Ham and Pineapple Grilled Cheese Sandwich

This Ham and Pineapple Grilled Cheese Sandwich is the perfect mix of melty, buttery, sweet, and savory in every bite. The salty ham, juicy pineapple, and gooey cheese come together in a way that feels a little fun but still totally comforting. It’s the kind of easy lunch or quick dinner that can make a hard day feel a little more special.

I don’t know how many times I’m going to need to shout it from the roof tops that a Grilled Cheese Sandwich is one of my favorite comfort foods of all time. It is one of the first foods that I ever learned how to make, and grilled cheese sandwiches and ramen basically carried me through high school and secondary education.

The other day I was craving a Grilled Cheese, but I had leftover ham in the fridge from Easter, and inspiration struck and I decided to try to make a Ham and Pineapple Grilled Cheese Sandwich. You guys, it’s so good that I forgot to take a picture of my results until I was already almost half way through it, and I knew instantly that I had to share it (you can see my clever posing to hide the eaten part in the picture above).

Make this Ham and Pineapple Grilled Cheese Sandwich recipe when…

• You want to try something different
• You are craving something comforting, easy, but fun
• You want something cheesy, toasty, and yummy

Ingredient notes…

Here is what you’ll need to make this Ham and Pineapple Grilled Cheese Sandwich recipe. Please be sure to check the recipe card for the exact ingredients and measurements.

• Bread: I used Sourdough bread because it’s sturdier and can handle more toppings. But of course you can use whatever type of bread you prefer.
• Cheese: I think individual sliced cheese is the best for Grilled Cheese Sandwiches when you are trying to put more toppings on it than just cheese. They are sliced thin enough that you still have room for more toppings. I used slices of Havarti but you could always use something like Mozzarella that will still get super melty and stick to the ham. But use whatever cheese you prefer.
• Butter: I use good old salted butter. I like to put it in the microwave for about 8 seconds or so to soften it up and make it easier to spread. There is nothing more frustrating on this earth than trying to spread cold butter and having it rip your bread to shreds.
• Ham: I used leftover ham I had in the fridge but you can use any type of ham such as cold cuts.
• Pineapple: I used sliced pineapple chunks because I had some leftover that I cooked alongside the ham, but if I had pineapple rings I would probably use a pineapple ring as it wouldn’t be as messy as loose pineapple.
• Honey mustard: I decided to put honey mustard on the inside of the bread because I was worried the sandwich might be too dry without it. It was such a good decision. It added the perfect flavor. If you don’t like honey mustard you could always use something else like yellow mustard, Dijon mustard, or even mayo.
• Red onion: I still felt like the sandwich needed something else so I added a few slices of red onion. I found it really tied all the other ingredients in the sandwich together, but you can always omit it if you wish.

Equipment I swear by…

• A good non-stick Skillet

While the Grilled Cheese Sandwich cooks…

This is a quick recipe so you don’t have a lot of hands off time, but you could still make time to:

• take a few slow deep breaths before flipping your sandwich
• open the blinds and let sunshine if it’s sunny out
• tidy a few things in the kitchen so your space feels calmer

How to make it…

See the recipe card below for ingredient quantities and full instructions.

1. Grab your ingredients and spread your honey mustard on one side of each of the slices of bread. Add your cheese to one side of the sandwich on top of the honey mustard. Top with ham, pineapple, red onion, and more cheese and top with the other slice of bread so the honey mustard is on the inside.
2. Butter the top slice of bread and place in a non-stick pan over medium low to medium heat with the butter side facing down. (I find with sourdough I cook on medium and it’s fine, with white bread I usually cook one less than medium)
3. Let cook for about 5-7 minutes if using sourdough bread, and about 3-5 minutes if using something less sturdy like white bread.
4. While the first side is cooking, carefully butter the top slice of bread.
5. Once the bottom is golden brown and the top side is buttered, flip over and cook the other side until golden brown, about another 3-5 minutes.
6. Adjust heat if needed.
7. Remove from pan, cut and enjoy.

My tips and tricks to make this Grilled Cheese Sandwich recipe…

To make it as perfect as possible: Use softened butter. Put it together outside of the pan to keep from spilling ingredients in the pan, getting distracted and flustered like I do. Keep a close eye on your sandwich as it cooks. Check the bottom several times throughout cooking to make sure you don’t overcook it, it reaches your perfect color of golden brown, and make sure the cheese is melting. If the bread is cooking faster than the cheese is melting, you may have put too much cheese inside, or your pan could be too hot. The first time I used Sourdough for my grilled cheese I was shocked at how much longer it took to cook than white sandwich bread, so be patient.

Heartier: Either cut your ham thicker for the sandwich, or double up if using lunch meat. Add more pineapple too if you want.

Spice it up: Try adding some hot sauce to the inside of the bread instead of the honey mustard before you add the cheese to give it a little kick.

For pizza vibes: For more of a ham and pineapple pizza type of vibe, I would substitute pizza sauce for the honey mustard and top with Italian Seasoning.

Storage notes:

While I love hacks and saving time, it’s best to make a Grilled Cheese Sandwich fresh, and it doesn’t take much time at all. I have no shame to admit that I have saved like half a sandwich in the fridge before and warmed it up by putting it in the air fryer for a minute or two. But it didn’t taste as good as it did when I first made it.

If you were in a hurry and making lots of grilled cheese sandwiches at once for a get together or something, you could always assemble them, and even add the butter to the top slice of bread and store in the fridge until you were ready to cook them.

Are you struggling right now…

• If you are running low on energy, motivation, or time, I would just stick with my Classic Grilled Cheese Sandwich instead of worrying about adding the other ingredients. It will still be just as delicious, and with less time and effort.

Thank your for stopping by Comfort In a Bowl. If you create this recipe or any other from our site, we would greatly appreciate you taking the time to share, comment and rate the recipe! Take care of yourself.

What to serve with Ham and Pineapple Grilled Cheese Sandwich

• Crockpot Potato Soup
• Easy Mushroom Soup
• Crockpot Bacon Cheeseburger Soup
• Easy Chicken Tortellini Soup

My burnout situation…

Since it’s nicer out now and I’m trying to develop some healthier habits, I’ve been trying to get my steps lately by going for longer walks outside. Today I decided to take my two small elderly dogs with me (which I also did yesterday). Let’s just say it didn’t go as I’d hoped.

They did well yesterday, I usually just take them on shorter walks around the block, but we have a fairly huge fenced in backyard so they get as much exercise as they want out there. So I decided to take them again and see how they do.

The ground is still kind of wet around where we live. We have little lakes and things in our neighborhood and they still have ice on them. I went walking to where I usually do when I am going for a long walk and there was a guy out there also walking. I thought I heard him swearing farther away, or like talking to himself. So I kind of just kept my distance from him and stayed on high-alert when he came my way. However, I quickly realized why he was swearing when I tried to go around a wet part of the ground and found myself getting stuck in mud. My shoes and socks got soaked and muddy. The dogs paws were covered in mud. I almost lost my shoes but didn’t.

And once we turned around and started to head home my oldest girl started slowing down, and I ended up having to carry this wet dirty dog home for most of it.

So that meant as soon as we got home I needed to get them into the bath. And then there was mud and dog hair all over so I needed to clean my bathroom.

And at first I started feeling sorry for myself: See this is why I don’t try so hard, Look what this does it just created even more work for myself.

But I can tell I am becoming mentally stronger because I let myself be frustrated for a second and then went, nope I still got tons of steps in today. My dogs still got exercise. Now my tub is nice and extra clean for when I want to take a bath later, and tomorrow is a new day.

Conclusion…

It can be easy when things don’t go as planned to want to throw the whole day away. But I love the thought process of if you had $100 and you dropped $1 would you throw the other $99 away? No. So stop letting yourself throw away all your progress simply because things don’t go as planned.

You’ve got this.

Take care of yourself.

-Caitlin