We get that it can feel risky to ask someone out on a date. But it doesn't have to be a big, intense thing. Instead, make it playful and lighthearted. We have all sorts of fun and creative ways to ask someone out on a date that could get you the yes you're hoping for.
Show Them You'll Make Beautiful Music Together
Love to kick it old school at a record store or CD shop? 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 share your respective finds into each other's playlists.
Walk On
Everyone likes to be complimented on their taste. Politeness can easily be segued into flirting and, thus, creative date-asking ideas. If you see someone wearing a particularly snazzy pair of shoes, tell them they look great. If they seem to want to continue chatting, ask them if they're comfortable for walking because, if so, you'd love some company as you walk to wherever you have to go.
Old School Telegraph Your Intentions
If you feel like spending a little cash and you totally want to kick it old school, 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.
Star With a Cinematic Beginning
Are you both classic movie buffs? This creative date-asking idea will take some time, but go online 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 a movie. Of course, you will have to concoct an ending for the story.
Invite Them Into the Fold
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.
Show Them Your Sweet Side
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.
Say It With Fruit
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.
Make Your Intentions as Plane as Day
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.
Hunt or a Connection
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.
Make Asking Them Out Fun
Show your fun side to potential dates by making your ask entertaining. It'll let them know that spending time with you is sure to be great fun.
