Grilled Ham and Cheese Sandwich with Jammy Bourbon Cherries

2 slices sourdough bread, buttered
2 slices Swiss cheese
4 slices deli ham

For the jammy bourbon cherries:
1 cup frozen cherries
1/2 cup white sugar
pinch cinnamon
1 teaspoon freshly cracked black pepper
1 tablespoon salted butter
1 tablespoon lemon juice
2 tablespoons bourbon (optional)

Instructions

1. Make the jammy bourbon cherries: combine the frozen cherries, sugar, a pinch of cinnamon and the cracked black pepper in a small saucepan set over medium heat. Stir occasionally as the cherries thaw and release their juices. After about 5 minutes, use a spoon to gently break up larger cherries so the mixture becomes saucy.
2. Lower the heat to a gentle simmer and cook another 10–15 minutes, stirring now and then, until the cherries have reduced and the mixture is thick and glossy. Remove from the heat and stir in the butter, bourbon (if using) and lemon juice. Let the jam cool slightly so it thickens further—this helps prevent the sandwich from becoming soggy.
3. Heat a skillet or griddle over medium heat. Place one slice of buttered sourdough on the pan, butter-side down. Spoon a generous layer of the jammy bourbon cherries onto the bread, then top with the Swiss cheese. Fold the ham slices and layer them on top of the cheese. Finish with the second slice of sourdough, butter-side up.
4. Cook until the bottom is golden brown and crisp, about 4–6 minutes. Carefully flip the sandwich and continue cooking until the second side is browned and the cheese has melted, another 3–4 minutes. Adjust the heat as needed to avoid burning while allowing the cheese to fully melt.
5. Transfer to a cutting board, let rest for a minute, then slice and serve immediately. The contrast between the savory ham and Swiss and the sweet, slightly boozy cherries is best enjoyed warm.