I think every guy over the age of 21 should have ONE woman in his life he is happy to spend money on to share dinner with once a week. It doesn't have to be a love/sex interest... Could be your mom, sister, daughter or someone else that's not a woman...
if a woman is a prospect I'd invite her along on something I'm going to do anyway. The Newspaper is full of free events like music in the park, Gallery shows, happy hour specials, Farmers markets, etc.
My "date nights" ended up being Wednesdays and Sundays after training runs believe it or not. We'd grab beers after 3 miles on Wednesday, and Sunday's long runs we'd go watch football at the sportsbar. I'd literally meet a woman right after a run and make plans for a date that night. I'd shower, then meet her in the early afternoon. Too early for dinner, maybe a picnic in the park. Post run excuse to go for a hot tub would have been perfect in this case since it was technically a second date.
'nother date idea... go to the Horse racing track, bet $2 per race, pay 5 bucks for grandstand seats. Lots of movement as you go to the saddling paddock to look at the horses, she's always looking over your shoulder at the racing form, great kino...
Summertime - County fairs. Food is gonna be Muey Expensive this year. Eat before you go. Meet in late afternoon near a grocery store with a deli. Share a 12 inch sandwich for a late lunch/early dinner. grab wine in a can. Picnic.
Bar Trivia nights. Especially midweek.