Add bacon to a large skillet and heat over medium high heat.
Cook for 5-7 minutes until the fat has rendered and the bacon is crisp. Remove with a slotted spoon to a paper towel lined plate and reserve.
Add the remaining tablespoon of olive oil to the skillet, and when the oil shimmers, add the Brussels sprouts cut side down along with a large pinch of salt and cracked pepper.
Cook until charred around the edges, about 5-8 minutes. Stir, and continue cooking another 8-10 minutes until soft, tasting for salt and adding as needed.
Reduce heat to medium and add the pomegranate seeds, vinegar, and red pepper flakes (if using).
Cook for another 1-2 minutes.
Remove from heat and toss the Brussels sprouts with the reserved bacon bits.