawberry rhubarb jam and salted sesame cream. I was obsessed with this dessert, as I am often am with dishes involving meringue. It was springy, light, tart, sweet, and salty all at once! What more could you ever wish for.
This was a good meal with very good wine in a very nice setting. Would certainly recommend taking your honey… or for a solo date night… I am pro taking yourself out to dinner.
Where to next??
Oh, I’ve wanted to try Penny!! The dessert at Demo was amazing but didn’t love the vibe. I’m excited to return to Peasant for an Autumn date night, too!