Lady Smarts: How to Date for $20

Written by Meredith Russo on . Posted in NY Press Exclusive.


Stacks of cash not required.

Dudes, don’t let a tight wallet keep you from love, or something like it.

How to impress a lady on a first date for under $20:

  1. “Forget your wallet.”
  2. Feign upset and embarrassment.
  3. “Find $20 in your pocket.”
  4. Feign relief and good fortune!
  5. Resolve to have The Best Date Ever using this, and only this, $20.
  6. Blush when your date finds this playful and endearing.
  7. Congratulations, now you can shamelessly make a game out of being cheap and seem all the more fun and creative for it.
  8. When choosing a restaurant, think: small plates. This translates to lots of ambiance and little portions, so you and your date can share a spoonful of garnish for $13 and still have enough left for their cheapest, finest table wine.
  9. What? No table wine?! Then you can forget about a tip!
  10. (You didn’t have enough for a tip anyway.)
  11. Flirt with the waitress while your date is in the bathroom. Ask her if she thinks the date is going well. Look cute and nervous.
  12. Keep pushing the (tap) water on your date. New York’s finest! Roll your eyes at the waitress as she visits the Ladies Room yet again.
  13. Explain your embarrassing(ly scheming) situation to the waitress. Maybe she’ll take pity and bring you free drinks. Your date will marvel at your power of persuasion and won’t even notice that you’ve been hitting on the waitress all night.
  14. After a few sips of wine, tell your date she seems drunk – in a cute way! – and that you really appreciate her low tolerance. People have such high tolerances these days!
  15. So now your date is done drinking for the night, but what should – hmm, is that her stomach growling or yours? Damn that garnish was light. Baby Cornish Game Hen Parsley Wraps sounded so hearty.
  16. Don’t panic. Ask for some nuts to level your blood sugar. Blame it on your “diabetic” date during her next bathroom break.
  17. Now that you’re thinking clearly, provoke the steaky guy at the table next to you.
  18. Bump his chair and insult his girlfriend under your breath when you walk by. Then deny, deny, deny.
  19. Enjoy the free duck spring rolls that come as a sorry-you-were-assaulted-in-our-establishment consolation dish. Make sure tax and gratuity are added after that’s been comped.
  20. Request some extra mango dipping sauce, for your date. Who cares if she’s sitting right there and didn’t ask for it? She’s super picky.
  21. Okay, so things aren’t going so well anymore. Your date is feeling violently ill from overhydration and wants to go home.
  22. All is not lost! Once you walk her to the subway – and ask for a MetroCard swipe – you can return to the restaurant, sit at the bar, and flirt over free drinks from the waitress.
  23. Two dates for under $20? Now I’ve really outdone myself.

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