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how to date an overthinker

How To Date An Overthinker, The Right Way

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If you’ve been wondering how to date an overthinker successfully, this post is definitely for you.

This post is for men or women. 

If you’ve recently met an attractive person who seems to have a tendency to overthink things—then you may be asking yourself a number of different questions:

“Is overthinking, in and of itself, a red flag? Should I avoid dating an overthinker? Or, is it possible that you can actually have a productive, positive, healthy relationship with this type of person?

As someone who’s spent a great deal of my life living as a chronic overthinker myself, I have a unique perspective on this topic. 

I’ve also dated plenty of overthinkers—and this has given me some insight into what to look for, what to do, and what not to do. 

As you probably know if you spend much time reading my blog—I am a firm believer in the alpha mentality. 

I believe that we should live intentionally and be proactive in creating the destinies we desire for ourselves. 

And whenever you choose a romantic partner, it’s vitally important that you choose someone who’s going to be an actual complement to your life—someone who’s going to walk alongside you, make you a better person, and contribute to your overall life success—as opposed to someone who’s going to drag you down, hold you back, or otherwise stifle your growth. 

As Jim Rohn says… “You’re the average of the five people you spend the most time with.”

But I’ve also discovered, over the course of my life, that who you choose to allow into the intimate places of your life as a sexual, relational, and/or domestic partner has an even more profound effect on how successful you become (and how well you perform) than most of the relationships in your life. 

As I tend to say pretty often—if your relationship/dating life is out of whack, that’s going to throw everything else out of whack as well. 

So let’s dive into it and get right to the important stuff—how to date an overthinker successfully, and when to know when it may be time to walk away.

Is The ‘Overthinking’ A Deal Breaker?

This is the first question to ask. 

And to be honest, the answer isn’t always so clear-cut.

To learn more about what over-thinking is, by definition and as a mental process, check out this post by

Here’s how they define it:

“Overthinking — also referred to as rumination — is when you repetitively dwell on the same thought or situation over and over to the point it gets in the way of your life. Overthinking usually falls into two categories: ruminating about the past or worrying about the future.”

Some people tend to overthink, but utilize this natural thought-pattern process in a positive way. 

But for other people, it can actually spiral into negativity. 

And this is really the thing you want to watch out for.

Dating someone who allows their overthinking to cause negative spirals in their behavior patterns is most definitely something that falls under the category of a red flag behavior. 

However, there’s also a gifted and potentially positive side to chronic overthinkers as well. 

Sometimes, overthinkers can be the best at planning things, the most thoughtful, and the most introspective people you’ll ever meet. 

And relationships with them can be incredibly rewarding. 

So let’s talk for a minute about how to know if the overthinker you’re attracted to may be a red flag or a green flag option for dating long term. 

When Is Overthinking A Dating Deal Breaker?

Here are some examples of situations, trends, or behavior patterns that may show you that a particular overthinker is exhibiting red flag dating behaviors: 

  • They allow their overthinking to make them paranoid.
  • Their overthinking results in them having trust issues. 
  • They create imagined scenarios in their head and let their emotions run wild with those scenarios. 
  • They get so exhausted from their overthinking that they lash out at you emotionally.
  • Their overthinking tends to ‘seize them up’ in life—and they struggle to gain any forward progress or momentum with their life goals as a result.  

These are all examples of people who are basically allowing their capacity for deep and complex thinking to impact their daily behavior patterns in a negative way

These are the types of people you probably don’t want to date long-term.

When Is Overthinking A Dating Green Flag?

Here are some examples of behavior patterns that show you that this attractive overthinker may actually be a fantastic potential dating partner: 

  • They stop their overthinking before it causes a negative spiral. 
  • They use their deep thinking capabilities to explore deeper connection and desire with you.
  • They use their ‘overthinking talents’ to plan ahead and live rationally and wisely. 
  • They make orderly plans and stick to them with consistency.
  • They utilize their deep thinking tendencies to develop a habit for introspection, and as a tool for positive self-betterment.
  • They embrace their gift for complex thinking and use it to help them achieve their goals in life. 

People who display these types of tendencies should most definitely be viewed as potential relationship material. 

These are fantastic qualities that anyone would be fortunate to find in their partner.

So if you find an ‘overthinker’ who has matured to this level emotionally—consider it a green light attribute, and feel free to explore the relationship further. 

Is It Hard To Date An Overthinker?

dating an overthinker quote joshua sigafus

It can be difficult to date an overthinker if you’re a person who lacks confidence.

Here’s the thing:

Overthinkers really mentally challenge themselves and their own mental perceptions of the world—and they allow themselves to think deeply about a wide variety of things. 

And they often follow all of those different lines of thought to explore different possibilities.

This is a very introspective process. 

And sometimes, they may want to discuss those possibilities with you.

But here’s the issue that can sometimes arise.

If you’re not a deep thinker or an overthinker, this may feel overwhelming to you. 

And sometimes, it could even lead to you feeling attacked—even if that was never the intent.

It’s important to understand that every over-thinker probably needs to explore all of these deep introspective thoughts and possibilities with themselves. 

This is probably just how their brain tends to operate, and odds are good that this will never change. 

But they’re also going to want to explore these things with you if you are their partner. 

If you can’t handle that kind of thing, just purely as a result of being someone who doesn’t really think deeply about things or talk deeply about things—then dating an overthinker probably isn’t for you. 

Of course, people who allow their overthinking tendencies to delve into negative territory or negative spiraling behavior patterns are definitely not easy to date. These types of people aren’t usually ready for a real relationship—or to be a positive, complementary partner to the other person. 

The reason for this is pretty obvious. 

Whenever we date, we want to make sure to choose a partner who’s ready and willing to be a complement to our life—who’s going to help us make our life better. 

And in turn, we should be willing and able to do the same for them. 

But when you have someone who tends to spiral downward in chaos as a result of overthinking about things—well, that’s just a sign that they haven’t done the kind of introspective work they need to do to become a fully actualized, mature, alpha-minded version of themselves.

How Do You Deal With An Overthinker In A Relationship?

when you choose to love someone quote

The most important thing to remember when you’re dating an overthinker is to be very straightforward, honest, and unassuming when communicating with them.

Overthinkers definitely don’t respond well to beta mindset, negative communication/behavior traits (like passive aggression, gaslighting, etc.), and they don’t do well with people who tend to shy away from conflict.

If you’ve met an overthinker that you’re thinking of dating, and you’ve come to find that they actually display a lot of positive, alpha-mentality personality traits, then you’ll want to deal with them in a very upfront, no-nonsense manner. 

Be open, honest, and ready to talk about whatever issues come up—and don’t shy away from conflict. 

Treat this person with kindness and respect, and allow them to use their overthinking tendencies to help you create solutions together within the relationship. 

This is the best way to deal with an overthinker if you actually want to succeed and have a shot at a positive, fulfilling, romantic relationship. 

What Kind Of Partner Does An Overthinker Need?

vet partners wisely joshua sigafus quote

The answer to this question is pretty simple.

An overthinker needs someone who’s going to shoot straight and communicate directly—who’s going to be straightforward, face problems head-on, and willingly engage in the process of talking about a range of different possibilities together without feeling threatened or letting their insecurities get in the way.

In other words, don’t be on some beta bullshit

If you’ve actually embraced the alpha mentality, and you truly live like it, then dating an alpha-minded overthinker shouldn’t ever be a problem for you.

(Not sure if you’ve embraced the alpha mentality? Check out my alpha mentality code, the Oath of Kings and Queens, here.)

Then, you can appreciate this person’s incredible introspective gifts without allowing those gifts to threaten you or undermine your confidence.

This is how a true alpha dates in overthinker.

What Should You Not Say To An Overthinker?

As a general rule, you never want to treat an overthinker with unkindness or with a lack of respect. 

Never use passive aggression with an overthinker—and always speak up if you have some kind of an issue. 

In other words—you should treat any overthinker exactly as you would treat anyone else. 

As alpha-minded men and women, we should always strive to treat others with the decency and respect they deserve. 

Remember—if this person is worth investing in, it’s worth it to do it right. If they’re not worth it—then you have a responsibility to walk away and to cease engaging with them. 

It’s also really important not to be unappreciative of their capacity to dive deeply into thought patterns and possibilities, and not to undermine their interest in exploring and discussing these ideas and thoughts. 

If you’re dating an overthinker, they may want to talk about things that are bothering them—and they may wish for you to give them reassurance. 

This is part of the process—and as long as they’re not trying to legitimately attack you or allow themselves to negatively spiral, this is something that you should want to help them with. 

If this process bothers you, then don’t date an overthinker. There’s no shame in not wanting to date someone who needs reassurance. Just don’t act like a beta and date an overthinker while also refusing to do the types of things they need to thrive within the relationship. 

If you brush off an overthinker for their complex and wonderful array of ideas, simply because you don’t see the point in those ideas, you’re bound to lose their respect. 

And as a result, their desire for you will slowly die as well. 

This is one of the fastest ways to ruin a potentially rewarding and wonderful relationship with an alpha-minded overthinker.

Final Thoughts

The world is full of different types of people. 

Some of them don’t tend to think very deeply about things, and some of them do.

As always, whenever you’re choosing a partner, the same rules apply. 

Find someone who you work well with, who you mesh well with, who’s an awesome complement to your own personality and temperament, whose presence in your life truly makes you a better person. 

But more than anything, it’s important to educate yourself about how to be a great partner first.

Most people don’t prepare themselves correctly for relationships. 

They don’t embrace the alpha mentality and strive to be the best version of themselves possible. 

You must constantly be striving to:

  • Mind your business
  • Get your money
  • Pursue your purpose in life…
  • And level up mind, body, and spirit

We must also strive, every day, to leave behind the victim mentality—and commit to being radically self-responsible. 

This is non-negotiable. 

If we fail to embrace the alpha mentality, and continue to just react to the chaos of life without taking control of our own destinies—well, we’re going to end up destroying any relationships we try to engage in. 

If you can get this part figured out first, you’re going to have a much better chance of actually making your dating relationships work, regardless of who you choose to date. 

Alright… that’s it for this one. 

Go with grace my friends, and never give up your power. 

Until next time…

Joshua K. Sigafus