The Story of a Reformed Nice Guy and How I Transformed Him Into a Casanova

As you all know, I have my very own long-awaited nice guy Zoom group coaching program coming up next month and I wanted to give you a candid glimpse on what to expect should you decide to hop onboard and get out of the nice guy friendzone with women once and for all.

I often speak of my star client, Owen, whom I worked with back in February. His results in working with me have been no less than spectacular and impressive as you'll see in the following interview below.

And I've since discovered that the bulk of my work with men in this sphere is comprised mostly of those who keep running into the exact same nice guy issues and patterns in their dating lives.

Thus I found it essential to create a uniquely tailored program that will help many of you become accustomed to deviating away from being the nice guy completely, and like Owen, go on to become just the type of man you've always wanted to be with women:

Masculine, strong, a leader, smooth, confident, seductive and poised to do better with women than you ever imagined.

Now, for your bird's eye view on how my coaching helped Owen find remarkable success with women....

Q: Please tell us a little about your upbringing/background and how you became a "nice guy"?

A: My upbringing may not be far off from a lot of other guys reading this–I grew up in a household with a very strict and demanding father and a sweet but extremely smothering mother – the stereotypical “helicopter mom."

I was constantly trying to win the attention and approval of my father through academics and athletics, oftentimes not quite reaching his level of approval and trying to placate my mother’s overbearing nature. Looking back, this is exactly what started my transformation into being a “nice guy”— I had to constantly deny my own wants and needs in order to receive acceptance.  

In other words, I was giving and showing “kindness” with the expectation that I would receive love and acceptance in return.  And man, that’s far from being “nice” – it was straight up manipulative and incredibly self-centered, even though I had no idea I was acting that way at the time.  It was simply the only way I knew how to relate to others.

Much of this lasted through my childhood all the way through early adulthood. It had always been a struggle for me to make friends, especially with other guys. Again, I felt the only way I’d fit in and be accepted is if I acted “nice”, and I was very distrustful of other guys who acted assertively, confidently, or whom I considered to be assholes.  

And, of course, it was the same exact way with women—if only I didn’t act like a "shitbag asshole" like I had seen other guys act, I’d win the acceptance and admiration of women. Turns out that wasn’t the case.

Q: What were your relationships and interactions with women like up until you made your stark transformation out of being a nice guy?

A: I guess you could characterize my relationships with women as me being eternally stuck in the dreaded “friendzone.”

I was friends with a lot of women—we’d chat regularly, go out for food and drinks with friends or by ourselves, but never anything beyond that. At the time, I felt that being assertive and expressing my interest in them would be perceived as being awkward, cocky, or arrogant, so I reverted to what I knew best: acting like a “nice guy."

Every single one of them could sense the desperation and phoniness of it, and it didn’t get me very far. This absolutely destroyed my already lacking sense of self-confidence and left me jaded about dating and women in general. “I’m such a nice guy, I’m doing all the right things, it’s not me, it's THEM.” Even when I did have some success, the relationships were all dysfunctional; I dated women who were simply looking for validation and did not treat me with respect I sought and deserved.  

Once again, I reverted to my “nice-guyness” in order to win their respect and admiration and failed miserably every single time.

Q: Can you tell us how being a nice guy impacted your divorce?

A: This could be the subject of its own article since there’s a lot to unpack, but my lack of self-worth and self-respect stemming from being a “nice guy” were the main contributing factors.  

Looking back, it was a relationship that should have ended at the outset, but at the time I felt like I had finally won someone over and I was desperate to keep her love and attention. I mean, finally, my “nice guy” behavior was working, and I finally found someone who appreciated it, right?  

Sadly, that was not the case. I ignored and rationalized a lot of red flag behavior which left me feeling emasculated and disrespected. I found myself constantly apologizing for things even if I knew I wasn’t at fault, out of fear that she’d leave me if I didn’t. I didn’t assert myself or lead in the relationship; I was constantly trying to please her and defer to her wants and needs at the expense of my own.  

Frankly, for my part, I was not the man I should have been. I was passive, unsure of myself, and a poor leader.

Q: When did you finally decide you wanted to seek out coaching and get specialized help in being in this situation with women? What was "the straw that broke the camel's back" so to speak?

A: After jumping back into the dating scene, which had been quite some time for me (almost 10 years!), I found that I had NO idea what I was doing.  

I signed up for some of the dating apps, created profiles, and started matching/connecting and chatting with women in my area. I never had a problem talking with women since my “nice guy” conditioning made it easy for me to strike up conversations, but I still couldn’t get past the fear of how I’d be perceived if I acted assertively or tried making a move.  

I kid you not, I must have gone on a dozen first dates with most of them leading to second dates, but every single one of them fizzled out after that. I think the “straw that broke the camel’s back” was after I was flatly rejected by a girl I thought I had hit it off well with; she was super cute, funny, pretty successful, and overall checked all the right boxes.  

We had gone on two great dates (or so I thought) with a third one planned, but she cancelled at the last minute, saying that she thought I was super nice but was looking for someone more assertive (literally, that’s what she said).  I was crushed by those words. Seriously, what was wrong with me? Why am I getting rejected left and right? I knew that something had to change and that I couldn’t do this by myself.

Q: Why do you feel you wanted to come to me in particular as opposed to many other male dating coaches out there among us?

A: I accidentally stumbled upon you after watching an Instagram story from Alexander Cortes (solid dude, every guy reading this should give him a follow). He was doing a Q&A and gave you a shoutout and tagged you, so out of curiosity I gave you a follow and started scrolling through your Instagram posts, stories, and blog articles.  

What drew me to you was your no-nonsense, matter-of-factness, “tough love” approach to dating and relationships along with your sense of encouragement. Your articles and IG posts gave specific action steps that demystified the back-and-forth of dating and made the process fun.

And most importantly, I could see you truly cared about your followers and wanted to see them succeed.  Yeah, there are a lot of male coaches out there, but nearly all of ones I’ve seen have nothing to offer other than whiny, crybaby nonsense or the cheesy pickup artistry that’s been around awhile. I don’t have the patience for that loser mentality. You show guys and girls how to win—and how to turn that win into a meaningful relationship.

Q: Please tell us about the most uncomfortable aspects of your transformation out of being a nice guy.

A: The biggest mental hurdle for me was recognizing and coming to terms with my nice guy patterns and how they were hurting me.  

All this time I thought I was doing the right thing by acting nice, being overly accommodating and generous, when in fact these behaviors were manipulative—I was giving in order to receive. I had to deprogram myself to NOT do that, and that led me to feel selfish or coming off too strong when I attempted to assert myself.

During our time working together, I remember constantly asking you (Jenny) “is it okay if I do X? Will I come off as an asshole if I do/say that?” And you were right there to assure and guide me so that I was indeed doing/saying the right things.

“What is your gut telling you?” I remember you asking. And over time, your guidance helped build the confidence I needed to get over those mental hurdles and simply put myself out there—to shoot my shot and be fearless in doing it. It was really when I started to get a few “wins” with your guidance that I knew I was onto something.

Q: What did you learn most about women in this process?

A: Many things, but the biggest takeaway is that women LOVE assertiveness. It projects unshakable confidence and self-assuredness, self-respect, and lets them know, “Hey, I ain’t here to bullshit.”  

Jenny has talked about this before, but it really brings out sexual polarity—guys need to be the rock and the leader in the relationship, the protector and the provider; women need to lean on them, trust them, and follow their lead. Project any modicum of insecurity or uncertainty, and you’ve just sh*t the bed with your chances with any high-value woman.  

Stop pedestalizing women, stop worrying about what women may think or say if you do XYZ, stop worry about outcomes, PERIOD—just be effin’ bold and have fun with it. If you’re not having fun and enjoying yourself, you’re doing it all wrong and need to reevaluate your actions and intentions.

Q: What did you learn most about yourself and your masculinity?

A: I feel like I’ve unlocked this whole side of me that I never really knew I had but was always there. I learned that I truly love being the new “bold guy," taking the lead, being unafraid to assert myself, and willing to walk away if I’m not being treated with the respect that all good high-quality men deserve.

It comes naturally to me now and I feel like I radiate it. And there’s been a ripple effect in other areas of my life: my work relationships have improved and I’m performing better, dynamics between myself and family members have also improved, and people are generally more drawn to me. Gone are the days where I had to put on a show to make people like me. Now, I simply accept and love who I am, don’t give a sh*t about what others may think (women included). It’s liberating and I love it.

Q: You've mentioned to me that "the nice guy is always going to ever-present" a bit like a recovering alcoholic who will always have strong sentiments about drinking. Can you explain that more in-depth and what you do personally to stay on top?

A: Like you said, even though I’ve ditched the “Nice Guy Owen” persona, he still tries to pop his head up every now and then. Usually this happens during times of stress, or whenever moments of self-doubt begin to creep in, or anytime I’m feeling down in general.  

It’s in those moments when I’m looking for a quick hit of external validation to feel better, and boom, there’s Nice Guy Owen, waving his hands and ready to come back to start his validation-seeking bullshit all over again.  

For anyone that’s trying to kick the nice guy habit, it’s a conscious effort to recognize those old patterns and prevent them from reoccurring. There will be times when you’ll slip up—and that’s okay—just cut yourself some slack, recognize what you’re doing, and stop the behavior, whatever that may be.

For me personally, if I find myself slipping back into old habits, I do the OPPOSITE of whatever I was doing. Was I people-pleasing? I knock that sh*t off. Over-explaining myself?  Nah, I don’t owe anyone an explanation. Being over-accommodating? I immediately stop and take care of my needs first. Feeling obligated to do something because I might come off as “not nice” if I don’t? Then I simply don’t do it.

Like I said, it really is a conscious effort to pick out those bad habits and put a stop to them. You won’t always catch yourself doing it every single time, but it’ll become a lot easier with practice.  Having that self-awareness is key.

Q: Tell us a little about the very high quality woman you're currently in a serious relationship with since you worked with me. She fell for you HARD and said she loved you first. Can you explain the remarkable change in you and how it had an impact on her feminine behavior towards you?

A: Boy, Jenny, I’m still flying high from it all! So, I met my woman, Alexa, a few months ago after some chit-chat over one of the dating apps. She’s a doctor who had just turned 30, and based on our conversations I knew I wasn’t dealing with another run-of-the-mill “pick-me” woman who was just trying to accumulate another satellite simp to boost her already low self-esteem.  

She was funny, ridiculously witty, bloody smart, kind-hearted, and stunningly beautiful. You and I were still working together at that point, and you had written up a personalized “Action Plan” for me to implement on dates, much of which you can find in this article, and I committed myself to doing every single one of the bullet points you wrote up for me.  

Long story short, not only did your action plan work spectacularly—almost freakishly on point—everything just seemed to “click”. The chemistry was there, the conversation flowed, we were flirting HARD, I asserted myself exactly the way you told me to, and she was floored by it.  

I was literally watching her initially somewhat-guarded demeanor melt before my eyes as I followed your action plan, and she was falling right into that feminine behavior that you’ve talked about numerous times. I found myself even more embolden by it—here’s someone that finally appreciates the masculinity in me!

And again, it just flowed naturally; I didn’t have to think about “being masculine”—it just happened, and I loved it.  As we were walking out of the restaurant, she grabbed my hand before I was able to make a move, and I knew right then I had a winner.

Fast forward to today, we’re in a committed serious relationship, and we’ve been talking about future plans together—including marriage.  It almost hard to describe the change that’s occurred since rediscovering my masculinity and how it’s impacted my life. Everything seems “brighter.”  

And I don’t have anxiety about the future and what it may bring, and I can see this reflected in Alexa—she’s trusting of me, follows my lead, and feels “safe” with me (she’s said this on several occasions). It’s like a positive feedback loop: my masculinity and her femininity bring out the best in each other. It’s one of the best feelings I’ve ever had.

Q: What would you advise men today who will be reading this about being a nice guy? What's the most important piece of advice you would give them?

A: First and foremost, you gotta do the internal work first.  If you’re approaching dating and relationships from a position of low self-worth and neediness, it’s going to be painfully obvious and it’s only going to feed the negative narrative you tell about yourself.  

Seek help and read books like “No More Mr. Nice Guy” by Dr. Robert Glover, talk to a therapist (I have and still do), reach out to Jenny and participate in her Nice Guys coaching program and just do the work.

Next, STOP WORRYING ABOUT ALL THE WHAT-IFS.  Getting so hung up on what might happen if you do or say X to a woman you’re interested in is exactly what’s paralyzing you and projecting insecurity whether you realize it or not. Assert yourself. Speak up. Take action. And stop worrying so much about the outcomes—these aren’t life-and-death situations after all.  Have confidence in yourself and take charge.

Finally, have fun with it. If you find yourself stressed out with the dating scene, then something is very off, and I can almost guarantee you that you’re acting like a “nice guy.”

Take a step back, evaluate why you’re doing/saying the things you are, and adjust.  If you’re unsure what to do or how to correct those behaviors, talk to Jenny.  It’s one of the best things I’ve ever done for myself.  And I’ve already invited Jenny to my future wedding with Alexa (lol).

Also, it’s important to understand the difference between a nice guy and a good guy:

A nice guy is manipulative. He gives in order to receive. It can happen between virtually anyone in your social circle—friends, colleagues, family members. You’re over-accommodating and giving because you know you lack something and it comes from crippling insecurity. And a complete lack of confidence. And it comes off as slimy aka used car salesman.

A good guy is the guy who willingly gives and doesn’t expect people give to him in return. He has a solid sense of boundaries—he knows when he’s being taken advantage of and isn’t afraid to call out bad behavior when he’s confronted with it (hence the asshole).

The good guy gives from a place of self-respect and confidence. It comes down to knowing that it’s meaningful, generous and thoughtful. He also understands what the other people value and it makes what you do more authentic.

There you have it. Amazing and inspiring transformation out of being the nice guy.

If you are interested in our upcoming Zoom nice guy coaching program, please email me at:

lovepilled@protonmail.com

And surprise, Owen himself will be my featured guest speaker who will be expanding more intimately on his own personal transformation and will also be available to answer questions.

If Owen can do it, you certainly can too. Believe it.

Love and Many Blessings,

Jenny

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