12 tips for dating a guy with low self esteem

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If you’re dating a guy with low self-esteem then you’re likely struggling.

You have strong feelings for him, but you can’t prop up his self-esteem and self-worth all on your end.

Here’s what to do if you’re dating a guy who’s pretty down on himself or doesn’t recognize his own value. 

1) Be clear on your role

Dating a guy with low self-esteem is one thing. Being his therapist is something else entirely: and it’s not a relationship, or at least it shouldn’t be. 

You’re not here to fix this guy as if he’s a broken car or computer. 

His problems are ultimately his own. 

Be clear on your role: you’re his partner, but you’re not somebody who should be taking responsibility for his well-being on your shoulders. 

All too often, trying to fix someone becomes a dangerous codependent cycle that drags both of you into an anxious vs. avoidant cycle. 

2) Support, but don’t stifle

Supporting a partner who’s having a hard time is a healthy part of any relationship. 

The problem that occurs is when support becomes a stifling kind of control and almost parental concern. 

A romantic partnership all too often starts to mirror excesses and lacks of love that we experienced in our family situation growing up. 

It’s all too easy to try to support a guy you’re dating but cross the line into almost “mothering” him. 

Without getting too Freudian, this is the last thing you want happening in any romantic relationship, obviously. 

You’ve heard of helicopter parenting, and the only thing that’s as bad in close relationships is a helicopter girlfriend or boyfriend.

3) Speak your mind

You don’t owe anyone sympathy or playing nice, even your boyfriend. 

Far too often, we walk on eggshells when we are in love with someone or have feelings for them. 

We dread hurting their feelings or saying “the wrong thing.”

Fair enough, to an extent, but the issue is that the less you open up about how you really feel the more you will have a shallow and even partly false relationship. 

This will make you very unhappy, to say the least. 

When I was in the situation of dating a girl with quite low self-esteem last year I contacted Relationship Hero, a site where dating coaches help guide you through situations like this. 

I found my coach ultra-helpful and knowledgeable, and he explained to me how I could say what I really thought while still being compassionate. 

To cut a long story short, I saw how my ex-girlfriend was sabotaging herself and learned to start being more honest with her about the patterns I saw instead of holding back. 

Relationship Hero seriously knows their stuff and I recommend checking them out

4) Shift their vision

Many times low self-esteem is deeply rooted in the past and familial or social experiences of exclusion, belittlement, and mistreatment. 

The downside is that this can lead to embracing the victim mentality, which just feeds into a downward spiral. 

The truth is that many times we really are victims, but if we focus on that we end up writing a script in which we have the worst role and seem born to lose. 

The guy you’re dating is not a loser and he likely has a lot of potentials even if he doesn’t yet see it. 

If possible, speak openly with him and try to help him shift his vision.

This isn’t about getting him to say self-help mantras or just watch more Tony Robbins on YouTube (although that certainly won’t hurt!) it’s more about showing him a new way of looking at things. 

5) A different POV 

Helping shift your boyfriend into this new point of view (POV) is not about making him more “positive” per se.

Feelings come and go and they aren’t going to save your relationship.

Instead, as my coach at Relationship Hero advised me, you can focus on showing him action-oriented steps he can take to start turning things around.

Instead of changing his feelings and thoughts, focus on changing what he does. 

If he has low self-esteem about his appearance or body type, encourage him to go to the gym or take classes. 

If he has a feeling that he’s boring or “basic,” encourage him to explore a unique interest he has and point out that he’s not boring. 

These are sort of like hints. It’s up to him to take them and find the man inside, but you can point him in the right direction.

As Bob Dylan sang in his 1970 song “the Man in Me”:

“Storm clouds are raging all around my door

I think to myself I might not take it any more

Takes a woman like your kind

To find the man in me…”

6) Unlock his hidden door

What if I told you that every guy has a hidden door?

I know I do.

Behind that door is the guy who always wanted to be a hero for a woman, to be her guy. 

Behind that door is hope and confidence about being the one and only for a special woman. 

Maybe I’m just a romantic at heart, but the truth is that every man has this desire to be a protector and provider inscribed into his very nature, deep in his DNA. 

Relationship psychologist James Bauer calls it the hero instinct

This isn’t about capes and saving you from a burning building (although you never know!) it’s more about you saying and doing the things that help him feel needed, masculine and competent in a way that triggers his deep commitment. 

A guy who’s lacking in self-esteem often grew up without a father, as in my case. He is seeking his “inner man” so to speak. 

Now, nobody can give or create that for him: only him. 

But you can show him that you see and love his inner man, including in certain ways by sending specific texts and treating him in specific ways. 

I strongly recommend to look into this hero instinct concept and see how it can help you unlock his hidden door. 

Click here to watch the free video.

7) Shut down his self-sabotage

Men with low self-esteem have a nasty habit of self-sabotaging. 

Due to various reasons including childhood trauma or difficulty finding his identity and place in society, he may believe he’s not worthy of you. 

This is a very hard belief to change because what we believe deep down goes beyond the conscious level. 

It’s deep in the bones and often ingrained in really unconscious ways. 

In order to shut down his self-sabotage, the best way is to make a very obvious but very crucial point:

If he weren’t “good enough” for you then you would not be with him. 

Point blank. Simple as that. 

Regardless of how he sees himself, you clearly have feelings for him, so you now turn the tables and point out that if he thinks he’s unworthy of you then he’s basically questioning your judgment. 

He is worthy. He’s the guy you’re dating

8) Encourage proactive activities

Another important one of the top tips for dating a guy with low self-esteem is to encourage proactive activities.

What counts as proactive? 

Basically, anything that expands his circle of experiences and talents. 

Whether that’s cooking, ziplining, learning to fix cars or just hanging out with his friends and watching sports and similar masculine activities, you should encourage it. 

These aspects of group belonging and validation will do him a lot of good and help boost his confidence in the relationship. 

9) Interrupt the victim narrative

The victim narrative is like a drug. The more you indulge in it, the more addictive it gets. 

If you’re dating a guy with low self-esteem, he may be an addict. He may see himself fully in the victim role. 

He’s a victim of life and of love. He’s a victim of tragedy. He’s a victim of not being tall. He’s a victim of having a big forehead, or having his parents divorce, or having a family member die. 

It may all be true. 

But the more he indulges in it, the worse it gets!

That’s why you should interrupt the victim narrative by pointing out to him that while you sympathize, you think he is also a really impressive guy and that he shouldn’t focus only on downsides. 

As newgrass band the Avett Brothers sing in their 2016 song “Victims of Life”:

“You got the victims of violence, victims of peace 

You were all victims, exactly like me 

Victims of anything, and all the above 

Victims of hate, victims of love 

Victims of hate, victims of love.”

10) Call him out on childish behavior

The truth about the victim mentality is that it’s often very childish. 

Many times low self-esteem comes when we are stuck in infantile patterns. 

It’s not that it’s weak or “bad,” it’s just that low self-esteem is so often self-reinforcing. 

I’ve suggested some ways to help break the narrative, but sometimes you do just need to call him out on childish behavior. 

He’s not the only one who’s doubted his worth in life…

He’s not the only one who’s struggled. 

Make sure to emphasize to him that you have his back, but you also believe in his capacity to become more confident and empowered.

11) Help him get out of his head

Many times self-esteem is reinforced by a negative inner voice. 

I’ve had it in the past and I know how it goes:

It replays the same script at you telling you you’re not good enough, you’re cursed or you’re far “different” than others (in a negative sense). 

If you’re dating a guy with low self-esteem then he’s likely got this inner monologue talking his ear off. 

Help him get out of his head:

Suggest cooking together one evening, or go to a new place you’ve never been…

Tell him about an interest or fantasy you’ve never discussed before. 

Help him break out of this stupid monologue that’s got him trapped. It’s really not worth his time, but sometimes the best way to help him realize that is to change his focus. 

A lot of this is really about what I mentioned earlier in triggering his hero instinct.

You can learn exactly what to do by watching this simple and genuine video by James Bauer.

It presents a lot of tips about how to help him access his deeper confidence and see you as his one and only despite some misgivings he has about his own value. 

12) Show him you’re for real

When you’re dating a guy with low self-esteem, he’s holding his breath waiting for you to pull the plug.

Maybe he’s been dumped before multiple times. And you can bet he’s afraid of it again. 

He believes he’s not good enough. 

This is where you show him you’re for real. 

Be patient. Don’t coddle him or be condescending, but show him that you do care and that you do have patience for some of his insecure patterns in the same way that he has patience for yours. 

Helping him find his voice 

Writers often talk about how they “found their voice” at some point in time and their struggle to do so.

Finding the voice is almost a shamanic or mystical process, often involving suffering, confusion and self-doubt. 

Think of your boyfriend in this way: 

A man who is trying to find his voice and speak his truth to the world without fear or shame. 

In this article I’ve emphasized something crucial: 

Supporting a guy you are dating and being his therapist are two entirely different things. 

Your goal is to help him find his voice and realize his potential, but you can’t “fix” him or force him to find his inner strength. 

That’s up to him.

The fact is that he’s ultimately the one who has to find his voice and embrace his inner masculine. 

The best you can do is know how to trigger his hero instinct as this free video from James Bauer explains. 

I recommended this video earlier because the hero instinct is a concept that truly unlocks so many closed doors, especially in an insecure man. 

I believe that who we are is strongly shaped by the situations we’re in. 

Some situations (and people) bring out our best, some bring out our worst, and some bring out nothing at all…

Your job? To know the right actions to take and words to say to bring out his inner hero and make him realize that he’s far higher value than he may have previously thought. 

Here’s a link to his excellent free video again

Can a relationship coach help you too?

If you want specific advice on your situation, it can be very helpful to speak to a relationship coach.

I know this from personal experience…

A few months ago, I reached out to Relationship Hero when I was going through a tough patch in my relationship. After being lost in my thoughts for so long, they gave me a unique insight into the dynamics of my relationship and how to get it back on track.

If you haven’t heard of Relationship Hero before, it’s a site where highly trained relationship coaches help people through complicated and difficult love situations.

In just a few minutes you can connect with a certified relationship coach and get tailor-made advice for your situation.

I was blown away by how kind, empathetic, and genuinely helpful my coach was.

Click here to get $50 off your first session (exclusive offer for Hack Spirit readers).

Paul Brian

I’m a multimedia journalist with experience in print, photography, video, and online. My passion is reporting on individuals, faiths, nations, and situations that impact us all on the journey of life.

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