Conversation Skills
For Men

Pass these 3 "checkpoints" before you ask her out

November 4, 2022
▪ 6 mins read

Avoid rejection with this smart checkpoints system

I get it. There are a lot of reasons why you might hold back on asking for her out.

You don’t want her to reject you...

Could the timing be better?

You’re not sure you’ve done "enough" to impress her...

Yes, not making a move protects you from experiencing rejection. It equally means you’re constantly putting yourself on the sidelines of dating, and are never going to have the experiences you want with women.

Did you know there’s a smart workaround for this and 3 key checkpoints you should pass through before you ask her out?

Developing a better dating process

Most guys approach the "how and when to ask her out" question back to front. Because she’s attractive it’s a foregone conclusion that you should ask her out. Then you start to sweat it out that if you do it the "wrong" way that she’s going to reject you.Instead of starting at the end, it’s time to develop a better process for your dating life.

From my programme, Attraction Point, you should know that attraction is your reason to approach her, but the connection is your reason to ask her out.

In short, unless she meets some minimum standards for how much she invests in the interaction you shouldn’t even be thinking about asking her out!

If you are always chasing after women, and never get the responses you want then I’d highly recommend you pause this blog now and go to watch my video on standards.

See it this way - unless she passes through these 3 checkpoints you shouldn’t want to date her. This means rather than going all-in at the start you read the situation better before suggesting a date.

Fearing Rejection?

There's nothing quite like dating to make you fear rejection. In fact, for many men, their fear of rejection is so profound that it stops them from taking any steps forwards to meeting her.

You may especially hold back around women if you feel like nothing, in your history of dating, tells you that making a move is going to be successful.

The problem is, you may have chalked up more interactions as rejections, than were actual rejections. Let me explain a few times when you may have felt rejected when something different was happening:

1. Women who haven't responded to your first messages on a dating app.

Dating apps are often male-heavy, meaning women can be inundated with messages. I know this sounds like a high-quality problem to have, but in reality, it makes it hard for her to have the time to respond, and to figure out who's the right guy to go on a date with. If she doesn't get back to you, don't take it too personally. You don't even know if her profile is active.

2. Women who you once felt you had a connection with, but now who seem really aloof.

It's hard not to get sucked into the spiral of chasing her. But if she's not actively connecting with you now in a meaningful way, she shouldn't be making it onto your list of women you'd want to date. (And yes this involves a serious abundance mindset, more on this later.)

3. You've only interacted with this woman as a "business contact" or friend so far and she's taken aback when you ask her out.

To dodge rejection it can feel safer to "fly under the radar" and forge a relationship with her under a different pretext. However, this is usually unwise. Women can feel deeply uncomfortable when the purpose of your contact shifts in tone. Even if your intentions are good, they can come across at best as underconfident and at worst as underhand.Therefore, even if there was a degree of connection, if it wasn't established in the right context, it is unlikely to be reciprocated.

These scenarios can be avoided if you enter dating with a more realistic view of what she needs to offer. In this way, you can ensure that she is genuinely interested in you.

Checkpoint 1

She’s contributing to the interaction.

I know this seems like an obvious one but let’s look at some examples of where you might ask a woman out who isn’t actually contributing:

  • A woman who you don’t know on social media
  • A woman who is only responding to your messages with very short 1-3 word messages, or gifs.
  • Asking a woman out on a dating app with whom you’ve only exchanged 0-2 messages.
  • A woman you see in class, or in a coffee shop, regularly. Maybe a neighbour you’ve decided you’re attracted to.

With all these women your first job is to engage with her. See if she passes the other 2 checkpoints before you ask her out. Right now you are attracted to her, but there’s no connection to suggest you want to have a date.

(And in nearly all cases she won’t be open to going on a date with you).

Checkpoint 2

She’s giving you more information than you asked for.

After she engages with you, we really want to see the quality of her contributions.

Here are some good signals that you can look out for:

  • She might give shorter answers, to begin with, but as she becomes more comfortable she really opens up.
  • She’s happy to give you her first name if you’ve met her in real life.
  • She offers information you didn’t ask for (details about her life, preferences, what she’s up to etc.)
  • It’s also definitely a bonus if she tries to tell you something about herself that might impress you. Her work ethic, something she’s passionate about, a fitness thing she’s doing etc.

Unless she’s investing in the interaction she’s never going to meet your standards.

Remember if you want to raise your standards and stop chasing, claim your free cheatsheet on what standards you need for your dating life.It’s a super helpful short guide to get you started with this new, more confident, abundant approach to women.

Checkpoint 3

Once you’ve defined some qualities you like in women, then you can figure out if she lines up with what you want. The ideal moment to ask her out is after you’ve defined that she meets at least one of your standards. Before you ask her out you should be able to say, "I like that you’re...*insert quality that meets your standards*..."

For example:

"I like that you’re so passionate about xyz..."

"I like that you just light up when you’re talking about..."

"I like that you keep surprising me..."

"I like that I didn’t expect that about you..."

The only reason she should feel chosen is because of the contribution she has made, not because of her looks alone.Remember to be a truly high-status guy you’ve got to communicate to her that you have standards beyond her being hot.

I can’t underline enough how important it is for you, and your dating success, to stop chasing and start choosing women. Not only will you focus on having quality interactions that build your self-esteem, but you will also automatically come across as more attractive.

It’s a win-win for your dating life that means you can mitigate your fears of rejection, and present yourself as the attractive man that you are.

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

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