I Dare You to Date Yourself

If it’s not clear, I’m all about challenges. I’m humble enough to accept that I struggle with discipline, and aware enough to acknowledge that my pride will want to win any challenge, which results in me being consistent far longer than I would on my own.

This February, I’m challenging you to something that may be quite drastic, but I guarantee will be well worth whatever adjustments you make.

The challenge is simple – for an entire month, I dare you to date yourself.

Your challenge will vary based on where you are in your relationship with yourself. If you’re just getting to know you (and that’s fine – some people go through their whole life without getting to know themselves), this starts like any other new relationship: questions.

You know those annoying questions you ask someone you like when you first meet them? Their favorite color, and favorite movie? Skip those. You should know those things. Start deeper, but don’t get so invasive that you scare yourself off. 

This all sounds crazy reading, I imagine, because it feels a little bizarre writing it. But, trust me, it’s true. If you go too deep too fast, you’ll reject yourself without a second thought. You’ll easily convince yourself that this stupid challenge is beneath you, and disregard all of this.

It will be as awkward and uncomfortable to ask and answer these questions yourself as it is to do with a stranger. A part of you will want to avoid this whole thing altogether, because the exercise itself points out that you do not already know these things, and maybe you assumed you would by now. It can be embarrassing.

Here are the first questions to answer (in voice notes or journal entries, whichever works better for you).

1. What do you like to do for fun?
2. If you could live anywhere, where would it be?
3. What’s a perfect morning look like for you?
4. When was your last vacation? Where did you go? What did you do?
5. What’s your dream life look like?

These journal prompts are one part of the dating, but don’t forget about the other, more obvious ones. I’m not going to sit here and act like I’m making this up. You know how you behave when you’re dating someone you like. That’s what I’m daring you to do.

Get cute. Actually, keep yourself cute. You know, ‘stay ready so you don’t have to get ready’. This month, put a little more effort into your appearance. Even if you work from home, do your hair, get dressed, spray on some perfume. Do your skincare routine, the long one with the expensive products you ration. Wear your lingerie. If you don’t have some, get some.

Go on some dates. And make it worth your time. Research the best spots, pick out an outfit, take a mirror selfie before you head out to remember how cute you are. Take yourself to the spa. Make a point to see the sun set and rise as often as possible. Buy yourself flowers. Write yourself notes. 

Treat yourself like you’re special. Again, it feels weird reading this, right? Because you do think you’re special. I know you do. The challenge is to make sure you’re putting the actions behind those feelings. You say you love yourself? Prove it. For an entire month, act like you love yourself. Act like you want you to fall in love with you.

You may be in a good space in your relationship with yourself. If so, go you! You’ve been putting in the effort and it’s paying off. I’m happy for you. In this stage of your relationship, I challenge you to do everything listed above with different journal prompts. I hope these push you.

1. What is going right in your relationship with yourself?
2. Is your life set up around your work, or is your work set up around your life? Do you prefer it this way?
3. What’s a dream adventure you’d like to go on?
4. Write about your happiest moment in recent memory.
5. Is there anything you need to forgive yourself for? What’s holding you back?

I can’t guarantee any results from this challenge. I don’t know how answering this dare will affect your life. But I don’t think there is any bad that can come from treating yourself better. So, that’s it. That’s the challenge. I dare you to date yourself from a month. Are you in?

If you need a little assistance with the challenge, use my self love guide I created for February. There’s a self care daily habit tracker, date ideas, and stationery to get your life on track, which is the best self care. You can’t relax enough to dream in chaos. Download the guide here.

XOXO