I don't love chocolate, so I don't have any tried and true recipes, but I wonder it you could make a fresh pear bundt cake with Poire Williams and do a dark chocolate drizzle or perhaps add dark chocolate chips or both? I've used this recipe and subbed pears in for apples and the Poire Williams in for part of the applesauce. https://www.food.com/recipe/apple-date-bundt-cake-100300

To me pears don't cry out for chocolate....I love both separately but I think pears are best with vanilla.

Not a recipe, but I have recently tried chocolate hummus (I think Annie (?) perhaps suggested it in another thread). It can be found at Trader Joe's and Aldi. It doesn't have a strong chocolate taste, and it's not overly sweet. I like to dip apples in it--obviously, you control the amount with your dip! I bet it would be good with pears.

The problem is that both pears and chocolate can lose their flavors in baking. The only way I've had both together where they were equally prominent is chocolate dipped dried pears.

Just thinking about it, perhaps poached pears with a black mole? The mole is actually mostly mixed fruits, but they support the chocolate note. You can add a little good cocoa powder if you want to make it chocolatyer.

If you want a cake, maybe a pear upside down cake, with dots of chocolate in between the pear slices?

A reduced pear panna cotta with chocolate ganache? I don't know if the pear will come through as well in the panna cotta, though.

Or pear crepes with chocolate ganache?

Chocolate ice cream with chunky pear sauce? Make it like applesauce, but without added water or sugar to concentrate the pear flavor.

Chocolate mousse or chocolate souffle with pear jam?

Pear fritters dusted with rich dark cocoa powder mixed into confectioner's sugar?

Profiteroles filled with pear chunks and chocolate pastry cream.

I'll be interested to hear how your cake comes out. Good luck!

Gotta agree regarding pears and blue cheese.

I love pears but never quite get the exact ripeness for fresh eating but have been successful making delicate chocolate pear jam. I do agree with gardengal about pears with blue cheese, mine with butter on crusty bread and glass of chardonnay, and I'm expecting a couple dozen pears from monthly fruit gift and I am so ready. Not ever tried poached pears in red wine - not a big red wine fan anyway but I do make a moscato poached pear with star anise and hint of ginger that is thrilling to my taste buds - might want to add a drizzle of chocolate next time.

pear and chocolate beignets?

Pear and chocolate tart. Lovely.

Yes, pears, blue cheese and walnuts.

For the pear and blue cheese fans. I've not made this myself but have had the pleasure of eating it. Nice for this time of year, too. As I recall, it was served with mixed greens instead of arugula.

Roasted Pear and Blue Cheese Salad (Serves 6)

3 ripe but firm Anjou pears
Freshly squeezed lemon juice (3 lemons)
3 ounces coarsely crumbled sharp blue cheese
1/4 cup dried cranberries
1/4 cup walnut halves, toasted and chopped
1/2 cup apple cider
3 tablespoons port
1/3 cup light brown sugar, lightly packed
1/4 cup good olive oil
6 ounces baby arugula
Kosher salt

Preheat the oven to 375 degrees.

Peel the pears and slice them lengthwise into halves. With a small, sharp, paring knife and a melon baller, remove the core and seeds from each pear, leaving a round well for the filling. Trim a small slice away from the rounded sides of each pear half so that they will sit in the baking dish without wobbling. Toss the pears with lemon juice to prevent them from turning brown. Arrange them, core side up, in a baking dish large enough to hold the pears snugly.

Gently toss the crumbled blue cheese, dried cranberries, and walnuts together in a small bowl. Divide the mixture among the pears, mounding it on top of the indentation.

In the same small bowl, combine the apple cider, port, and brown sugar, stirring to dissolve the sugar. Pour the mixture over and around the pears. Bake the pears, basting occasionally with the cider mixture, for 30 minutes, or until tender. Set aside until warm or at room temperature.

Just before serving, whisk together the olive oil, 1/4 cup lemon juice, and 1/4 cup of the basting liquid in a large bowl. Add the arugula and toss well. Divide the arugula among 6 plates and top each with a pear half. Drizzle each pear with some of the basting liquid, sprinkle with salt, and serve.

Not a cake, but a favorite dessert of mine is Pears Belle Helene

https://www.thespruceeats.com/french-pear-dessert-poires-belle-helene-1375196

I think a good riff would be a pear cake with a drizzle of chocolate sauce, or a pear strudel or turnover with some chocolate bits added into the filling. Or flip it and do a chocolate cake with a warm pear sauce over it. I love pear cake but rarely make it due to having weight issues in my old age and not many folks to share with so I make almost exclusively pear muffins these days. I don't think I would put chocolate chips in those though, too much of a texture contrast. Maybe the tiny ones . . . I have enough trouble getting the flavor and texture of the pears to jibe in a pear muffin recipe. I could see maybe a pear bundt cake with a chocolate glaze too.

Lots of great ideas here. Thanks, everybody!

I ended up making a different pear cake than I planned. I used a recipe for pear and walnut cake, a basic sour-cream coffee cake I had not tried before, because it had pears in it, while the (better) one I usually make has them only on top. I drizzled small amounts of a chocolate glaze that I had on hand into half the cake. It didn't really make much of an impression! The cake was good, but the topping was way too sugary, as I should have realized from the recipe. Would have been better with the crumb topping I use on apple crisp. So the pear flavor was there, but because it was a thin cake, the topping dominated. The idea of a pear bundt cake is a better one. I think I would serve it with chocolate whipped cream on the side. Love the chocolate Sabayon idea too. Lpink, I came upon Poires Belle Hélène in my searches and couldn't believe I'd forgotten all about it.

Maybe a barely-chocolate cake with pears in it....

I make a date cake with a chocolate chip crumb topping, might be good on a rustic pear cake or pear tart.