Pear, Caramelized Red Onion, and Cheddar Grilled Cheese + The Hack

Oh November. How I love you. It might be the best month because it’s the beginning of the holiday season while still holding the fall charm of changing leaves and crisp weather.

Cozy vibes at full force before the craziness of December and the monotony of the later months of winter. Perfect for binging on a new show or curling up with a book while something bakes in your kitchen or slowly bubbles away on the stove.

Enter this grilled cheese.

Ever since I was a kid, I’ve associated grilled cheese with slow afternoons in the house. Warming up after romping around outside. In true Midwest fashion, Kraft singles were the cheese of choice on white bread served up with Campbell’s tomato soup. Don’t forget the saltines.

Then, as a teen, my mom and I were out and about shopping after a visit to our town farmer’s market, and I had a fancy grilled cheese. For the first time. I think it had a bunch of melty cheddar cheese with some caramelized onion on two big slices of cinnamon swirly bread.

That might have been the first time I had a ramped-up version of a childhood classic. I never turned back.

This grilled cheese has been made in that vein with the sharpest cheddar I could find, caramelized onion, and softened bits of pear. Plus, I take advantage of a little-known grilled cheese trick (hack, if you will), to get the best possible melty interior with perfectly toasted exterior.

Generally, we use butter on the slices of bread to get a really crisp, browned outside of the sandwich. Mayonnaise is going to change all that in a great way. Mayo has a high fat content, just like butter, but it doesn’t brown as quickly. The milk solids in butter are responsible for the browning, and they brown pretty fast. I’m sure you’ve had a grilled cheese that didn’t get all the way to melt-city on the inside before the outside was close to burning. Here, the sugars and proteins in mayo are lesser and brown less readily. Therefore, it gives you more time to griddle the sandwich and get to gold. Also, that high percentage of fat gets you just as crispy as butter does. Don’t worry, the mayo doesn’t lend a mayonnaise flavor really. Just the benefits in the pan! 😉

For pairing, I wanted to pick something that could stand up to the sharp cheese and slightly vinegar-y onions. I chose a chardonnay because of the full-bodied silky mouthfeel. Check out this post for the science behind that unique chardonnay characteristic. The pear also picks up a lot of those light, fruity notes.

A red would be amazing for this as well, but pick something like a blend or a pinot noir to balance out the acidity of the sandwich.

And before we get the sandwich, here’s a catch up from the fun, frolicking adventures of October! I’m still digging the New England vibes here in Boston. From the blog, remember that epic #virtualpumpkinparty we had here? And this mega-cozy chili with biscuits baked on top? Pssst. Also don’t forget to look at my “This Month” page to get a sneak peek into all I’m looking forward to this month plus what to cook and recipe highlights from the archives.


Pear, Caramelized Red Onion, and Cheddar Grilled Cheese

Makes 1 sandwich, plus plenty of pear/onion mixture

1 tablespoon olive oil

1 small red onion, chopped

1 ripe, firm pear (I used red Anjou), peeled, cored, and roughly chopped

3 tablespoons red wine vinegar

1 teaspoon brown sugar

Salt and pepper

1-1 1/2 ounces mixed sharp white and yellow cheddar cheese, grated

2 slices sourdough bread



  1. In a large skillet, heat the olive oil at medium heat until glistening and hot. Add the onion. Stir occasionally, letting the onion soften, about 5 minutes. Add the red wine vinegar and brown sugar to the pan, mixing to combine. Reduce heat to low and let the liquid evaporate as the onion continues to soften and caramelize.
  2. Once the onions are very soft and beginning to caramelize, about 15 more minutes, add the pear. Stir to combine and season with a pinch each of kosher salt and black pepper. Heat for another 5 minutes to soften the pears. Remove from the heat and let cool.
  3. In another, smaller skillet, heat a small nub of butter over medium heat. Spread mayo on one side of a slice of bread. Place the bread, mayo-side down, in the pan. Arrange the cheese on top followed by a couple scoops of the onion/pear mixture. Spread mayo on one side of the other slice of bread. Place it mayo-side up on top of the assembling sandwich in the pan.
  4. After a couple minutes of heating, the sandwich should be ready to flip. Carefully flip the sandwich over. Heat for another couple minutes to brown the other side.
  5. Remove to a plate and eat immediately



    • Kelsey
      November 1

      Thanks Sara! xoxo

  1. November 8

    I’ve never made grilled cheese with pear before, so I must say I’m really curious to try it. Bet it’s delicious!!

    • Kelsey
      November 9

      Thanks Diego! Very delicious–highly recommend :)

  2. November 8

    OMG, I get it now when girls can’t even. I can’t even wait to make this sandwich! I love putting pear into meals. I sneak it in whenever I can, however, I’ve never put it in a grilled cheese. I can’t wait to make this sandwich!

    • Kelsey
      November 9

      Yes! You’ll love it! xoxo

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