It takes a lot of courage to ask someone to date you, especially in this day and age and how we tend to hide behind technology and texting. If you really want to stand out, and ask a girl or guy on a date, then separate yourself from the “norm” and pick the sweetest, most memorable way to do so! 

The little things like your method of asking can change your dating game, and it’s important to know the little tricks that will work in your favor.

Here are different playful, lighthearted ways to ask someone to date you

date you


One way you can ask someone to date you is by calling into a radio station, and telling your guy or girl to listen, because you have a surprise for them. Then, once you are on air, you simply ask them if they will go out on a date with you. Voila!

Become a comedian

Laughter always wins, and it might just win you a date! Think of a funny comedian you like, or better yet, one they like. If they don’t have a favorite comedian, then find out what their favorite comedy movie is, and learn to recite the funniest lines to them as part of your way to ask them to date you. How could they possibly be able to say no?!

Write a song

If you don’t want to learn funny lines from their favorite movie, another way you can ask them to date you is by using the power of music. You can write a song for them! If you want to make it romantic, or comical, that is totally up to you. Use that kind of idea to get your creative juices flowing, and write them a song to ask them to date you.

Don’t take no for an answer

One way to get your way is to not accept no for an answer. You can ask them to date you over and over again until they say yes. Sure, some might think this is a bit insane and ridiculous, and also wonder why you would want to go on a date with someone who doesn’t want to go on a date with you, but hey, whatever works!

It is possible that if you ask them enough times, they will get tired of saying no, and eventually say yes, just because they want you to stop asking. And who knows, they might even have a great time with you on your date, assuming when they eventually say yes, they actually mean it.


We all know the way to a man’s heart is through their stomach, so if you’re a girl wanting to ask a guy out, this one is for you. Bake them something. Ideally what you to bake would be their favorite dessert or you can keep it basic with something that everyone loves, like brownies or chocolate chip cookies.

If you bake them a cake, for the frosting you could write out “Will you go out with me?” or something along those lines. If you don’t have enough room to do so, then include a note on the side that asks them out. Not only do they get to eat a sweet treat, but it’s also super sweet that you would take the time to bake them something!

Mail them a letter

If you don’t feel comfortable asking them out in person, then a great way to get all your feelings out on the table and ask them to date you is by sending them a letter. The power of words is a true thing, especially when it comes to confessing how you feel for someone.

If you write a letter, don’t make it too cheesy, because you don’t want to sound like you’re copying something out of a Hallmark card. But do make it personal, and make it worthwhile. Let them know how awesome you think they are, and they will want to go out with you for sure.

Use a mariachi band

I don’t know what it is exactly about mariachi bands that make people think of love, romance, and all sorts of mushy things, but they do. One creative way you could ask someone out is by getting a mariachi band to back you up.

So if you are in person with them, and wanting to ask them out, have the mariachi band start playing behind you, and use that momentum as your courage to ask them out. In a perfect scenario, they will say yes, and then the two of you will both be ecstatic, all the while dancing to the beautiful sounds of the mariachi band performing. How romantic!