How to Ask Someone Out and Feel Great About It

February 28, 2023

One thing that stops a lot of people from asking someone out is the fear of rejection. I get it. It’s a nerve-wrecking experience. I’ve been there too.

What if you can get yourself to feel that the rejection doesn’t even matter? Wouldn’t that be great?

Here’s a little secret tip to asking someone out:

Simply make interesting plans for yourself (that you want and will actually go for!), and invite that person to come along if they want to.

You can text that person something like “Hey, I’m going to check out this free art exhibition at 2pm this Sunday. Feel free to join me if you want!”

The keyword here is “yourself”. Make sure you are actually making plans that you enjoy and will proceed even by yourself.

How this approach works:

  • Even if the person doesn’t show up, you can still proceed with it by yourself (which is supposed to be your original plan anyway) and feel good about it. Remember, the plan requires only one person to proceed. The rejection truly does not matter.
  • There’s no pressure for the person to agree to join you. This approach gives them an easy ‘out’. You won’t come off as needy.
  • The person will join you if they are interested in your plans and want to make themselves available for it. If they aren’t interested, then it’s a win-win for both sides since this probably shows that both of you have very different interests. In which case, both of you might as well continue doing different things separately.


Asking someone out can be intimidating, but it's also an exciting opportunity to connect with yourself, and with someone new. No matter what happens, it's important to make sure that you're enjoying yourself!

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