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This BBQ chicken and pineapple grilled cheese came about during one of those Saturday afternoons when I was trying to use up leftover chicken but my kids were whining about "boring leftovers again." My youngest had been obsessing over Hawaiian pizza lately, so when she suggested putting pineapple on a grilled cheese sandwich, I figured why not give it a shot. The combination sounded totally weird at first, but after some trial and error with getting the ratios right, we ended up with this incredible sandwich that's become our weekend go-to. Now every time I cook chicken during the week, someone asks if we'll have enough left over for these sandwiches.
My friend Jenny's fifteen-year-old son tried one of these when he was over gaming with my kids and immediately declared it "actually fire." Coming from a teenager who usually lives on Hot Pockets and energy drinks, that was basically a five-star review. Now Jenny makes them every Sunday because it's literally the only homemade food he'll eat without complaining.
Getting the Ingredients Right
- Thick bread is crucial: Thin bread gets soggy and falls apart with all that filling, while thick sourdough holds up perfectly
- Sharp cheddar works best: Mild cheese just disappears with all the other flavors going on
- Good BBQ sauce matters: Since it's coating everything, cheap sauce makes the whole sandwich taste off
- Fresh pineapple if possible: Canned works fine but fresh has better texture and doesn't add weird syrup
- Quality chicken counts: Leftover rotisserie or properly cooked chicken beats processed lunch meat every time
- Real butter for the outside: Makes that golden crust that's the whole point of grilled cheese
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Making Them Step by Step
- Getting the chicken ready
- Heat your oven to 350 and put the chicken breasts in a baking dish. Slather them with about half the BBQ sauce and bake for twenty minutes until they're cooked through. Let them cool enough to handle, then shred with two forks and mix with the rest of the sauce.
- Setting up for assembly
- Butter one side of each bread slice and lay them all out butter-side down. This sounds obvious but it makes assembly way faster when you're not fumbling around trying to figure out which side is which.
- Building the layers
- Put about a quarter cup of cheese on four of the bread slices. Add the saucy chicken mixture, spreading it out evenly. Layer on three thin pineapple slices per sandwich, then top with more cheese. The cheese on top and bottom helps everything stick together.
- Finishing the sandwiches
- Put the remaining bread slices on top, butter-side up, and press down gently so everything holds together. Don't smash them flat, just compress slightly so they don't fall apart when you flip them.
- Grilling them properly
- Heat a large skillet over medium heat and spray with cooking spray. Cook two sandwiches at a time, about three to four minutes on the first side until golden brown. Flip carefully and cook one to two minutes more - the second side goes way faster so watch it closely.
- Serving them right
- Cut each sandwich in half diagonally and serve immediately while the cheese is still stretchy and the bread is crispy. Don't let them sit around or they get soggy.
I totally messed up my first batch because I cranked the heat too high and ended up with burnt bread and cold cheese in the middle. I also tried to cram too much chicken in because I thought more was better, but they just exploded when I flipped them. Once I figured out the right heat and proportions, these became basically foolproof.
How to Serve Them
These are best right off the skillet while everything's hot and gooey. I usually serve them with chips and pickles because that's what everyone expects with a grilled cheese. Sometimes I'll make a simple salad to feel better about all the cheese and butter, but honestly they're filling enough on their own.
Switching It Up
You can use different BBQ sauces depending on what your family likes - honey mustard BBQ is really good, or spicy if you want some heat. Sometimes I add thin apple slices instead of pineapple for a different kind of sweetness. Turkey works too if you have leftover Thanksgiving bird hanging around.
Leftovers and Storage
These don't really keep well because the bread gets soggy, but the chicken mixture lasts in the fridge for a few days and makes great quesadilla filling. If you absolutely must reheat one, use a toaster oven rather than the microwave to try to get some crispness back.
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These BBQ chicken and pineapple grilled cheese sandwiches have become our Saturday tradition when we want something that feels indulgent but doesn't require leaving the house or spending a fortune. They hit that perfect comfort food spot where familiar flavors get combined in a way that feels new and exciting. My kids specifically request these now when they want "good food" for lunch, which is saying something since they usually just want chicken nuggets for everything.
Frequently Asked Questions
- → Can I use leftover chicken instead?
- Yes! Use about 2 cups of cooked, shredded chicken. Just mix it with BBQ sauce and you're ready to go.
- → What type of pineapple works best?
- Fresh pineapple rings are ideal, but canned works too. Just make sure to drain canned pineapple well so it doesn't make the sandwich soggy.
- → Can I use different cheese?
- Sharp cheddar works great, but you could try monterey jack, gouda, or even pepper jack for some heat. Just pick something that melts well.
- → How do I prevent the sandwich from falling apart?
- Don't overfill and press gently when assembling. Cook on medium heat so the cheese has time to melt and act as glue before the bread burns.
- → Can I make this without an oven?
- Sure! You can use a slow cooker, poach the chicken, or even use rotisserie chicken from the store. Just shred it and mix with BBQ sauce.
- → What should I serve with this?
- These rich sandwiches pair well with simple sides like coleslaw, potato chips, or a light salad to balance the richness.