Island Foods on King just east of Dufferin has the best boneless
chicken roti I have had in my life. Two people can eat for a little over $20 depending on what you get. It's a cross between fast food and a sit down place. You order and pay at the counter and they are licensed so you can have a beer or whatever with your meal but I usually stick to my diet coke and a bottle of water when I eat there.
The Bright Peal in Chinatown (it's on Spadina but you enter on a sidestreet then go upstairs to the restaurant) has the best Dim Sum! They serve it the traditional way with the carts. The servers bring the carts by your table so you can take what you like. The tea they serve is wonderful too and I've always left there feeling well taken care of and of course well fed. The last time I was there it was just my daughter and I (we were having a girls day in TO) and our meal was $25 for the two of us.
For pub grub I like the Elephant and Castle on King Street West, and also the Brazen Head on East Liberty Street. The Brazen Head is a little more expensive than the Elephant and Castle but still it's nice.
We went to Shoeless Joe's on King east of Dufferin a few weeks ago for the first time and I was pleasantly surprised. We were a table of eight and I know that big tables can be a challenge for the kitchen and servers but they handled it well. The kids' food all came first and that was fine with us, and then not even five minutes later the adults' food arrived so we were all eating at the same time. Prices were reasonable and the only thing you need to bear in mind is that it's a sports bar so the experience in the evening would be very different to what we had at lunchtime.
The Old Spaghetti Factory on The Esplanade has always been a favourite of mine. It's one of the places my husband and I used to go to when we were dating and then when we had the kids we loved taking them there for dinner. Prices are reasonable (around $20-25 per person) but I haven't been in a few years so I can't speak to the food quality today.
For fine dining I would suggest:
-Ruth's Chris Steakhouse (on Richmond West in the Hilton Toronto Hotel) Prepare to spend at least $100/per person but the food is amazing
-Harbour Sixty Steakhouse (on Harbour Street, just past the off ramp from the Gardener Expwy) Again you're looking at at least $100 per person just like Ruth's Chris. I prefer the side dishes that Harbour Sixty offers compared to that of Ruth's Chris but both are equally good.
-Rosewater Supper Club at 19 Toronto Street is an amazing venue and I recommend it for that alone.. we have been there a number of times and the quality of food and service has been varied. I tend to order
steak when I eat out so for me my dining has been good but we always go with the same group of people and others in our party have had disappointing meals at times. Plan on spending at least $100 per person to dine here as well.
So there are my suggestions....