Creative Date Asking Ideas

man asking smiling woman out

Whether it's an attractive stranger, a classmate, a colleague or a friend, when you want to step it up but don't want to use the same old pickup lines, you're in need of some creative date asking ideas.

There is no guarantee that any of these will work, but if you try one, at least no one will be able to fault you for being cliché.

A Few Creative Date Asking Ideas

  • Tell the person in question that you just heard a great song on the radio and now you're all fired up to go on a music-buying binge. Would they like to wander around an incredibly cool independent music shop with you? Maybe later, you could download your respective CDs into each other's iTunes.
  • Everyone likes to be complimented on their taste. Politeness can easily be manipulated into flirting and thus creative date-asking ideas. If you're a guy who sees a woman wearing a particularly snazzy pair of shoes, tell her they look great. If she seems to want to continue chatting, ask her if they're comfortable for walking, because if so, you'd love some company as you walk to wherever you have to go. Likewise, ladies, if a guy is wearing something sharp, let him know you think so and suggest that the outfit in question would look great at a coffee shop you like and would he and his good clothes like to join you there?
  • If you feel like spending a little cash, try sending a telegram. That has novelty and is fun. Add to the retro feel by noting in the telegram that the person should meet you at the most historic building in town.

Go the Artsy Route

  • Are you both classic-movie buffs? This creative date asking idea will take some time, but go to the Internet and search for still images from some of the films you both like. Piece them together using quotes from the same film to tell a little story. Perhaps it's just the beginning of a story and if they want to hear the rest, they'll have to join you for dinner and an aural movie. Of course, you will have to concoct an ending for the story.
    • If you want to show off how sophisticated you are, this same trick works well with Shakespearean quotes or clips from operatic arias.
  • If you, or someone you know, can do origami, make the person an origami piece that's meant to come apart. Make a clearly marked tab so that they know to pull it open. When they do, you'll have another piece of paper inside asking them to step up from a paper conversation starter to a personal connection.

Go Wild

  • Here's a "sweet" date-asking idea. Do you work or go to school with someone and know that they really love a particular muffin or other baked good? Buy one for them, cut it open and insert a note asking them to come to the bakery with you next time. Close it back up as best you can and then attach a note via a toothpick telling them to cut open the muffin at that spot.
  • You can also spell things out with food. Use blueberries or sliced strawberries to write "Date Me?" on a plate or pancake. Even if they say no, at least you've given them some nice antioxidants.
  • If the person is someone with whom you have a very jokey relationship already, use that to your advantage. You can do anything from sailing a note asking for a date via a paper airplane, or attaching a note to a jack-in-the-box and leaving it for them to unwind. Bear in mind that these only work if you already know you both have a similar silly sense of humor.
  • A scavenger hunt can be fun. If you saw the film Amélie, you'll remember how the heroine laid out a series of arrows and notes for the man she loved to follow, guaranteeing his interest. You don't have to be that elaborate, but a little series of notes asking the person to keep looking in another area until they get to the note that asks them out, which is preferably being held by you, could be very charming and fun.

However you choose to ask someone out, just make sure that you do ask. Yes, it will hurt the self esteem to be rejected, but at least you tried.

Creative Date Asking Ideas