Gourmet Grilled Cheese with Dates & Olive Oil–Confit Garlic

Written by: Cooks of Heraclea

Time: 1 hour 10 minutes

Ingredients: 9

Gourmet grilled cheese with dates and olive oil confit garlic, sliced to show melted white cheddar on golden sourdough

We took the grilled cheese seriously. A whole head of garlic goes into the oven with our Mature Harvest olive oil until every clove turns soft and sweet — that's the spread. Sharp white cheddar melts over it, Medjool dates bring the sticky-sweet counterpoint, and fresh basil cuts through. Brush the outside with the garlicky confit oil before it hits the buttered skillet. Cook it slow until the bread goes deeply golden and the cheese gives way. Slice, pull it apart, and don't share unless you have to.

Ingredients:

Olive Oil–Confit Garlic

1 whole head of garlic
30 ml Heraclea Mature Harvest Extra Virgin Olive Oil
1 teaspoon kosher salt

Grilled Cheese

4 large Medjool dates, pitted
4 slices sourdough-style bread
90 g sharp white cheddar, sliced (45 g per sandwich)
8 g fresh basil, chiffonaded (4 g per sandwich)
1 teaspoon olive oil from the garlic confit, for brushing
½ tablespoon butter, for cooking

Steps:

Make the Garlic Confit

Preheat the oven to 350°F (175°C) and position a rack in the center.
Slice off the top ¼–½ inch of the garlic head and place it cut-side up on a sheet of aluminum foil set in an oven-safe dish. Sprinkle with salt, then pour the olive oil over the garlic. Bring the foil up around the garlic and seal tightly.
Roast until the garlic is very soft, 45–50 minutes.
Remove from the oven and let cool until easy to handle. Squeeze the softened garlic cloves into a heatproof jar, discarding the skins. Strain the olive oil over the garlic cloves. Use immediately or refrigerate for up to 2 weeks.

Assemble & Cook the Grilled Cheese

Lay the bread slices on a work surface. Spread a few cloves of confit garlic evenly over one side of each slice, gently pressing them into the bread.
Layer the cheddar evenly over two slices of bread.
Open the dates with your hands, remove any remaining pits, and place them over the cheese. Sprinkle with the basil, then close the sandwiches with the remaining bread slices, garlic-side in.
Brush the outside of each sandwich lightly with the olive oil from the garlic confit.
Heat a cast-iron skillet over medium heat and add the butter. Cook the sandwiches, flipping once and adjusting the heat as needed, until the bread is deeply golden and the cheese is fully melted, 6–8 minutes total.
Transfer to a cutting board, slice in half, and serve warm.