Herb-Smothered Flank Steak with Stuffed Eggplant Wedges

 
At my home, grilling doesn’t get more perfect than a medium-rare charred piece of meat and tender, flavorfull roasted veggies.  This meal is a great way to feed a hungry crowd on the cheap (and the quick!)  Remember your flank steak science, though: never cook past medium rare, let the meat rest at least 15 minutes, and always slice on a steep bias. 

Makes: 4 people long for margaritas
Total kitchen time: 1 hr, plus marinating time

Shopping list:

• 1 2-2.5 lb. flank steak
• 1 large eggplant
• 8 cloves garlic, smashed
• 1/4 cup cilantro, coarsely chopped
• 2/3 cup mint, coarsely chopped
• 2 small red or yellow peppers, coarsely chopped
• 1 tsp. cayenne pepper
• 1 tsp. ancho chile powder (or fajita seasoning)
• 1/4 cup coarse breadcrumbs (diced day-old bread is best)
• 1 tbsp. grated lemon zest
• 1/4 cup shredded jack cheese
• olive oil
• coarse salt and freshly ground black pepper

1. Combine half the smashed garlic, half the cilantro, half the mint and all the peppers in a small food processor and pulse until the mixture is pretty fine, but not a paste.  If necessary, add a tbsp. of olive oil to help things out.
2. Liberally salt and pepper both sides of the flank steak, and season with cayenne pepper and chile powder.  Rub with olive oil and 2/3 of the garlic mixture you just made.  Reserve the rest for after the meat has cooked.  Let the meat marinate in the fridge for up to 12 hours.  Let the meat rest at room temperature for 45 minutes before cooking.
3. Preheat your grill on high heat and make sure your grates are nice and clean.
4. Cut off the top and bottom of the eggplant.  Slice the eggplant into 4 wedges, lengthwise.  Then, score the flesh of the eggplant deeply (but not going through) with your knife at 1/4” spacing.  Turn the eggplant 90° and score it again to form a crosshatch.  Toss the eggplant with olive oil until lightly coated, then salt and pepper.
5. In your mini food processor, pulse together the remaining garlic, cilantro, and mint along with the bread crumbs, lemon zest and 1 tsp. of olive oil.  Rub the mixture into the scored flesh of the eggplant, pushing it down into the cracks. 
6. Grill the eggplant, flesh side down, just long enough to develop char marks, about 1 minute per side.  Set the eggplant on a rack above the grilling surface, or on a cooler side of the grill.
7. Grill the flank steak until medium rare, about 6 minutes per side.  Let the meat rest at least 15 minutes before slicing.  Slice the flank steak on a steep bias with a sharp knife.
8. Arrange the sliced meat, eggplant, and whatever other good stuff you’ve got going on a large platter.  Sprinkle the shredded jack cheese over the eggplant and serve to adoring fans.

If you can get comfortable grilling flank steak, you will always have a date for dinner.  Throw in a cool red wine or a pitcher of sangria and it’s a party!