second date ideas needed
Where did you end up on your first date? And avoiding the super-core (TIFF will not be your friend):
Negroni/Carpano. Low key. Quiet, not stuffy. Good for talking. I haven't eaten here since they changed to Carpano.
Enoteca Sociale. Boisterous, but not loud. Sit at the bar. Have some wine from the Enomatic machine. Great food.
Globe Bistro is good too, on her end of the city.
Gabardine? Food is okay, space is comfortable and nice.
1288 Dundas St W, Toronto, ON M6J, CA
Although I really like Earls for after-work drinks, I wouldn't be so happy to go there for a date. The waitresses tend to be hired for their looks... not a male server in sight, and it can get pretty crowded Friday after work.
For something more relaxed (i.e. not fine dining) in the general downtown area I'd suggest Rodneys by Bay, The Beer Bistro, or La Bettola di Terroni (sit up at the bar)
18 King St. E, Toronto, ON M5C 1C4, CA