Date Night Line Up: Flank Steak & Crispy Potatoes with Cilantro Tequila Gimlets

1. **Prep Steak:** Let the flank steak sit at room temperature for 30 minutes. Season generously with kosher salt and pepper.
2. **Make Creamy Chimichurri:** Combine 1/2 cup cilantro, 1/4 cup flat leaf parsley, 1 tbsp fresh oregano, 1/2 shallot, 2 cloves garlic, 1 small jalapeño, 1/2 avocado, 2 tbsp red wine vinegar, and 1/2 cup olive oil in a blender or food processor. Blend with an immersion blender until creamy. Season to taste with kosher salt and pepper.
3. **Prep Crispy Potatoes:** Preheat oven to 450 degrees F (230 C). Cut 4 russet potatoes into small cubes. Toss them with 1 tbsp avocado oil, 1/2 tsp paprika, kosher salt, and pepper until evenly coated.
4. **Cook Crispy Potatoes:** Spread the seasoned potatoes in a single layer on a baking sheet. Roast in the preheated oven for about 12 minutes per side, or until golden brown and crispy (approximately 24 minutes total).
5. **Cook Flank Steak:** While the potatoes are roasting, heat some avocado oil in a cast iron skillet over medium heat. Once hot, add the flank steak and cook for about 8 minutes per side for a medium-rare steak. Adjust cooking time for desired doneness.
6. **Make Cilantro Tequila Gimlet:** In a cocktail shaker, combine 2 oz tequila, 1 oz water, 1/2 oz simple syrup, juice from 2 limes, and 1 tbsp fresh cilantro leaves. Add ice and shake all ingredients well until chilled.
7. **Serve:** Pour the Gimlet over fresh ice or into a martini glass. Slice the flank steak against the grain, serve with the creamy chimichurri sauce and crispy roasted potatoes.