louis, it depends on what your friend is looking for, his temperment/tolerance for different weather conditions and his sense of adventure. Even just looking to get l*id brings a ton a variables into the picture; young/old, aggressive/passive, his ability to communicate with those of a different language/cultural background, color/ethnic/language preferences, etc. Here's my humble view. Take it for what it's worth.
I hobbied intensively in MTL 5-7 years ago (I think) back in the "Heartbreakers days" as I call them. I found the city wonderfully charming both in architecture and the people. I've also spent the last 5 or so years hobbying mainly in Toronto. Toronto is much more "Americanized" but the familiarity sometimes is comforting. I've never been to Van Couver, I can only repeat what others have mentioned to me on and off the boards.
Culturally, I loved the Quebecoisse seeming passion for getting out and conversing and partying with friends. I liked to walk around and check out the people on the street. I also sat in restos and bars and watched the interaction between the patrons. To me, it was an adventure.
I only know a few French phrases -- my most important ones have been: "Parlez vous Anglais?", "Merci" and "Bon jour/bon coir" -- and have gotten along swimmingly. As for the arts and other things, I was a little intimidated at times but mostly everyone was accommodating to the stupid Yank.
Gastronomically, Montreal was wonderful. Most restos I ate at had things I would have a hard time finding anyplace else and it was reasonable and delicious. Rue St. Laurent beckons me still.
The weather? Well, I've only been there between October and April so it's usually cool or damn cold with the wind off the St. Lawrence. That still did not stop me from getting out and about (mostly on foot or by cab) if you dress for it. They also have the underground if a little shopping is in order.
As for the women. Indeed, the ladies of MTL are absolutely gorgeous. There is what seems to be a higher proportion of younger women than Toronto. You'll also run into many more where conversation is strained to non-existant because of the language barrier. The way around it is to ask before ordering from the menu. Or, as I do, take your chances. Overall, I found the MTL ladies to be more passive -- some terribly so. That does not work too well for me so some encounters were less satisfying that I had hoped. Now that I'm a little older, that may not bother me so much although I do like "participatory sports" more than being the "only athlete on the field". Prices are definitely lower overall but the range is still there.
Toronto, as I said, is much more Americanized. The people are less open (until you get to know them) and it is a much busier lifestyle. There is much more to see and do if only because the non-existent language barrier intimidates me less.
Food-wise, there are plenty of awesome places to eat but they are more work to get to since they are spread out more over the much larger metropolis. I would the range of food styles are a little more limited but it's there if you're willing to hunt for it.
The climate is more temperate than MTL but it can still get damn-cold in the winter. I've been there year-round and never had a problem with the weather.
Women-wise, there is a much larger selection of "types" than in MTL. This includes more BBW and EEs. The general escort population seems to be in a slightly higher age bracket. Personally, I prefer them somewhat older with the 30s being my favorite age bracket. They bring more varied life experience into the picture which, for me, has resulted in more conversation than I had in MTL. Also, the women I've seen in TO have been more aggressive (read that as involved) in what was going on around them including taking the lead where it suited them. Price-wise, you start at a higher point than MTL and go up from there.
Now, we also have Ottawa -- forget it: slim-pickings for any quality. Could it be the MPs have hoarded the best? LOL!
Kingston -- non-existant.
Niagara Falls and environs: There are a few great providers and agencies in the area but, because of the lower population density, the variety is much less. You can still hook up with some interesting women. Prices are between TO and MTL. It's also a touristy area in the summer. Wintertime the place seems more like a "working town" and the cultural activities, for the most part, are closed.
Where would I go? I'd still love to get back to MTL if I had the chance and update my experiences. However, either TO or MTL would be a fine destination.
Joie de variété !!