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Third-Date Flank Steak

Updated: Nov 5, 2018

A rolled flank steak that will impress your date. With plenty of leftovers for two ... for the next morning. Or, um, you know, whenever.


Flank steak is a cheap cut of yummy beef, perfect for stuffing and spicing up. This is far less difficult than it looks. It just takes a few extra steps and some twine tying.


“This is the best meal I've had since ... ever.” - actual third date quote

Ingredients:

2 lb. flank steak

6 oz. prosciutto

6 slices havarti cheese (Swiss or provolone work, too)

Handful of fresh chopped basil

1/4 cup each chopped red and yellow peppers

1 teaspoon salt

1 teaspoon pepper

1 tablespoon thyme


Preparation:

Preheat oven to 350. On a cutting board, under strong plastic wrap, hammer the steak as flat as you can with a meat mallet. Discard the plastic wrap. Salt and pepper the meat. Layer the ingredients on top of the meat: cheese slices, prosciutto, peppers, sprinkle basil on top.


Starting from a short end, tightly roll up the steak, tucking in all the loose ingredients and edges. Tie the "loaf" with twine every few inches (especially the ends) to hold it together. Cover the "loaf" in thyme.


Cook & Serve:

Roast in 350 oven for 20 to 30 minutes, or until meat thermometer registers 125° for medium rare. Transfer the flank steak to your cutting board, cover loosely with foil and let it sit for 10 minutes. Cut the strings off and cut the steak in about a half-inch slices. Wonderful on its own, but if you wish, serve with a chimichurri sauce. (Aw crap, I should post a recipe for chimichurri sauce.)



A Little Backstory:

I panicked a little, preparing for my third date with Brad. I had invited him to my place for dinner for the first time, and I wanted it to go well. But what in the world would I cook? My wise friend Sarah counseled me to "cook something with beef you've made in the last year and posted on Instagram -- then down a full glass of wine before he gets there." This impressive-looking stuffed steak was the meal showpiece, which I served with roasted potatoes and grilled broccolini. And as Brad said after we cleared the dishes, "That's the best meal I've had since .... ever." Third-date magic, my friends.

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