I figure Bloor West Village is roughly half way between those two points. For upscalish, I've heard good things about Bloom near Bloor & Durie. For more casual, there's Dr Generosity and the Yellow Griffin (although both get mixed reviews on this board).
Further west on the Kingsway, there's Merlot and ViBo to consider. I haven't been to either but perhaps someone could comment on their appropriateness.
If you click on any of the place links, you'll see related threads with comments that may give you a better idea of what they're like.
2197 Bloor St W, Toronto, ON M6S1N2, CA
2202 Bloor St W, Toronto, ON M6P, CA
2315 Bloor St W, Toronto, ON M6S1P1, CA
2994 Bloor St W, Toronto, ON M8X1C2, CA
2995 Bloor St W, Toronto, ON M8X1C1, CA
Green Mango at Royal York and Bloor is pretty good. There's also an Italian and Greek place along there. It's been awhile since I've been to the Greek place. I remember it being standard, passable. I only had a drink once at the Italian place so I can't comment on the food. There's also Rocco's Plum Tomato on Islington near the Queensway. Also haven't been there in about 10 years, so I can't comment on what the food is like there today.