Place rack in center of oven and preheat to 350 degrees F. Grease 9" by 5" loaf pan.
Heat rum in microwave until very hot. Place dates in small bowl and pour in rum.
In double boiler, over hot, not boiling, water, melt chocolate with canola oil.
In large bowl use fork to combine flour, sugar, salt, baking powder, and baking soda.
In large bowl of stand mixer using whisk attachment, beat egg, milk, and vanilla just until mixed. Add flour mixture, dates with rum, and melted chocolate. Stir until uniformly combined, scraping down sides of bowl as necessary. Stir in nuts and chocolate chips. Pour into prepared loaf pan.
Bake 1 hour 15 minutes, until a wooden toothpick inserted in center comes out clean. Remove from pan onto cooling rack.