The Ultimate Hawaiian Grilled Cheese

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Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-BasilI think it’s important to do things for people just because you love them, especially in a relationship.

Luckily, my roommate also subscribes to this philosophy, and he does all kinds of randomly nice things for me. He laughs at all my jokes, gives me the comfy side of the couch, runs my baths, and always remembers to buy the good toothpaste. He doesn’t make me drive on road trips, and he never complains when I have an inconvenient panic attack, put my retainer on the table, eat all the Sour Patch Kids at the movies, or talk about how I want Taylor Kitsch to move in with us. He compliments my outfits. He eats kale. He lets me write The Dude Diet.

You get the point.

I very much appreciate these thoughtful things, and I do my best to show Logan affection in similarly selfless ways. For example, I noodle with him at Widespread Panic concerts, accompany him to barbecue festivals and sporting events, and take naps on the couch when he watches football or worse, golf, because he wants to “be together.”

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-2I also don’t make him wear a sleep apnea mask for his snoring (even though I’m pretty sure he needs one), and whenever I buy ice cream on Sundays, I let him gold dig all the good stuff. I fetch him Zantac when he’s incapacitated himself after a feast, wrestle with our miniature mailbox everyday, and entertain the idea of maybe getting a dog together (in like ten years).

And sometimes when I’m feeling particularly loving, I throw Dude Diet caution to the wind and surprise Logan with something unexpected and incredibly dank for dinner in the middle of the week. Like The Ultimate Hawaiian Grilled Cheese…


Basically, this is the world’s fanciest Hawaiian pizza in grilled cheese form, which is genius. Grilled cheese=increased crunchy surface area, more cheese, and less doughy distraction from the glorious flavors of prosciutto and grilled pineapple.

Yes, grilled pineapple. Grilling the pineapple is key here, people. I know it may seem like a frivolous extra step, but it’s non-negotiable. A few short minutes on the grill (relax, you can just use a regular pan in a pinch) softens and lightly caramelizes the fruit, while adding a subtle smoky flavor that will blow your mind, rock your world, change your life, etc. The sweetness of the grilled pineapple is the perfect complement to the salty prosciutto di Parma, and sandwiched between two slices of fresh multigrain bread with lots of ooey-gooey melted mozzarella and fresh basil? Sweet and savory gold mine. It’s almost too epic to bear.

Then you dunk the whole thing in spicy tomato sauce and the world explodes.


After taking my first bite, I was overcome by an urge to spike the prop pineapple (seen in the background of these photos) on my living room floor while doing one of the Victor Cruz-esque salsa moves I learned in Zumba last week. Thankfully, I have superhuman restraint, and I settled for my standard creepy silent cheer and envisioning my roommate losing his shit when he got a load of this bad boy.

And lose his shit he did.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-50There were no tears, which is obviously my ultimate goal when cooking for Logan, but he was visibly moved by the beauty of this heavenly sandwich and my love for him (definitely in that order). He actually stopped eating mid-sandwich, and when I asked what was wrong, he somberly replied that he was just “really, really sad that it was already halfway gone.” Deep thoughts by the Dude.

After finishing his Hawaiian grilled cheese, stretching, and making sure I wasn’t hiding a second sandwich anywhere, he shook my hand and congratulated me on a job incredibly well done. This was a new move, but I think I prefer the handshake to the high five. It has more gravitas, which seemed appropriate for such a feat of culinary wizardry.

Get after it, friends. Spread the love…

The Ultimate Hawaiian Grilled Cheese: (Makes 2 Chronic Sandwiches)

½ pineapple, peeled, cored and cut into ½ inch planks
Kosher salt
4 slices multigrain bread
2 tablespoons softened butter
1½ cups shredded part-skim mozzarella cheese
1/3 pound thinly sliced prosciutto di Parma
¼ cup fresh basil, chopped
Marinara or arrabiata sauce for dipping

Preparing your Ultimate Hawaiian Grilled Cheese:

-Start with the pineapple. Peel and core the pineapple (you can usually find peeled, cored pineapple at the market to make things easier), and cut ½ of the pineapple into planks about ½ inch thick. Season each plank with a little kosher salt.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-1-Heat a grill or grill pan over medium-high heat. When hot, add the pineapple and cook for about 3 minutes on each side until sexy grill marks appear and the fruit is lightly caramelized. Briefly set aside.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-2-Now it’s time to assemble the grilled cheese. To assemble each sandwich: Butter one side of each piece of bread with ½ tablespoon softened butter.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-3-Place the bread butter-side down on a cutting board and top one piece of bread with about ¼ cup cheese.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-4-Add a layer of prosciutto.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-5-Sprinkle prosciutto with about 2 tablespoons of cheese, and then add half of the grilled pineapple and half of the chopped basil. (I forgot to put the basil in this photo. I know some of you freak out without the visual, so I apologize.) Sprinkle with another 2 tablespoons of cheese.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-6-Go ahead and put another layer of prosciutto on that bad boy and top it with the remaining ¼ cup cheese.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-7-Top with the second piece of bread with the buttered side facing out (duh).

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-8-Heat a large non-stick pan or skillet over medium heat. When hot, add the sandwiches and cover with a lid. Cook for about 4 minutes until the underside is golden brown. Flip the sandwiches and chook for 3-4 minutes more.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-step-9-Remove your epic grilled cheese from the pan and serve immediately with tomato sauce for dipping.

Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-6ALOHA. Don’t forget to dip…


Hawaiian-Grilled-Cheese-With-Grilled-Pineapple-Prosciutto-and-Basil-8Just say YES.

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