Planning a date is hard enough. You have to book a dinner reservation far enough in advance that you’re not forced to eat in the mid-afternoon or past 10pm. And then, assuming dinner goes well, you need at least an idea of where to go afterwards - somewhere that’s close enough to walk to, has decent drinks, and ideally isn’t full of college-aged kids bragging about how good their fake IDs are.
Then winter hits, and date-planning somehow gets even harder. Mostly because the second venue has to basically be directly adjacent to the first venue to avoid hypothermia and/or frostbite. That’s why we made the One-Two Punch guide. It’s got a bunch of restaurants and bars that are, at the most, a few blocks away from each other, so that you can confidently plan a really good two-part date, regardless of the forecast.
Townsend / ITV
If this isn’t your first date and you’re looking for something a bit more upscale to impress your possible future life partner, take them to Townsend in East Passyunk. It’s two floors, with a white-tablecloth dining room upstairs that serves classic French food, like seared Hudson Valley foie gras and a 32 oz. cote de boeuf that will easily feed both of you. The downstairs bar is good for a pre-dinner drink while you wait for your table upstairs, but you have bigger plans for the end of your night.
After splitting a bottle of wine at Townsend and building a decent alcohol jacket, head a few storefronts down to ITV. This place is pretty much built for nightcaps, with dim lighting, lots of wine, and white string lights strung over the bar area. They have a full dinner menu, but you’ve already taken care of that, so stick to their cocktails, which change with the seasons and are the best in the area.
Trattoria Carina / Doobie's
In the summer, Trattoria Carina is one of the best places to eat pasta outside around Rittenhouse. But as soon as the outdoor tables are hauled off to a storage room for the winter, people seem to forget about this small Italian spot, and that might make it even better. Especially when it’s snowing outside, sitting next to the full-length windows in the warm dining room with a hot plate of pasta and a date is exactly where you want to be.
Right down the street from Trattoria Carina is Doobie’s, which is a cash-only dive that, at first glance, might not seem exactly like a great place to have a quiet post-pasta drink. But this is a place where magic happens. Not the kind of magic that Usher talks about in his 2006 episode of MTV Cribs, but the kind that turns a date from benign, polite questions about each other’s jobs to getting embarrassingly competitive over a game of Scrabble or swing dancing to whatever song is up on the jukebox.
The Good king tavern / hale & true
The words “tavern” and “date night” don’t generally go hand in hand, but that’s one of the reasons that The Good King Tavern is so great. It manages to be both casual enough to go with a few friends for a Sunday night dinner, but quiet and dark enough to be the perfect place for a mid-winter date night. Make sure to get the duck wings, but you really can’t go wrong with any of their small plates (which are called “tavern fare” on the menu).
Walk out of Good King Tavern, and look directly across South 7th street. Hale & True Cider Co. is only about 15 paces away, which means that no matter how cold it is outside, you have a very low chance of developing frostbite.* It’s a big cidery with high ceilings and a rotating selection of seasonal ciders, and while it’s not exactly the most romantic spot in the city, it does have some really interesting things on tap, like a pineapple basil cider that we’re particularly huge fans of. Also, did we mention how close it is to Good King Tavern?
*For legal reasons, we should clarify that it is still possible to develop frostbite if it’s cold enough outside. Like The Day After Tomorrow cold.
Murph's / R&D
Murph’s is the most Philadelphia place in Philadelphia. It’s really just a dive bar with a few small tables in the back and one guy cooking a ton of pasta in the kitchen. It’s definitely not the place you probably imagined yourself taking your next date, but it’s a fun option that’s definitely way different from all of the wine bars her last five Tinder dates took her to. If you do it right, your table should look like a Tetris board of pasta plates, and you should share everything - especially the lobster ravioli.
This place used to be a full restaurant with brunch and dinner service called Root, but then it closed down, brainstormed a bit, and decided to reopen as R&D doing solely what they did best the first time - cocktails. It’s much better this way, and after a heavy pasta meal surrounded by people whose ancestors have lived in Philly since the Revolutionary War, sitting at a dark two-top here with a couple of good (if a bit expensive) cocktails is the way you want to end your night.
osteria / SOUTH
If you’ve ever tried to eat around the North Broad area, you know that the list of actually good options for dinner is short. But one of those options that works especially well for a date is Osteria. This spacious Italian spot has a long bar and great covered patio, which is surrounded by glass on all sides and will let you pretend, if only for a few seconds, that you’re eating outside in the summer. The pastas and cocktails are all excellent, and we’re also big fans of the wood-grilled chicken if you want something that won’t weigh you down for the rest of the night.
Directly next to Osteria is South - a southern restaurant and jazz bar that you should come back to another night for a full dinner. But tonight, you’re here for one of their live jazz shows. Grab a couple seats at the bar, picture yourself on Bourbon Street, and enjoy one of the only places in the city that has reliable live music pretty much every night of the week.
A mano / la calaca feliz
For a date in Fairmount, you can’t do much better than A Mano. Everything they do seems effortless, from the upscale, but still somehow casual feel of the dining room to the food, which tastes like it was made in a back-alley kitchen in Florence, but looks like the stuff you’d find in the most expensive and technical restaurants in the city. There’s a lot of good pasta on this guide, but is there really any better food to eat during the winter? And when it comes to pasta, A Mano is the spot to beat.
On any other night, you might head to La Calaca Feliz for Happy Hour and some tacos, but tonight you’re here to share some post-dinner margaritas with your date. Once you’ve attacked a few of those and gotten into why each other’s previous relationships failed, maybe share a couple of late night tacos and some guacamole to sober up, before taking separate cars home and wondering why you had to talk about how your mom’s a sex therapist this early on.
Amada / sassafras
Tapas and date nights go together like citywides and not making it into work the next day, and for tapas in Old City, Amada is the only way to go. The dark Spanish spot looks kind of like a wine cellar, and on any given day, pretty much every table is a two-top hosting a couple of some sort. So, while you share a few of their small plates, some cheese, and a bottle of wine, you can play that fun game where you try to guess what stage of dating every other couple in the restaurant is in, and whether or not they’re going to make it based on snap judgments. Exhilarating stuff.
Right down the street from Amada, you’ll find a little, romantic bar called Sassafras. It looks a bit like the living room of an old, expensive (probably haunted) house, and the lighting is always dim. It’s usually pretty quiet after the dinner crowd leaves, which means you’ll probably only share the space with a couple of other people who are also using it to close out their successful date. The cocktails are decent, the beers are good, and, most importantly, you’re here because your date is clearly going about as well as could be planned. Congrats.