5 steps to build up the courage to ask your crush out

So you like someone, and you’ve been thinking of asking them out. Maybe you even hinted that it “could be fun” to “hangout” or implied that you may do this or that “next time we meet.” 

That’s a start. I celebrate you for that!

What you did not manage to do so far is boldly ask that person to go out with you, decide on a thing to do, and set up a time.

You’re kind of overthinking it. You don’t want to seem pushy, or undecided, or uninterested, or over-interested. Whenever you write something, you find yourself deleting your message and ruminating on it for some time before giving it another try.

If this goes on, you fear that you may still be single and hopelessly in love with your crush when you’ll be giving a toast at their marriage in 5 years. Okay, now I’m kidding, but you get the idea.
It may be time to consider that the issue is not in finding the perfect, foolprof combination of words sent at the exact perfect time to get a “yes”. What you need it to feel good enough about yourself that you send that message and get a clear answer.

Ever wished there was a simple way to build your confidence and break free of the anxiety to ask someone out? Then enjoy this step-by-step approach to asking someone on a date like a respectful badass.

Step 1: the disaster-proof checklist

First, let’s make sure it is appropriate to make a pass at that person and that it won’t bring chaos and heartache to your life. Also, let’s make sure it’s easy to say no because the last thing you want to do is second-guessing why you got that date.

  • Are they open to dating? If you know for a fact that they are, great! If you have some doubts, don’t let that stop you entirely but be extra considerate. 
  • Do you have any preexisting associations that you wish not to disrupt? The ground rule is to steer free of people you wouldn’t be able to avoid if things were to end up poorly. Not just for your sake, maybe they would want to avoid you too. Imagine breaking up with a coworker and having to see them every day. 
  • Is there any power-dynamic in place? Especially if you’re a heterosexual male dating females, being mindful of the things making it harder to say “no” is the most considerate thing you could do. Women are often brought up to be pleasing and may have a more challenging time to say no, especially if you are her boss or a patron at her place of work.
  • Is there an age gap big enough to create a toxic power dynamic? The older you get, the more significant the age gap would need to be to have some consequence. A 30 years old dating a 20 years old is way more creepy than a 50 something dating a 40 something. The medium age-gap in marriage in 2019 is 2-3 years old if you want some idea of what’s going on.

Step 2: take the pressure off.

Good job! Now that you’re confident that it is appropriate to ask, you can relax. 

Now there are usually two main pressure points at this stage: fear of rejection and overwhelm.

If you’re afraid of rejection, remember that it’s tough to find someone that feels like a good fit as a romantic partner. That bond is so unique and deep and it’s rooting in many aspects of you, like your relationship style, values, sense of humor, and even your smell. Some things about you could feel foreign to someone and delightful to someone else. It has nothing to do with your perceived “value” on an imaginary “dating market.”

You probably have friends you would not want to date and still appreciate a lot.

If you feel like all of your future is in the balance, remember that it’s a date and not a marriage proposal. Your future is impacted by many decisions you take daily, and unless you suffer from anxiety and need the help of a therapist, this should not prevent you from taking action.

What you are offering is a shared moment, preferably a nice one, to see if you could maybe try a different relationship.

It doesn’t have to be the perfect venue, or super expensive, or otherwise impressive, as long as you get an opportunity to know each other on a deeper level and show yourself as the charming date you are.

Yes, you are! We’ll talk about that later.

Finally, remember that you won’t have to do it again if you do not enjoy yourself. The worst-case scenario is probably two awkward hours and a funny story.

Step 3: Embodied breath to feel like a badass

Try 5mn of deep, relaxed breathing in your lower belly. If you want, you can choose to breathe through your mouth for a deeper connection to your root and sense of being grounded. Feel yourself supported by the hearth and connect to a sense of safety.

You can also connect to your potency and sense of strength. Relax, feel good about yourself. You got this.

Step 4: Internal and external validation

At this point, you should already feel pretty good about yourself, so it’s the best time to make *the list*. Think of everything that makes you a great companion and everything you love about yourself.

You can even write it down and keep it around, in a place where you’ll see it every day to boost your confidence.

If you have a compliment squad, let them know you need some of their good vibes. If you don’t, consider forming one, but later. Don’t let that stop you now. You’ve come this far!

Step 5: Do it now!

Take your phone and send that message, or even better, do it in person.

Don’t wait for “the right time”, it is now. (make sure your target can talk right now and that’s it).

Be specific; make sure the time and place are clear and work for both of you. If you can’t mark it in your calendar, you haven’t got a date; you just made a plan to maybe hang out someday. 

You can take another chunk of pressure off by reminding yourself that it’s a proposition, and some back and forth to work out something you’ll both like is acceptable. They already saw that movie? why not see another one or go to an exhibit? Not into thaï food? What about that veggie pace that has the best playlist?

If you’re considering to create a list of 10 options to make sure you have “the one”, recognize this as an avoiding tactic and go back to the embodied breath to soothe yourself.

Optional but super-fun step: congratulate yourself
You did it! You beat perfectionism and anxiety and sent that message! Whatever response you’ll get, you chose yourself, and it’s something not everyone is capable of.

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