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last Q, fun place to eat with good ambience that turns into a night spot?

my sister just graduated from university and we will be visiting her for christmas. My husband and I want to take her out on saturday night. can anyone recommend a place with great food, fab ambience that is a good people watching spot?

I want somewhere that we can eat, drink and drink and people watch. Do restaurants turn into lounges at night in TO?

I would ask my sister, but she works for a non-profit and makes minimum wage, so she doesn't go out a lot.

Thanks!

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  1. a little more criteria..somewhere trendy. my husband and I are 28 and 25 and my sister is 22.

    We eat everything...sushi, italian, indian, greek, american, canadian etc.

    The only thing i would not want is chinese, because we're spending sunday and monday with our parents eating nonstop shanghainese food.

    1. Some suggestions for hipster hangouts: Czehoski's, The Drake, Doku 15. Or you could hit College Street as there are lots of options for both drinks and food and its always a lively scene. Maybe dinner at Coco Lezzone and then drinks at Wild Indigo afterwards.

      1 Reply
      1. re: midtowngirl

        I second Doky 15. very trendy and good drink menu

      2. For a trendy lounge with good food, I'd suggest Laide. Great tapas menu. But as the name suggests, it's not for the overly timid.

        1. Oasis, 294 College Street, Toronto Phone: (416) 975-9594. Great ambience / lounge near U of T. As for "people watching", it's a small place and you can't really sit outside in the winter do you are limited to watching the people inside.

          2 Replies
            1. re: Herb

              I had no idea... I used to throw spoken word / hip-hop jams in the backroom there. What is there now, and any idea why it closed?

              Thanks.

          1. Habitat, Coca or Czehoski - all on Queen W.