Copy/ pasted from my "Ask bobistheowl!" thread on another board, (November, 2014), here are some tips on how to meet civvie women in a big city:
Q: OK, bob, this is the thing. I'm too old for clubbing, in any decent amount of light. I don't want to have to resort to the ice cream aisle. I'm tired of reading about other guys having sex. Where should I go, to find various types of civvie women that might find any of a number of us pathetic guys at least worthy of coffee? - Yu, Shanghai
Yu, a man's best friend in choosing, rather than being chosen, is lack of visible competition. Women are often interested in the best man who is there, rather than the best man who there is.
If you're looking for a standard '5', in any of a number of different shapes, sizes, and age groups, you could get tickets for one of those local women's talk shows. Every station has a couple of them, The View, with different hostesses. You're going to be the only guy in the audience, so that automatically makes you the best looking guy there, if only for a little while, until other guys start doing it, too.
If you want sleazy in an attractive way, try to get tickets for one of those lowbrow talk shows in the Jerry Springer vein, with the paternity suits, or the plot of a MILF smut clip. A lot of guys are already working that field, so wear a clean baseball cap, and tuck in the mullet, it's not the 90's anymore.
If you're looking for someone a little more refined, try Sunday afternoon around 2:00 PM at the ROM, or the Natural History Museum closest to you. You'll find the younger single moms in the dinosaurs section, or near the mummies, or cave man dioramas. You'll know she's single, because if she weren't, she would be making sandwiches and bringing beers to the guys watching the game. If you just want a quick fling with a brainy single, go to the armour section, but be careful; the permafrown crowd congregates there, too. How to spot them is another lesson.
If you wanted to have a few drinks with some of the women who don't go to bars to drink with men they don't know, it might be a good investment to take a Learning Annex wine appreciation course, on a Friday. If you don't meet anyone you like, take it again; most people don't take that course twice, unless they want a clean slate.