Episode 106

The Myth of ‘Good on Paper’ – Why Your Checklist is Keeping You Single

Your “perfect man” checklist might be the very thing keeping you single.
17 mins
Hilary Silver dressed in a black t-shirt with the word 'AMOUR' and leather pants poses playfully, blowing a kiss against a simple background.

Show Notes

Your “perfect man” checklist might be the very thing keeping you single.

You made the list because you were told that’s how smart women date. Know what you want. Don’t settle. Have standards. And yet you keep ending up with men who look great on paper and feel wrong in real life. Or you eliminate every man before he ever has a real chance. At some point you have to ask yourself if the list is actually serving you.

In this episode, Hilary breaks down three reasons the checklist backfires. She explains the difference between surface-level criteria and real character, why most women struggle to recognize emotional health when they see it, and how “high standards” can quietly function as protection from vulnerability. Shared religion, impressive credentials, and lifestyle alignment may check boxes, but they do not guarantee integrity, kindness, or emotional maturity.

This conversation is not about lowering your standards. It is about refining them. It is about learning to assess consistent behavior over optics, trusting what you feel in your body, and choosing from discernment instead of fear. When you stop dating from a spreadsheet and start dating from self-trust, everything changes.

In this episode, you’ll learn...

Episode Highlights:
  • Why your checklist might be screening for credentials instead of character
  • The difference between logistics that matter and boxes that mean nothing
  • How men can “perform” emotional availability and how to tell when it’s real
  • The subtle way high-achieving women turn dates into auditions
  • When “high standards” are actually fear of vulnerability in disguise
Episode Breakdown:
[00:00] The Problem with the Partner List
[03:12] Surface-Level Traits vs. Real Character in Dating
[05:53] How to Spot Real Emotional Availability
[08:45] The Dangers of Assumptions in Relationships
[12:01] Are Your High Standards Blocking Love?
[14:45] How to Use a Dating Checklist the Right Way

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Let’s talk about the list.

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You know you have one all the criteria of

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what you want in a partner.

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Having this list means you know

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what you want and you won’t settle.

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You have standards and you’re proud of it, except

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that somehow having that list hasn’t really served you

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because here you are still single, either staying

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with the wrong men despite the list, or eliminating all men

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because of the list.

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So today we are talking all about the list.

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’cause what good is it if it’s not really helping?

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I know you’ve been told to make a list of the qualities

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and traits that you are looking for in a partner.

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It’s age old advice,

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and in theory it sounds like a great idea.

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It’s like having a grocery list

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before you go shopping so you don’t forget anything

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that you need or want at the store.

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So you’re man shopping and you have your list.

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It keeps you honest and on track, not overlooking things

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or forgetting things that are important to you.

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That’s all fine and good.

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It feels empowering,

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like you’re taking control of your love life.

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You’re being intentional about your next partner,

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except here’s what’s actually happening.

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Your list isn’t protecting you.

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It’s probably sabotaging you

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because despite the list, you keep ending up with men

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who don’t measure up making concessions or settling

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or it’s been three years or five years or longer,

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and you’re still all alone not getting

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what you want in a partner or in a relationship.

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So here are three reasons why the list has become part

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of the problem and the micro adjustments

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that will help make a big impact.

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First, you’re checking surface level boxes

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and completely missing what actually matters.

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Here’s what I mean by that.

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It’s that you’re not making a distinction between

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what I call gatekeeping criteria versus character criteria.

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Gatekeeping criteria are the basic logistics that have

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to work before you even go on a date.

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Does he live close enough

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that we can actually date each other?

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I don’t believe in LDRs long distance relationships.

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Is he at a compatible life stage?

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If you’re 60 with grown kids, you

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probably don’t want someone who had kids later in life

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and still has toddlers.

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Are there major lifestyle deal breakers?

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You’re retired and ready to travel the world.

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He’s building a brick and mortar business

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and won’t be free for a nomad life for many years to come.

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These are just examples of gatekeeping criteria.

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These are legitimate filters.

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They’re practical and they’re quick decisions.

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If he lives three states away

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or has five kids under 10, when you’re done with that stage

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of life, you just don’t go on a date with this person.

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It’s very simple. But here’s where women get into trouble.

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When those basic boxes are checked,

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they think they found someone promising

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and they get excited about the potential.

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Wow. Finally, a man with a high level job

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who has older kids like me, he’s tall, successful, went

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to a good school and shares my religion.

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This could really be something.

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And now they’re invested in the idea of him

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before they’ve actually evaluated who he is.

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They’ve checked the surface level boxes

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and this feel like evidence that this is going somewhere.

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So they overlook red flags.

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They excuse behaviors they wouldn’t tolerate otherwise,

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and they stay longer than they should

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because on paper he’s everything I wanted.

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But all of those surface level criteria tell you absolutely

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nothing about who he is as a person.

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His character, yes, he has a high level job,

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but does he have integrity?

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Yes, he’s educated, but is he kind?

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Yes, he’s the right height. Is he emotionally available?

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Yes, he goes to your church.

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Does he take responsibility for his actions?

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You need to be looking for values based criteria,

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character traits, who he actually is.

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And here’s the thing about values versus

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interests or circumstances.

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People’s interests change over time.

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Their circumstances change, but their values rarely do.

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You both might love hiking right now,

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but in five years, one

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of you gets injured or loses interest.

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That’s not a deal breaker.

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If you share core values,

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you might both have demanding careers right now,

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but careers shift priorities change and life happens.

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What matters is do you both value integrity, respect,

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partnership and communication?

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Those things don’t change.

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A man who takes responsibility today will take

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responsibility in five years.

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A man who’s kind to waiters now will be kind

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to waiters in 10 years.

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A man who is generous now will more than likely

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continue to be generous.

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That is what you should be evaluating.

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Not whether he checks boxes on height, income, education,

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and hobbies, but most women spend way more time excited

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about the surface level stuff than they do actually

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assessing character

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and then ending up in relationships with the wrong men

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and staying too long trying to make it work.

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So you’re checking these somewhat arbitrary boxes on your

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list and making decisions about him

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and your potential based on credentials

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instead of character.

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The second reason, even if you have the right things on your

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list, quality

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and values-based criteria like emotional

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availability, kindness, integrity.

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That doesn’t mean that you can actually recognize

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what those things look like in real life,

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or more importantly, recognize when someone is faking it.

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Most women say they want an emotionally available man,

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great, that’s on the list.

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But what does that actually mean?

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What does that look like in real life when he’s standing

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right in front of you?

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Is it sharing a personal story about your

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childhood on the second date?

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Is it saying, I’ve done a lot of therapy

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or using words like emotional regulation

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and attachment style?

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Is it crying at a movie

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or telling you he’s in touch with his feelings?

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Maybe, but maybe not.

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Just because you have emotionally available written on your

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list doesn’t mean you can tell the difference

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between a man who’s genuinely open

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and vulnerable versus a man who’s learned the language

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and is using it to hook you in.

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A man who knows he’s supposed to act a certain way,

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can do it once or a few times or for a short period of time,

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but if it’s not real, it’s not consistent

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and it’s not sustainable, he can’t keep it up

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because it’s just not genuine for him.

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And when you’re busy checking the box on your list,

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because yes, he’s gone to therapy

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and he is worked on himself, you don’t learn

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to feel it in your body.

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You’re not in your own senses.

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You’re not actually feeling whether this is real

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or whether it’s a performance.

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Your intuition is a felt sense.

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It’s telling you and alerting you when something is off,

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but you can’t access your intuition when you’re in your

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head, busy checking boxes.

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Your intuition definitely doesn’t care about

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a list on paper.

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Knowing and feeling the difference is discernment.

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The ability to feel when something is off,

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even if you can’t articulate why.

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It’s the ability to recognize when someone is performing

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versus when they’re being real.

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The ability to trust your gut over a checked box.

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This discernment happens in your body,

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the tightness in your chest when he says something

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that sounds good but feels wrong.

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It’s the sense of ease

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and safety that you feel

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with someone who’s genuinely present and healthy.

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It’s noticing that you’re performing

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and on guard instead of relaxed and just being yourself.

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It’s your nervous system telling you, yes, this is right,

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or no, something is off here.

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So you can have the perfect list every single thing on.

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It could be a legitimate character trait or a value,

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but if you don’t know what a true expression of

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that trait looks like, how to feel the difference

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between real and fake, the list is worse than useless.

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It’s dangerous because it’s giving you a

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false sense of security.

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And now I’m going to flip this for a second

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because it’s not just you doing this to him.

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Women get way more caught up in the list on

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paper than men do.

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Men don’t evaluate a potential partner based on her job,

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her life stage, or her income, the same way

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that women evaluate men.

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So what I see all the time, especially

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with high achieving women, is that all the focus

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for her goes into being on that list of checked boxes.

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She has the great career and lifestyle.

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She’s fit and good looking. She takes care of herself.

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She has the achievements and the credentials,

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and then she will show up on dates as if she’s auditioning

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for a part or interviewing for a job emotionally detached,

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unavailable, not being authentic, real or vulnerable.

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It’s performing. So you want to check his boxes

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rather than just being yourself

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and then letting the chips fall where they may.

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You can’t create intimacy, chemistry

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and real connection from a place

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of evaluation and performance.

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You have to actually be present, be yourself,

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be a vulnerable enough to let someone see you

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and curious enough to actually see them.

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But the checklist keeps you trapped in your head on both

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sides of the equation.

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You’re evaluating him, you’re performing for him,

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and then neither one of you is actually there.

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And one more very important thing

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before we get to the final reason

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that the list is doing you wrong, I need

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to call out one specific box

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that perfectly illustrates this whole problem.

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Religion. This is one of the most

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dangerous boxes on your list

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because it feels like you’re being discerning

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and having standards

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and making a conscious choice when actually you end up

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making a lot of assumptions.

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If you are religious

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or deeply faithful, doesn’t matter what it is, Christian,

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Jewish, Muslim, spiritual, whatever,

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and you meet someone who shares your faith,

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you’ll make all kinds of judgements about him instantly.

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We are all biased in our own favor in this way.

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You think, oh, good, he’s Christian like me.

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He must be a good man, or he’s Jewish.

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We we definitely share the same values. Or he’s spiritual.

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He must be conscious and evolved.

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Then you actually stop paying attention to who he is.

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Just because he goes

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to your church does not mean he’s a good man.

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Men who go to church also lie, cheat, manipulate,

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have addictions, have narcissistic tendencies

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and can be emotionally abusive just like any other man.

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In fact, and this might make some of you uncomfortable, some

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of the most toxic men that I’ve encountered in 25 years

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of practice hide behind religion.

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They use it as a shield.

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They go to church every Sunday,

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but they treat their partners terribly behind closed doors.

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They quote scripture and they cheat.

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They lead Bible study groups

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and are controlling and manipulative.

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Women have said, oh, I thought, you know,

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he comes from a Jewish or a Muslim family.

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So we’re already aligned in so many things.

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They made so many assumptions about this, this man,

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and he turned out to be a horrible person.

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Women miss all the signs and cues because shared faith

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and religion becomes a checked box

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that makes them feel safe.

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Shared faith is one piece of information.

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It can matter for lifestyle compatibility

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for raising children, shared spiritual values,

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but it does not tell you about his character.

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It does not guarantee he is emotionally healthy,

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that he’s a good person or a good partner,

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and that he will treat you well.

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Being of the same religion

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or faith is just simply that and that alone.

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And when you assume it means more, you are blind

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to everything else he can be,

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and your list becomes dangerous.

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So I hope that you will take that to heart.

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So the last reason, the list keeps you safe from ever having

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to choose anyone.

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It’s sabotage.

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You’re using it to narrow the field so much

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that no one can actually get through.

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Now, you didn’t consciously create it for that purpose.

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You genuinely think that you’re maintaining standards.

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But if we’re really being honest,

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the checklist serves a very important subconscious function.

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It protects you from having to be vulnerable.

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Think about it. If your list has 12, 15, 20 requirements,

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he must be this tall, make this much money, have this kind

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of degree, live within a radius, have kids this age

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or no kids at all, share your faith, work out regularly,

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have a close relationship

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with his family, but not too close.

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Want kids, but within a specific timeframe

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and be emotionally intelligent and masculine

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and ambitious, but also present.

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You get the idea. No one is going to check every single box.

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No real human being is going to meet all

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of those requirements.

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And that’s the point,

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because if no one ever meets all of your criteria,

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you never have to actually choose anyone.

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You get to stay safe sitting on the bench, opting out.

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You get to keep dating and dating.

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Finding fault with everyone saying, I just can’t find anyone

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that I’m interested in,

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or no one measures up to my standards.

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But the truth is, you’re finding fault on purpose,

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subconsciously on purpose.

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It’s kind of like you’re backing yourself into a corner

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where no one is ever good enough.

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And from that corner, you’re safe and protected.

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You don’t have to risk getting close.

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You don’t have to be vulnerable.

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You don’t have to face the possibility

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of getting hurt again.

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And here’s what you’re really afraid of,

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making the wrong choice again, being disappointed again,

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investing in someone who doesn’t work out, again,

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trusting your judgment

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after being wrong so many times before.

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And underneath all of that is being afraid

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of intimacy itself.

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Getting close to someone means they might see the real you.

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The parts that you think are unlovable,

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the parts you think aren’t perfect.

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Getting close to someone means you might get hurt, rejected,

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abandoned, let down, betrayed.

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Getting close to someone means you have to trust them.

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And trusting feels terrifying when

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you’ve been let down before.

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So you create these obstacles

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and the checklist becomes your excuse

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and your shield, your reason why you can’t find

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anyone, it’s not me.

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It’s just I have high standards and no one meets them.

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I’m not gonna settle. Don’t ask me to settle.

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But what if the real problem is

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that you’re using impossibly high standards to avoid having

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00:14:41.315 –> 00:14:42.935
to actually let someone in.

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This is sophisticated, intelligent, well disguised,

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sabotage, but sabotage nonetheless.

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And the saddest part is that you do actually want love.

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You might be lonely

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and you might genuinely want partnership,

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but underneath that desire is a deeper fear.

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That fear of intimacy and vulnerability and being hurt.

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And as long as that fear is running the show,

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you’ll always find a way to keep everyone out.

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The checklist is just the tool that you are using to do it.

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So the list is still good advice, but there’s a right way

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and a wrong way to use it.

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And it will either help you along or it will hold you back.

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It helps because when you get it right,

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you’ll stop picking the wrong men despite the list.

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Or stop eliminating all men

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because of the list holding you back

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because you’re subconsciously blocking

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00:15:35.395 –> 00:15:36.845
what you really want the most

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because it scares you to open yourself up to the what ifs.

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00:15:40.425 –> 00:15:43.845
You stop eliminating incredible men for superficial reasons.

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00:15:44.265 –> 00:15:48.005
You stop staying too long with men who look good on paper,

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00:15:48.705 –> 00:15:52.325
but feel all wrong and you stop hiding behind requirements

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and start actually choosing.

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You become a woman who trusts herself, who listens

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to herself, who knows what she wants,

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and she can recognize it in person in real life.

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When she sees it standing in front of her,

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you can discern this character.

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You can feel the difference between real and fake.

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And that’s when it gets fun because it’s effortless,

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and this is when it actually will happen for you.

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Thanks for listening.

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Make sure to subscribe to the YouTube channel so

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that you can share your comments on all of our episodes.

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And if this resonated with you

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and you’re ready to develop real discernment

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to stop sabotaging yourself

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and become the woman who knows how

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to choose the right partner, go to ready

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00:16:33.045 –> 00:16:37.285
for love inc.com/apply to learn more about working with us.

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See you next time.

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