I don't know if it counts as a hole in the wall place but I really like BarChef for cocktails. Your friend will be into it I bet. Pravda Vodka Bar is also an interesting spot for a drink.

One of my own go-tos for evenings in Toronto is The Rex Hotel Jazz and Blues Bar for some pints and jazz.

Cold Tea at 60 Kensington in Kensington Market Speakeasy bar, difficult to find but worth it. Great vibe, Dim Sum served as 'bar snacks'

Hi, you should try The Madison Avenue Pub It has nice cocktails and the music is great.

For a hole in the wall place with great cocktails, you've got to go to Cold Tea. It's on Kensington Avenue, in Kensington Market; to find the actual bar, you have to go through this tiny Chinese mall-like hallway, and then near the end of the hallways there's a big grey door on your left. It's a little confusing, but definitely worth it.

The Black Hoof on Dundas West is also great, though definitely somewhat more upscale. It's still got character though, and prices are pretty close to the city standard.

There's lots of other things to do at night depending on your tastes. More upscale lounges down on King Street, the clubbing district on Adelaide Place, dive bars and pubs on Little Italy, Ossington & Bloor. There's also tons of live music and other events going on in the city regularly.

I can say MR. GREEK Mediterranean Grill which is affordable bar to hangout and is chill.