How to Gain Confidence and Ask Your Crush Out


It’s easy to think of a million reasons why you shouldn’t ask your crush out, such as: “She’ll think I’m an idiot”

“I’ll be so embarrassed when she says no”

“I’ll have to see her every day after she says no”

“Her friends will make fun of me”

“My friends will rib me for getting rejected”

And so on.

The tough part is building confidence to surpass these reasons and just going for it. When I am working with male clients, I let them know that it isn’t just building self-esteem in the area of asking women out, it is finding ways to build confidence in every area of your life. I call this “spending more time in the zone”. Through coaching, we first look at activities you are currently doing in your life that you feel confident at. For some men, this is hard and is a real eye-opener that they don’t really feel they are good at anything. In these cases, we start small with perhaps one subject they were good at in school or one way they helped a friend or family member. These are things they are good at and potentially proud of. Then we discuss why they felt good about themselves at the time to help in narrowing down the key attributes for them to be “in the zone”.

For example, a man named Rob who does not spend any time in the zone will wake up, grumble about his day, get through work by counting down the hours, head home, watch TV or play video games and go to bed. Rob wonders why he doesn’t feel good about himself and has zero confidence around women when it has so much to do with how he schedules his day.

To help in building self-esteem, Rob needs to have a day more like this: wake up a bit earlier than usual, throw his runners on and get out for a 30 minute jog, eat a healthy breakfast while listening to his favorite music, write down a positive affirmation for the day, get dressed in some clothes he feels good in, listen to some uplifting music or audio books on the way to work, commit to focusing on the positive aspects of work, head to a co-ed activity after work such as a sport or interest group, head home to a healthy dinner and a good night’s sleep.

Notice how I haven’t talked about asking your crush out yet?!

This is because you need to spend a good amount of time in the zone before you can translate that confidence to your interactions with women. And here are the cheat notes, while you are spending more time in the zone, you can “fake confidence” with women. This is completely okay and in fact, can be endearing and charming to women.

In preparing to ask your crush out, set the stage in a way that works in your favor. Choose your mode of communication based on what has been most common between the two of you up to this point. For example, if your crush is someone you have only spoken to in person a few times, don’t ask them out via email or text. If your communication has mostly been via Facebook or email, and in-person sightings are rare then ask them out via Facebook or email.

Here’s an example of something you can say and you can adjust it based on whether it’s email or in-person, “Hi Cheryl  - I hope you are having a good day – I wanted you to know that I’ve really liked our conversations over the last while and I’d like the opportunity to get to know you better. I was thinking that perhaps this weekend, I could take you out on a date? Let me know which evening or day works best for you.” This encompasses all you need – you pay her a compliment and you give her options on timing. You’ve done what you can in asking her out in a gentlemanly way and building up your confidence in order to do so. Good for you! And if she’s a good fit, she’ll say yes and if she’s not a good fit, you’re free to move on to someone who will be a better suited (hint: someone who is enthusiastic and doesn’t need any convincing on how great you are)

To your authenticity,

Love, Christine

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