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Layer up the brioche, pears and chocolate, and make the custard, a few hours before cooking. Keep covered in the fridge.
Cut the brioche into 14 slices, then butter a large baking dish, about 20 x 28cm base measurements. You’ll also need a roasting tin large enough to hold the dish.
Slice each pear half into 3 or 4 wedges and pat dry on kitchen paper. Arrange the brioche in the baking dish, tucking in the pears and scattering in most of the chocolate chips as you go.
To make the custard, simply whisk the ingredients together in a large bowl or measuring jug. Pour the custard all over the brioche in the dish and gently press the exposed bread crusts down into the liquid to soak, although some of the brioche will stick up above the level of the custard mixture. Scatter on the rest of the chocolate chips and leave to stand for about 30 minutes to soak up the custard. While the pudding is standing, preheat the oven to 180°C, fan 160°C, gas 4, and boil the kettle.
Sit the dish inside the roasting tin and add boiling water to come about halfway up the outside of the dish (you can cook the pudding without the water bath, but this method ensures a lovely velvety texture).
Bake in the oven for 35-40 minutes until set, golden on top and puffed up. The pudding will shrink back down a little as it cools. Serve warm with cream.