As to finding a great place to eat in T.O, like Chicago, they say that if you want, you can eat at a different restaurant every night and never have to hit the same place twice. A little over stated perhaps, but yeah, there are a gazillion places to choose from, and more popping up all the time. As to hipsters and vegans, ... .... .... trust you're making new friends, mate (it's a big city, over 3 million live in the place, with another 5 or so million within driving distance (toss in Upstate NY and Montreal ... hey, there's an idea: head out to Manhattan or Montreal for a night on the town, great fun to do when solo, and all your friends may wisen up and take you out on your special day or eat with you at least, sheesh).
Uh, as to places in T.O, what are you into? If you're just looking for a great meal, head out to Anthony's or the King Eddie downtown, or uptown to Yorkville (there's a resto in a house up there, steak and wine list is good (at least it used to be), then bop over to Yorkville proper for some martinis, etc. If it's low key you want, head east to the Beaches - a little place on Queen just east of Woodbine called Whitlocks, also good steak and a decent wine list. Can hang out with the hipsters after at one of the local pubs (tell your vegan friends they make good salads, and drag them along ... OR, can do the entertainment district, there's some great (and not so great) restos down there (all the rage/trendy thing, right?). If you like steak, Ruth Chris is there, then can head out to the clubs or whatever for a night club. All depends on what you want: fun to play tourist in one's own town and see what's what, I agree. There are also lots of piano bar/martini places, if prefer over a loud night club. Of course, can also head over to the theatre district and take in a show, or do anything you want - it's your special night, afterall (and hope it was fun).