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How to Date a Woman with Trust Issues

How to Date a Woman with Trust Issues

Knowing how to attract beautiful women is one thing — I’ve definitely taught plenty of men how to do that. But knowing how to date a woman with trust issues? That’s when you’ve truly mastered the game.

A woman with trust issues can be unpredictable. She doesn’t react the way you think she will in typical dating situations. You might forget to call her after you get home one night, and the next thing you know, she wants to bail on the relationship. “What‘s going on here?” you may wonder.

To put it bluntly, she’s freaking out. In psychological terms, she’s “triggered,” which means something about the present situation reminded her of a past event that hurt her deeply — so she’s either running away or lashing out to protect herself.



Triggers are automatic. They stem from the subconscious mind and can involve any type of painful event. For example, women with trust issues may have had past relationships with men who lied. They may have had parental figures who were dishonest, disappointing, or abusive. Or they may have experienced some kind of past trauma with friends, family, authority figures, etc.

Regardless, trust issues often start in childhood. They can also be difficult to break out of. But the more you demonstrate you can keep her safe, through your own secure attachment (more on that later) and clear communication, the more she’ll begin to trust that you’ll never hurt her.

To learn how to date a woman with trust issues, you’ll need to remember these four principles. Practice them like your relationship depends on it … because it does.

4 Tips on How to Date a Woman with Trust Issues

1. Never lie to her

Lying to a woman you’re dating can only lead to problems. You might be tempted to gloss over the truth to avoid conflict once in a while, but that would be a mistake. Even telling white lies like “you look beautiful” when she’s not wearing makeup and has sweats on, can be disastrous later on.

Why? Because lies have a way of being discovered. If she ever catches you in even a simple fib, it’s lights out for your connection.

“Well I’ll just make sure I don’t get caught,” you might think. But here’s the thing: Women are intuitive. They can feel when things aren’t right. So even when she seems to believe your lie, she probably senses that something’s up anyway.

Then, once she suspects something is fishy, she’ll start investigating. You know the drill. She might start asking random questions designed to get info from you. Or she might even go through your phone. (Knowing how to date a woman with trust issues really comes down to four words: Change that phone password! Just kidding. Kind of.)

A woman with trust issues won’t give you a second chance. So you need to be honest with her, even if you know she won’t like what you have to say. Keeping it to yourself will only backfire. If it’s bad, just remember to say it with kindness.

Finally, if nothing else, don’t lie about major things. This includes being in love when you’re not, having a kid, a drug habit, etc.

Will she judge you unfairly once you tell her the truth? Maybe. But lying would be worse. Not only will you trigger her past trauma, but she would have already invested all her time and effort into the lie. It’s almost impossible to undo all that later once she finds out the truth.

2. Communicate a lot

Communication is the key to success with a woman with trust issues. You want to be super clear about logistical events and activities, your expectations, and your feelings.



When it comes to logistical things: Be honest when you need a guy’s night, to hang out with your coworkers, or even just a night “off.” You don’t have to go into detail about what you’ll be doing without her, but make sure to communicate why it’s important to you.

Giving her a heads up in these situations helps her better understand how you like to live your life. If you don’t do this, she may get upset when she can’t get ahold of you and go straight to “he’s cheating” in her mind.

Also, be sure to communicate your expectations early on. If you’re interested in her as a booty call and nothing more, find a way to let her know. Hiding your expectations from her can lead her to believe you want a long-term relationship, which can cause problems down the road if it turns out you’re not on the same page. The same is true if you want to be exclusive with her. Make sure she knows your expectations and that she feels safe to communicate hers.

Lastly, communicate your feelings. This includes good and bad feelings. For instance, if she says something that disappoints you, express your disappointment. This helps her trust that you won’t hide anything from her.

Obviously, it can be tough: Men are often taught not to express their emotions. But she can’t read your mind. Practice authentic communication as much as possible, even at the risk of oversharing. Any woman with trust issues will thank you for it.

3. Learn about what triggers her

We talked about triggers at the start of this article — those little things that can make a person upset seemingly over nothing. This happens because the person who is upset gets reminded of a past trauma, even if they don’t realize it.

A woman with trust issues will often get triggered. And so will you. So, you’ll need to communicate with each other about your triggers so you can prepare for them. When it comes to her triggers, you want to know:

When does it happen?

What types of situations tend to set her off? Maybe she gets super angry when she sees you chatting with female friends, can’t accept when you need time alone, or gives you the silent treatment after you tease her about finishing all the french fries. Really, it can be anything. Take notice of when her triggers happen. Do you notice any patterns?

Why does it happen?

Once you know when she tends to get triggered, ask her why. Do this with sensitivity and genuine curiosity. Could it be related to something in the past? When approached the right way, she will likely open up and tell you.

How does she want you to acknowledge the trigger?

You also want to get clear on how she’d like you to acknowledge the trigger when it shows up. Some women may want you to point it out verbally, while others may prefer you just keep it in mind as you interact with each other.

How to talk about triggers: An example

Here’s one common scenario: Perhaps she feels triggered because you’re still friends with your ex. Taking time to communicate directly about this with her will help you to resolve any tension that may exist.

Find out how she feels about the situation. Why does it trigger her that you’re still friends? When does she feel most triggered? Are there ways to eliminate the triggers without compromising your friendship with your ex? How would she like you to acknowledge the trigger when it shows up?



4. Demonstrate a secure attachment style

Knowing a little bit about attachment theory can go a long when it comes to helping a woman with trust issues feel safe with you. Have no idea what I’m talking about? Here’s a quick rundown.

A quick summary of attachment styles

According to attachment theory, you developed your style of relating to other people when you were an infant. Depending on how your parents responded to you as a baby, you learned that you needed to act in certain ways to keep their attention, get fed, etc.

Attachment theory says that the behaviors you learned in order to get attention from your parents didn’t go away after childhood. You continued them in your adult relationships. These behaviors became your “attachment style.”

There are three basic attachment styles: secure, anxious, and avoidant.

Those who had parents that cared for them reliably developed a secure attachment style as adults. They don’t normally have trust issues and are good at maintaining intimacy with others.

People whose parents tended to their needs inconsistently developed an anxious attachment style. Because they didn’t know when their parents would respond to them, they learned they had to constantly cling to someone to get their needs met. As adults, they often don’t deal with separation well and may have jealousy issues.

Those with parents who neglected (or worse, abused) them developed an avoidant attachment style. Their parents did not meet their needs, so they learned to ignore their needs. Adult avoidants tend to be cut off from their own feelings and therefore find it easier to walk away from others. Being intimate and vulnerable with others often scares them.

Why attachment styles matter when dating a woman with trust issues

Chances are, a woman with trust issues is going to have an “insecure” attachment style, meaning anxious or avoidant.  This actually isn’t uncommon (being about 40% of the population according to researchers). Being able to navigate through a difficult moment with her depends on your ability to demonstrate a secure attachment when she gets triggered.

I know this isn’t easy. After all, it’s easy to let her trigger then trigger you back. You might be a pretty even-keeled dude but when a woman totally clams up, you might feel tempted to blow up her phone. Or maybe her jealous rages make you want to walk out and never come back.

“Hurt people hurt people,” as the saying goes. But if you want to date a woman with trust issues, you need to be the bigger person and respond from a secure place.

To do this, address the issue head-on when she’s triggered. Don’t run away, avoid, or get upset back. Instead, try and get curious about what’s happening for her internally.



If you don’t get the response you want at first, try not to take her reaction personally. It’s not about you. If you get upset, think about what you need to do to calm down so you can communicate clearly and rationally. You might want to take a walk around the block or call a friend first. Just explain that you’d like to address this situation head-on, like a grown-up, and that you just need a few moments to collect yourself.

Later, ask questions to help reveal her state of mind — i.e., what’s happening for her internally. Find out why she’s feeling that way. What is coming up for her? What does she need from you?

Demonstrating a secure attachment helps her to feel safe. She’ll realize that you’re not going anywhere just because she gets triggered and that you can likely make it through anything… as long as you’re communicating.

How to Date a Woman with Trust Issues: Wrap-Up

As I’m sure you’ve figured out in your dating life, human relationships are complicated. Nobody’s perfect. We all have issues. And when we try to partner with someone else, that’s when the “fun” begins, isn’t it?

In all seriousness, trust issues are common. So, knowing how to date a woman with trust issues is important. No doubt, it won’t be a walk in the park — but if you can learn to connect with someone despite their emotional wounds, you will open yourself up to many more potential partners. Who knows? One of them may even become the love of your life.

That’s because part of dating successfully is not just finding the right person. It’s becoming the right person for someone else. So if you’ve met a woman with trust issues and aren’t sure if you want to move forward, I encourage you to practice the four principles I outlined above. Even if it doesn’t work out, you’ll learn amazing things in the process.

And don’t forget: I can help you with that process. Contact me for an intro coaching call and we can figure out how to best move you along your journey. Individual, private coaching sessions — my 3-month Signature program, and my DateHack group coaching program can all give you the confidence you need to transform your dating experience.

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