Throughout my teen years and early twenties, dating was the source of my greatest pain, stress, depression and frustration. I simply didn’t do well with women.

Unbeknownst to me, I suffered from Nice Guy Syndrome, and what appeared to be “bad luck” with women was actually a completely logical pattern of reactions based on how I was behaving socially.

I always knew that I wasn’t repulsively unattractive at least, and girls generally seemed to enjoy my company, so it was a complete mystery why I’d go four years without sex despite desperately trying to date, or why the girlfriends I did have all left me within a few weeks.

In this article, I’m going to share the top 10 reasons why nice guys finish last in dating, and relate to each point with a painful memory from my own mistakes.

Trying to keep her happy

When I secured my first long term relationship, I had a simple goal: keep her feeling happy all the time. I figured that if she always feels “good” around me, the relationship would continue. I mean, why would you want to leave someone who always makes you feel good, right?

You guessed it; she left me! And for another dude who probably wasn’t nearly as nice as I was. What an insult!

What I didn’t understand is that attraction and connections require a full range of emotions, as well as transparency and honesty. 

By trying to make her happy all the time, I limited her emotional experience (i.e. I was boring and overly comfortable to be with), and I had to be fake to achieve this goal and so we lost our connection due to my transparent manipulation.

Avoided rejection

I always assumed that if a girl said No to me that it was somehow accurate criticism about my lack of worth. A rejection would haunt me for weeks, sometimes even for years. I’d spend hours trying to figure out what I should change about myself based on this “feedback”.

Eventually, I came up with a strategy to reduce and prevent rejection: don’t try!

For many years after that first relationship ended, I simply put myself in proximity to women and hoped they’d make a move. I didn’t dare risk initiating or leading an interaction beyond its current level.

This strategy “worked” in that I didn’t get rejected. But it failed in that my overall dating results were the same as someone who always got rejected: almost nothing at all was happening.

By trying to avoid getting a No, I was forced to act as if they had already said No, which caused the same result anyway. I would have done better asking every girl I ever met out on a date!

Self-sabotaging due to fear of success

I always felt like I was trying really hard to “get” with women. Every weekend I’d get drunk and hit the clubs (which I hated) in a desperate attempt to get near some single women who might possibly be keen.

I went to every party. I texted girls all the time. I made every girl laugh until she wet herself. I hung out with attractive work colleagues to the point of clinginess. I even went to the extent of learning to be a Pick Up Artist, such was my desperation and dedication to success.

On paper, I really appeared to be a guy who was at least trying to do better with women.

Years later, I reflected on this period of my life with a bit more attention to detail. And I noticed some unusual things.

I’d often get too drunk or high. Girls would create an opportunity, but I wouldn’t be able to transport us to a location where something could happen, or I’d unravel a good conversation by slowly becoming incoherent and weird as I got more wasted.

I’d lose interest in girls I’d previously been crushing on the moment they seemed interested or available. It’s like my attraction just disappeared in an instant once I saw there was a chance to actually do something about it.

I’d stay in a flirty phase with a girl and never allow it to get beyond playful banter into any form of serious discussion.

I went after girls who were “unavailable” in some way, from girls with boyfriends through to traumatized single moms with major emotional issues.

When I reflected on it, it was clear that some part of me was doing all it could to prevent me from connecting with women. I even would get erectile dysfunction when I pushed myself to escalate something toward sexual connection with a girl I really liked – it’s as if my body was in on the scam to stop women entering my life (I never had this issue with girls I didn’t care about emotionally).

Many Nice Guys don’t realize that they’re lying to themselves about their dating goals. They’ll tell themselves and others that they want a girlfriend or sex, and yet seem to do anything and everything to make that impossible.

They don’t realize that they have an Avoidant Attachment Style and that their Nice Guy Syndrome is really a strategy to stop people getting “in” with them emotionally (so they can’t get hurt).

Green Light Syndrome

I always thought of myself as “laid back” and “easy going”. I was proud of this trait, and often got complimented on it.

I never got angry (in a way that others knew about anyway). I didn’t care much about what happened. I was happy to follow along with the gang and do whatever everyone else wanted to do.

Years later, I’d come to name this effect Green Light Syndrome. Like a car stopped at traffic lights, I would wait patiently for a sign that it’s OK to move forward. And once I noticed this, I saw it everywhere.

It was like I couldn’t move on something unless it was pre-approved. I’d need some sort of encouraging sign that this would not end badly – with rejection, embarrassment, ostracism, or failure.

If I couldn’t get a green light, I’d stay still and wait. Sometimes I’d wait forever.

This fear of taking risks is the silent killer of a Nice Guy’s life. He tells himself that he’s cool and easy going, but in reality he’s a coward who never initiates or acts bravely in order to create a better life for himself and others. He’s limited by what’s already approved of by others.

Sexual Shame

Growing up in a macho West Auckland culture, all the guys around me talked about sex constantly. It was clearly a badge of the highest honor to have a lot of sex with hot girls. And of course, being unable to get laid was a sign of severe defects as a man.

This was so strong I was actually compelled to lie about losing my virginity just to get them off my back, because – get this – I was still a virgin at the advanced geriatric age of 15! My friends often claimed to have lost theirs and to have been having regular sex before 11th grade.

Insanity.

When I got my first proper girlfriend, I had zero sexual experience. Much to my horror, when we went to do it for the first time, my dick wouldn’t work. This began a 10 year nightmare battle with ED.

There was so much pressure to have lots of sex and to be good at it (Nice Guys feel the most people-pleasing pressure in the bedroom), that sex became a highly stressful area for me. Even when I did it “successfully” my mind was racing and I was desperately trying my best to do “well”, which killed my enjoyment of it (well, almost).

Nice Guys take sex way too seriously, and many of their dating problems actually stem from a subconscious desire to avoid sexual situations.

Allow the Friendzone to develop

I have been in so many friendzones!

In my early twenties, I went from one female “friend” to another, like a serial monogamist but without romance or sex.

I’d visit them 4+ times a week. I’d talk to them on the phone for hours. I became their best friend and knew everything about them.

And the entire time I was just bursting with desire, wishing I knew how to transition from friends to “take your panties off”. I just couldn’t pull the trigger.

And I’d inevitably miss whatever window of opportunity there was for romance, forever killing attraction by becoming a passive, asexual, platonic friend.

Eventually, the day would come when they’d ask for my advice on how to proceed with another guy that they were attracted to, and my dreams would come crashing down. Like an immature incel, I’d ghost them from that day onwards, punishing them for my mistake.

My inability to “risk the friendship” by asking for or stating what I really wanted with them guaranteed that I’d never achieve it. I’ve met up with a few of these girls years later, and they all confirmed that I’d had a “chance” with them, but they’d assumed I wasn’t keen and accepted friendship as a consolation prize.

Showing a limited emotional range

I used to wonder if I was a psychopath, so limited was my emotional range.

I spent most of my time feeling kind of mildly anxious, bored or numb. I might occasionally feel some joy, but only during extreme events like seeing my favourite band live. I didn’t cry. I didn’t care.

I did occasionally explode with anger, but that was about it.

So whenever I was dating a girl, she would get a one-trick pony: calm, unaffected, sarcastic, witty and agreeable.

Any guy who understands women will shake his head and roll his eyes reading that, knowing that this is not what a woman wants!

I lacked passion. I lacked balls. I lacked mystery and surprise. Yeah, I could make them laugh and comfort them during struggles, but that’s about all I could do. I was like a comedian who moonlighted as a therapist.

Not exactly sexy. And certainly not engaging enough to stay with once the initial shine had worn off.

Girls would consistently stay with me for exactly three weeks. It was weird how specific it always was. I could set my watch to the 21 day countdown.

Turns out, that’s about how long it takes for a girl to realize that you have no depth and that she’s seen the whole show already.

Combine that with only going for crazy unavailable women, and you have the recipe for repeatedly experiencing only very short term relationships.

Avoiding conflict and confrontation

I once walked out on a girlfriend totally thinking the relationship was over simply because we’d had a heated disagreement for the first time. I was genuinely baffled that she still thought of herself as my girlfriend after that.

Despite seeing other couples “fight” all the time, I’d always assumed that this was a sign of relationship failure, and that a good relationship was completely peaceful. So that’s what I tried to accomplish.

I was overly agreeable, often being fake and hiding my preferences to keep things smooth. I went out of my way to prevent and moderate potential conflicts, gears constantly turning in my head as I anticipated and countered possible future areas of friction.

We only had one fight in two and half years. And then, “out of nowhere” she dumped me for another less boring dude.

Without confrontation, you cannot connect deeply, and another guy will have no problem beating your connection with something deeper, even if you’ve served a lot of time together. Conflict is inevitable for any couple being honest with each other. 

It’s not about avoiding fighting; it’s about fighting well in a way that you end up stronger as a couple after.

Attracted to bad fits and unavailable women

I’m telling you; I could look at a crowded nightclub and pick out the single mother who’s abandoned her kid with grandma so that she can drop a molly and get fingered by a stranger.

I’d pick unstable girls like I had a special sonar or something.

I often prided myself on being attracted to “exciting” women – translation: women with severe emotional and attachment issues who were often quite mentally ill but socially functional.

I actually saw them as physically “hot” compared to other girls, and confident healthy women didn’t even ping on my radar… not that I was hanging out in places or with circles of people that were abundant with healthy women, of course.

My favorite was an emotionally crazy single mom who wanted to cheat on her boyfriend/husband with me. I’d take pride in dating a girl like this as a “success”.

The dark truth was that I suffered from a crippling fear of intimacy and commitment due to people hurting me when I was younger, and my attraction ensured I never got near anyone who I might become genuinely emotionally connected to. 

Refusal to take responsibility for my failures in dating

My suffering could have ended when I was a teenager. Yet it wasn’t until I was at least 25 that I started to correct my course. Why?

Because despite blaming myself and going on and on about my failures, I still saw it as something like bad luck. I refused to accept that I was the common denominator and that I needed to do something about it.

I was so attached to being the Nice Guy Who Finishes Last that I didn’t even want to give that up to become The Guy Who Actually Gets the Girl and Has A Good Life!

Nice Guys usually only come to me for coaching when they’ve already been through hell, and sometimes not until they’ve gotten divorced in their forties and fifties and finally realized that they’re doing something wrong and have been fucking this up for themselves for most of their lives.

Once you look through all these points, you’d be forgiven for wondering if I ever had any success with women!

Sure, there may have been some bad luck as well, or maybe my ears are too small or something, but overall it’s fair to say I did most of the damage myself.

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