SIZZLE & SCORE
WHEN THE GAME IS ON THE LINE
S&S GAME PLAN

Rosemary Red Wine
Flank Steak

with Baked Parmesan Risotto & Roasted Asparagus

Rosemary red wine marinated flank steak grilled hot and sliced thin, creamy Parmesan risotto without babysitting the stove, and simple roasted asparagus. Steak night without steakhouse-level stress.

Rosemary Red Wine Flank Steak with Parmesan risotto and roasted asparagus on a Southwest patio date night
♨
SERVES
2
◷
PREP
20 MIN
♨
COOK
45 MIN
★
DIFFICULTY
★★☆☆☆

WHAT YOU’RE MAKING

Rosemary Red Wine
Flank Steak
Baked
Parmesan Risotto
Roasted
Asparagus

THE DRINKS

Rosemary Bourbon Smash

PER PERSON
2 oz bourbon
¾ oz fresh lemon juice
½ oz simple syrup
1 fresh rosemary sprig
Ice
Add the bourbon, lemon juice and simple syrup to a shaker filled with ice. Shake hard for 10–15 seconds, then strain into a rocks glass over fresh ice. Give the rosemary sprig a firm smack between your palms and drop it into the glass.
Learning Point — Wake Up The Rosemary Smacking the rosemary releases the aromatic oils in the leaves. You taste with your nose too, so that fresh rosemary hits you every time you bring the glass up for a sip. Smack it. Don’t pulverize it. We’re making a cocktail, not disciplining a houseplant.

WHAT YOU NEED

Rosemary Red Wine Flank Steak

  • 1½–2 lb flank steak
  • ½ cup olive oil
  • 1½ cups red wine
  • ¼ cup soy sauce
  • 2 Tbsp Worcestershire sauce
  • 2 Tbsp fresh rosemary, chopped
  • 4 garlic cloves, smashed
  • Salt + black pepper, to taste
S&S Rule — Fresh Rosemary
Fresh rosemary. Not dried. This is not the place to raid the spice cabinet.

Baked Parmesan Risotto

  • 1 cup Arborio rice
  • 2½ cups chicken broth
  • Extra broth for finishing, if needed
  • 1 small shallot, finely chopped
  • 1 garlic clove, minced
  • 2 Tbsp butter, divided
  • ½ cup freshly grated Parmesan
  • Salt + black pepper, to taste

Roasted Asparagus

  • 1 bunch asparagus
  • 1 Tbsp olive oil
  • ½ tsp kosher salt
  • ¼ tsp black pepper

Gear

  • Grill
  • Oven-safe pot with lid
  • Sheet pan
  • Instant-read meat thermometer
  • Cutting board
  • Sharp chef’s knife
  • Tongs
  • Cocktail shaker
  • Rocks glasses

BEFORE SHE GETS THERE

  • GIVE THE STEAK ITS FOUR HOURS.
    That rosemary red wine marinade needs time to do its thing. Get the flank steak in early and leave it alone.
  • CLEAR THE RUNWAY.
    Trim the asparagus, chop the shallot and garlic, grate the Parmesan, and have your cooking ingredients ready to grab. Once the night starts, nobody wants to watch you hunt for a cheese grater.
  • MAKE THE TABLE LOOK INTENTIONAL.
    Two plates. Two glasses. Silverware. Napkins. Maybe a candle. Five minutes of effort makes it look like you actually planned this.
  • BUILD THE BAR BEFORE YOU NEED IT.
    Bourbon, lemons, simple syrup, rosemary and ice ready to go. When she gets there, making the first drink should be easy.
  • CHANGE THE ROOM.
    Kill the overhead lights. Put some music on. Straighten up anything that screams Tuesday night eating dinner on the couch.
  • RESET THE KITCHEN.
    Prep mess gone. Sink empty. Counters wiped. Trash handled.
You already did the work.
Now make it look effortless.

PLAY BY PLAY

  1. GET THE STEAK OUT
    About 30 minutes before you plan to grill, pull the 1½–2 lb flank steak from the refrigerator. Leave it in the marinade made with ½ cup olive oil, 1½ cups red wine, ¼ cup soy sauce, 2 Tbsp Worcestershire sauce, 2 Tbsp chopped fresh rosemary, 4 smashed garlic cloves, and salt + black pepper to taste while it starts losing the refrigerator chill.
  2. START THE RISOTTO
    Melt 1 Tbsp of the divided butter in an oven-safe pot over medium heat. Add 1 small finely chopped shallot and cook until softened, about 2 minutes. Add 1 minced garlic clove and cook another 30 seconds.
  3. TOAST THE RICE
    Stir in 1 cup Arborio rice and let it cook for about a minute. You're not trying to brown it. Just get every grain coated and warmed up.
  4. CHEAT CODE RISOTTO
    Pour in 2½ cups chicken broth and bring everything to a simmer. Give it one good stir, cover the pot and move it into the 400°F oven for about 20 minutes. No standing there stirring for half the night.
  5. FINISH THE RISOTTO
    Pull the pot from the oven. Stir in the remaining 1 Tbsp butter and ½ cup freshly grated Parmesan until creamy. Season with salt + black pepper to taste. If it looks tighter than you want, loosen it with extra broth for finishing, if needed.
    S&S SAVE
    Risotto looking more like mashed potatoes than creamy risotto? Don't panic. Add warm broth 1–2 Tbsp at a time, stirring after each addition, until it loosens back up.
  6. GET THE ASPARAGUS MOVING
    Toss 1 bunch asparagus with 1 Tbsp olive oil, ½ tsp kosher salt and ¼ tsp black pepper. Spread it on a sheet pan and roast at 400°F until tender with a little color on the tips.
  7. GET THE GRILL HOT
    You want a properly hot grill before the steak goes down. Pull the 1½–2 lb flank steak from the marinade and pat it fairly dry. Wet steak steams. Dry steak gets that crust we're after.
  8. GRILL THE STEAK
    Put the 1½–2 lb flank steak over high heat and leave it alone for roughly 4–6 minutes per side. Start checking with the thermometer. Pull it around 130–135°F for medium-rare.
    YO DUDE!
    See those little beads of juice starting to push up on the top of the steak? That's your cue to start checking the temp. Don't wait for the 4–6 minute clock to make the decision. The thermometer makes the call.
  9. LET IT REST
    Move the steak to the cutting board and leave it alone for about 10 minutes. Yes, it smells amazing. No, that does not mean you should cut into it yet.
Flank steak being sliced against the grain
LEARNING POINT — CUT AGAINST THE GRAIN Look at the steak before you slice it. You'll see long lines running through the meat. That's the grain.

Turn your knife so you're cutting across those lines, not in the same direction. Then slice the steak thin.

Shorter muscle fibers = more tender bites. Same steak. Huge difference.
  1. SLICE + SERVE
    Slice the rested 1½–2 lb flank steak thinly against the grain. Spoon the creamy Parmesan risotto onto the plates, add the asparagus, then lay the steak alongside it. Dinner's ready. Get out of the kitchen.

THE TIMELINE

3:00
Steak into the marinade. Give the flank steak the full four hours in that rosemary red wine marinade. Into the fridge and forget it.
6:30
Steak out. Pull it from the refrigerator. Leave it in the marinade and let it start losing the refrigerator chill.
6:45
Oven on — 400°F. Everything else should already be prepped and ready.
7:00
She's here. Make two Rosemary Bourbon Smashes. Have a drink together before cooking.
7:15
Risotto starts. Shallot, garlic, Arborio rice, broth. Bring it to a simmer, cover it and into the oven.
7:35
Cheat code complete. Pull the risotto. Stir in butter and Parmesan until creamy. Cover it and keep it warm.
7:35
Asparagus in. Olive oil, salt, pepper. Into the 400°F oven.
7:40
Fire up the grill. Get it screaming hot. Pull the steak from the marinade and pat it fairly dry.
7:45
Steak on. Grill roughly 4–6 minutes per side. Use the thermometer. Pull around 130–135°F for medium-rare.
7:57
Steak rests. Ten minutes. Asparagus should finish too.
8:07
Slice + plate. Slice the flank steak thinly against the grain. Risotto down, steak alongside, asparagus.
8:12
Dinner. Done cooking. Go enjoy the night.

★ BONUS POINTS

  • WARM THE PLATES
    Slide the dinner plates into the warm oven for a few minutes after the asparagus comes out. Hot risotto on a cold plate cools down fast. Small move, restaurant-level difference.
  • SLICE THE STEAK AT THE LAST SECOND
    Let the steak rest whole while you're finishing everything else. Don't slice early just because you've got five minutes to kill. Whole steak stays hotter and juicier. Slice when you're ready to plate.
  • PUT THE PHONES AWAY
    Dinner's ready. Phones off the table. You just spent four hours marinating a steak — Instagram can survive without you for an hour.
  • HAVE THE SECOND DRINK DECIDED
    Rosemary Bourbon Smash starts the night. Have a bottle of red wine ready for later and let the night decide where it goes.
  • SAVE A LITTLE RISOTTO INSURANCE
    Before you sit down, keep a splash of warm chicken broth nearby. Risotto can tighten up while you're slicing the steak and getting the plates together. One splash, one stir, and it's creamy again. Nobody needs to know there was a rescue operation.

★ THE FINISH

Stop cooking. Start the date.
  1. Clear the dinner plates. Dinner's on the table and the hard part is over. When you're finished, get the plates out of the way. The kitchen can wait.
  2. Pour the wine. The Rosemary Bourbon Smash started the night. Now open that bottle of red and settle in.
  3. Change the scenery. Couch. Patio. Fireplace. Somewhere that doesn't feel like you're still sitting at dinner.
  4. Put the phone away. You already got the food picture. The rest of the night doesn't need an audience.
  5. YOU'RE DONE PERFORMING. The steak got four hours. The risotto got twenty minutes. She gets the rest of the night.

    Good food leads to amazing nights.
THE S&S PHOTO RULE Looks like the picture?
No? Perfect!
Would Gordon Ramsay yell at it? Probably. Is she going to? Probably not. Honest effort, amazing food, and the night is young.
Rosemary Red Wine Flank Steak
Close enough. Eat it.