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Grilled Short Ribs and Lettuces with Mustard-Orange Dressing

['1 tsp. crushed red pepper flakes (optional)', '1/2 cup plus 1 tsp. orange marmalade', '2 Tbsp. plus 2 tsp. whole grain mustard, divided', '3 Tbsp. white wine vinegar, divided', '1 tsp. freshly ground black pepper, divided, plus more', '3 lb. (1/4"–1/2"-thick) crosscut bone-in beef short ribs (flanken style)', '3 1/2 tsp. kosher salt, divided, plus more', '2 garlic cloves, finely grated', '1/4 cup plus 2 Tbsp. extra-virgin olive oil, plus more for grill and drizzling', '2 romaine hearts, halved lengthwise', '1 head of radicchio, quartered through core', 'Crusty bread (for serving; optional)']

Stir red pepper flakes (if using), 1/2 cup marmalade, 2 Tbsp. mustard, 1 Tbsp. vinegar, and 1/2 tsp. black pepper in a small bowl.
Place ribs in a glass baking dish; season all over with 2 tsp. salt. Pour marinade over and turn ribs to coat. Let sit at room temperature at least 15 minutes and up to 1 hour.
Whisk garlic, 1/4 cup plus 2 Tbsp. oil, 1/2 tsp. salt, 1/2 tsp. pepper, and remaining 1 tsp. marmalade, 2 tsp. mustard, and 2 Tbsp. vinegar in a small bowl or measuring cup.
Prepare a grill for high heat; oil grate. Grill ribs until lightly charred and crisp around the edges, about 2 minutes per side. Transfer to a platter, season with salt, and let rest 5 minutes.
Drizzle cut sides of romaine and radicchio with oil, then season with 1 tsp. salt. Grill, turning occasionally, until lightly charred and warmed through, about 2 minutes for the romaine and 5 minutes for the radicchio. If using bread, grill alongside radicchio until lightly charred and warmed through, about 2 minutes per side. Transfer to platter with ribs.
Pour dressing over charred lettuces and ribs; season with more salt and pepper.
Do Ahead: Marinade and dressing can be made 1 day ahead. Cover and chill. Ribs can be marinated 8 hours ahead. Cover and chill then let sit at room temperature at least 15 minutes and up to 1 hour before grilling.

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