Bar Babylon is at Church and Wellesley. By far the best place for a first date. Amazing music (house and down tempo), roaring fireplace, great food, superb service and martini's galore. They infuse the vodka onsite and have about 100 different martini's on the menu. $8.50 for a three ounce martini.
Cobalt at College and Bathurst is a great little place I just discovered. Martini's are pretty good, nice retro vintage feel to the place. Friendly staff but they seem a little disorganzied. Martini's run about $6.50 but on Tuesday they have half priced cosmo's and Hong Kong (lychee liquor, vodka, cran) martini's which can get dangerous really fast. Decent music (80's, alternative rock).
Insomnia at Bloor and Bathurst is another great date place. Live DJ's nightly, good staff, great food and a good range of martini's ($7.50-$12.50 a martini). Martini's are not as good as Bar Babylon.
I like a martini
Two at the most
Three I am under the table
Four I am under the host
~Dorothy Parker
Jillian