Steaks — New York Strip is what we used, but ribeye is also an excellent and flavorful choice.
Cracked black pepper
Oil — Pick a neutral oil with a high smoke point. Canola is the best low-cost option. If you have the cash and the inclination, pick up grapeseed. Avoid olive oil, which burns easily.
Rosemary — Fresh.
To begin prep, make sure your steaks are thawed and then slap them down onto a cutting board. To ensure a proper sear and a gloriously crispy crust, pat down with a paper towel until they are as dry as possible.
Salt heavily — and don’t be shy about it. A more-than-generous pinch of kosher salt on both sides should do the trick. Sea salt is a little stronger, so if you’re using that, reduce the size of your pinch a little or ask someone with smaller hands to assist. Hit both sides with five or six turns of the pepper grinder.
Next, crack open the bottle of port. Pour yourself a glass. After that, pour your date a glass. Throw on Kamasi Washington and chat for an hour while the steaks rest.
This hour is important; you’re letting the steaks approach room temperature and giving them time to absorb all that salt, further improving the quality of the sear. Make sure to conserve at least a half cup of port for the reduction.
When there is a lull in the conversation, begin mincing your shallot and about two tablespoons worth of rosemary. If you were a line cook in a past life (or you are one now), take this time to quietly show off. If you’re a college student, offer your date a second knife and laugh while you learn to cut aromatics together. Coarsely chop up about an ounce and a half of the chocolate.
At this point, the steaks should have had almost an hour to rest. Barely cover the bottom of the pan with oil, set the burner on high and — I cannot stress this enough — turn your vent fan on. Nothing says seduction quite like wildly swinging last month’s copy of The Atlantic at a screaming fire alarm while the kitchen fills with smoke and the sad smell of culinary overreach.
At the precise moment the oil begins smoking, use tongs to lay the steaks down in the pan. There will be some splatter. Remain calm, work slowly, and you’ll minimize the mess as well as any burns.
Drop the heat slightly, just to medium-high. Do not touch the steaks for three to four minutes. Doing so will interrupt the sear that you spent that whole lazy hour prepping for. Carefully flip the steaks and admire your golden-brown handiwork.
Wait for three to four more minutes and then take the steaks out of the pan. Rest them on a cutting board and plop a knob of butter and sprig of rosemary on top of each.
Finally, lower the burner to just below medium in anticipation of…
Deglaze the pan with about half a cup of port — less if your steaks are small. Scrape the bottom of the pan with a wooden spoon, making sure to loosen up all of that precious beef fond. Throw in your minced shallot and stir in two tablespoons of balsamic vinegar.
Let the port reduce for a few minutes to half its original volume. Sometime during this time, toss in the rosemary and stir.
Once the port has reduced, stir in the ounce of chocolate, chunk by chunk until it is fully melted. Full disclosure: I used an ounce and a half because I’m a glutton. It tasted excellent. Add a few tablespoons of butter to finish the job and stir until integrated. Taste and season as needed with salt and pepper.
Slice your rested steak and spoon the sauce over top, making sure to build an appealing little mound of shallots.
Drink the rest of the port. Serve steak alongside scrumptious glazed carrots.