Places to hang out 7 nights a week: Where to go?

[Outsider]

I've got a cousin coming down from the US next Feb. He's in his early 20s. and is a bit of a ladies man and likes going out often, so he's asked me to find out what some of the happening spots are in the downtown TO core for hanging out/meet women every night of the week.

I've been out of the game for the past 10 years, so I thought some of you may be able to relate, and help me out with some suggestions...
What's the happening place for each night?

[Mattones]

Clubs and bars.. Since he is from the U.S take him to the rippers! he is 20 and in tje U.S you have to be 21. he will love it.

[matdwyer]

a site like clubzone.com will have the places with themed nights - from experience though I can tell you most "bars" and "pubs" will be pretty dead sun-wednesday... they'll have your average drunk joe, but not ladies (this may be different for say between 6-9pm at the office type bars)

Other than that, you're SOL - also some of the bars close up early (12-12:30) on non big nights