January 16, 2023 Jump to recipe

endive salad with caramelized grapefruit dressing

a salad to get us through the winter

By all accounts, a salad made almost entirely of bitter, astringent ingredients has no business tasting as good as this one. And yet this is not some “healthy” thing masquerading as a wildly out of character aspirational item, like when kelp tries and fails to be noodles (sorry, Big Kelp). This salad tastes emphatically like what it’s made from, but with the more challenging flavours balanced by jewels of pomegranete, orange, and the wonder that is caramelized grapefruit.  Not to be dramatic (the universal sign that someone is about to be really dramatic), but this salad makes me feel like I’ll make it through the winter. 

It’s the bright, energetic crispness of it all; the sweetness of the fruit, the red and orange and green you’re not apt to see in the natural world till well after the first thaw. To maximize contrast, I like to make this on the meanest of winter days—the kind where blowing snow and greying slush makes you wonder why anyone ever thought to settle in the frigid hellscape that is Canada in January. Plus, it’s made of ingredients generally available in the colder months (and not available-but-sad, like languid grocery store peaches and people on Tinder after bad breakups). 


The secret is caramelized grapefruit in the dressing, which for the uninitiated, is just a cut grapefruit coated in sugar and browned in a pan. Bitter endive and radicchio need sweetness to balance them out, and caramelized grapefruit juice is vastly more interesting than a bit of straight sugar in a vinaigrette. That said, Mary Poppins was right—a spoonful of sugar really does help the proverbial medicine go down, whether that’s tidying your room or attempting to take the edge off bitter greens.

While this works particularly well on the side of fish and rice, I’ve eaten a massive bowl on its own numerous times and felt much better for it. Salad may not be the obvious option when you have to put on seventeen layers and spiritually steel yourself for a walk to the mailbox, but if you’re looking for a vibrant interlude between an endless parade of winter stews, this might be it. 

endive salad with caramelized grapefruit dressing


Belgian endive 3 heads
radicchio half a small head
fennel 1 small head
mint 1 cup, loosely packed
pomegranate seeds 1 cup
grapefruit 1 large
orange 1 large


grapefruit 1/2 a large
kosher salt 1/4 teaspoon
white balsamic vinegar (or regular balsamic) 1 tablespoon
honey 1 tablespoon
dijon mustard 1/2 teaspoon
extra virgin olive oil 1/4 cup
granulated sugar a few tablespoons (enough to coat a cut edge of grapefruit)

make the dressing

Sprinkle a few tablespoons of granulated sugar on a small plate. Cut the grapefruit in half through its equator and dip it in the sugar to coat. Brown in a small, nonstick pan preheated on medium till it’s bubbly and caramelized, about five minutes.

Juice the grapefruit half into a bowl, using a small strainer to catch any seeds (or just fish them out after). Add the salt, dijon, honey, and white balsamic vinegar, and whisk to combine.

Slowly drizzle in the olive oil while whisking to emulsify. It may not emulsify completely, and that’s just fine.

seed the pomegranate

Honestly, I like to buy seeded pomegranate because I think the extra cost is worth my sanity, but if you’re working a whole pomegranate, here’s the cleanest way to de-seed it.

Cut around the crown with a paring knife and remove it like a hat. Make superficial cuts from top to bottom around the entire the perimeter (space the cuts about an inch apart). Pull it apart and dunk the whole thing in a bowl of water. Rubbing the seeds out underwater not only means the seeds sink while the flesh floats, but protects you from impossible-to-remove stains.

make the salad

Chop the endive into bite-sized pieces by cutting horizontally from the side opposite the stem. You’ll get a few larger chunks of the core—chop those into quarters. Thinly slice the light part of the fennel, reserving the fronds for garnish. Cut the radicchio in half, cut out the core, and shred it.

Roughly chop the mint.

Depending on your tolerance for this sort of thing, either supreme your grapefruit and orange (cut the fleshy part out of the pith) or simply peel them into segments. I’d recommend the former for at least the grapefruit, since the bitter, white pith might overwhelm this salad. Here’s how to do that.

Put it all together in a big bowl.


Toss it all together—unless you’re planning on serving some later, in which case you’ll want to store the salad and dressing separately. Garnish with fennel fronds and enjoy absorbing its various good-for-mes. Warmer days are coming, they say.


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