Come, my little parakeets. Let me show you the way to frugal flirting:

Dinner at a Chinese Restaurant

Dates almost never order liquor with their beef & broccoli.

Volunteer at a Soup Kitchen

It's hard to not look good while surrounded by hobos asking for more saltines...

Pottery Painting at 'Color-Me-Mine' or 'My Name is Mud'

Impress him/her with your bowl-painting skills and skip right to desert. If you're lacking artistic prowess, paint "This is a wonderful date. I really appreciate you as a person." For extra points, have desert served on your new pottery.

Bowling

Nobody can stand more than three games. If you've got some skill, bet him/her the price of the lane. Extra points for granny-style.

Win a night out in a Radio Contest

50% of the time, the answer is "Video killed the radio star"

Go to a Museum

Remember, the donation is just a suggestion! Wear a turtleneck, it'll make you look sophisticated...

Plant Hair in Your Food

Long strands work best. Make a big fuss. Mention your sister at the NY Times.

5$ Footlongs

Mostly because I like the song.

Eat Lunch at a Bar

They're so desperate to get people in there during the day that you can score some serious specialiage.

Create a Scavengar hunt

Have your date make a list of 20 random things and spend the rest of the night finding them. If they're successful, offer to see them again.

Lasertag

Minutes of fun and lots of dark corners...

Test-Drive Expensive Cars.

Wear fancy clothes and act really confident--Sometimes they even give you free stuff! Leave fake contact information.

Hole-in-the-wall

Take them to a really cheap, greasy restaurant a bit of a distance from where you live. Claim you researched hip, underground joints on Yelp. This works particularly well in New Jersey.

Get Free Groceries

Order groceries with your roommates from one of the online services (Fresh Direct, Dagostino's) that gives you $50 off your first order. Don't tell the roomies about the discount.

Somewhere Expensive

When the check comes, reach into your pocket and FREEZE WITH SHOCKED LOOK ON YOUR FACE. Hold for 7 seconds. You forgot your wallet. Get upset. Offer to pay for the next two meals. Continue to joke about how stupid you are throughout the night. This may even be construed as charming... if you continue dating, make sure the next two meals are less than half the price of this meal. If not, then you just scored yourself some free grub, player. .