I love Lowe's Toronto Christmas Market. It's always a great time, lots of things to do and see. Surely brings out the Christmas Spirit and mood in anyone. It's a terrific place to have a date, share some food and try sample after sample of booze near the Beer Garden. Nice spots with heat lamps and bonfires around to keep your nose warm in the freezing weather, but the small stores are cozy as well.
Mill Street is a great choice for lunch or dinner. The perfect spot for any beer lover as well. Soma is the ideal for chocolate lovers but also gelato lovers (blueberry basil is killer). All the small booths and year-round shops make the market interesting, which can last up to 2 hours or more if done thoroughly.
Make sure to bundle up and also make sure to get free warm beverages everywhere you go!