After years of coaching men — across cultures, ages, and life situations — I’ve identified 13 core pain points that consistently show up when men can’t seem to make things work in dating, relationships, or finding a life partner.
This isn’t a list designed to make you feel bad. It’s a diagnostic — a way for you to locate where your real friction is, so you stop working on the wrong things and start making actual progress
Not every point will apply to you equally. A man with an active social circle has a very different starting point than a man living in a small city with limited dating options. Context matters. That’s why this isn’t a checklist — it’s a personal audit.
There’s a self-audit exercise at the end of this post — once you’ve read through all 13, use it to score yourself honestly.
1) Programming and Conditioning
Each person’s programming is unique, shaped knowingly or unknowingly from early childhood.
When it comes to how men should relate to women—how they should behave, what attraction means, what women want—many men are programmed and conditioned in ways that ultimately hinder their success in dating, sex, relationships, and marriage. Some of this programming is outright wrong, some is outdated, and some is cross-culturally limiting.
Words like “creepy” and “inappropriate” are frequently used during this conditioning process. Most commonly, boys are taught to feel shame around their desire for women.
This shame becomes deeply embedded and surfaces later in life, creating barriers when men try to connect authentically with women.
2) Lifestyle and Ecosystem
This may not apply to most men worldwide, but many face genuine challenges due to limited access to women or insufficient opportunities to socialize. Sometimes it’s the nature of their work; other times it’s the city they live in.
We all know some cities have a thriving social scene and active dating app culture, while in others, finding matches is significantly harder. Though not universal, these lifestyle and ecosystem disadvantages create real barriers for many men.
3) Social & Contextual Intelligence
Social & contextual intelligence does not come easy to us. It has to be honed, trained and developed. To have a way with women, be it online or offline, a man must have some degree of social & contextual intelligence.
Social & Contextual Intelligence is a man’s ability to read the room, read the woman, and read the moment — and respond in a calibrated, and socially aware manner. This applies both online and offline.
Somehow men in their life journey have missed out in developing this requisite intelligence. It is not only universally appealing, but also necessary now a days.
4) Social Courage and Action
For some men, sending a DM or approaching a woman can feel like moving a mountain. While it comes easily to a few, most require significant energy and self-talk to take action—especially in person.
The fear of minor embarrassment often leads to missed connections. The inability to move forward despite feelings of fear, anxiety, and self-doubt has been a significant pain point for many men I’ve worked with as a coach.
5) Personality & First Impressions
Of all the pain points, this one is unforgivable across contexts and cultures.
A bad first impression is difficult to recover from, and a weak or subdued personality will hurt your chances no matter where you are. People form judgments within seconds of meeting you, and these initial impressions are sticky—they colour every interaction that follows. A subdued, low-energy presence signals disinterest or lack of confidence, which kills attraction before it begins. The challenge is that you can’t negotiate your way out of a bad first impression with logic or later demonstrations of value.
That said, what constitutes a great personality or strong first impression is somewhat subjective—so aim for qualities that are broadly appealing rather than niche or polarizing.
6) Mind-sets & Thought Process
In any aspect of life, no matter how great your technical or operational skills may be, without a favorable mindset and thought process, you can’t go very far.
In the context of dating and relationships, mindset refers to how you think about yourself, male-female dynamics, women in general, sexuality, and the values and principles that guide your approach to companionship.
For instance: believing you’re unworthy of a relationship, holding outdated views on sexuality, being overly rigid about values in today’s dating landscape, operating from a fixed mindset rather than a growth mindset, or thinking it’s a waste of time to work on yourself—all of these create barriers.
Certain mindsets simply don’t allow men to thrive in dating and love. Mindset issues and outdated thought processes are among the most common pain points I see.
7) Inner Voices
Self-doubt. Lack of self-trust. That voice in your head that says you’re not enough.
For most men, this inner voice is a top-5 pain point. It sabotages confidence, kills momentum, and keeps you stuck. Here’s what most don’t realize: that voice isn’t yours. It’s conditioned.
Childhood criticism. Past failures. Social messaging. These experiences hardwired a narrative that now runs on autopilot—telling you you’re not ready, not worthy, not capable.
Some of it comes from real setbacks. But most of it? Borrowed beliefs that were never yours to begin with.The gap between where you are and where you want to be often isn’t skill, effort, or opportunity. It’s that voice.
The last mile is getting your inner dialogue to work for you instead of against you. And that starts with recognizing: you don’t have to believe everything you think.
8) Emotional Intelligence
Women have a natural advantage here. And in relationships, that creates a gap men need to close.
Emotional intelligence is recognizing your emotions, expressing them without losing frame, regulating yourself under pressure, reading others accurately, and responding rather than reacting.
In casual dating? You can coast without it. In serious relationships? It’s everything.
Without it, you’ll misread her, escalate unnecessary conflict, and watch intimacy fade—wondering what went wrong.
The men who develop emotional intelligence don’t just keep relationships intact. They lead them.
It’s not soft. It’s strategic. And it separates men who struggle from men who thrive.
9) Presence & Vibe
“He’s not my vibe.”
You’ve heard this. Maybe even heard it about yourself.
Here’s the truth: your vibe isn’t some mystical energy—it’s the signal you broadcast before you say a word, and even after you start interacting.
It’s your posture, your eye contact, the tension (or ease) you carry into a room. Whether you’re comfortable in your skin or performing for validation, or least bother. It’s also your flair, a healthy entitlement, if present that counts.
People filter by vibe instinctively. Especially women. Especially as they get older and more selective.
Most men ignore this. They optimize their words, their style, their résumé—and wonder why connections fizzle.
You can have the right credentials and still feel off. She won’t always be able to explain why. But she’ll feel it.
10) Sexual Instinct
The modern era is filled with men who are disconnected from their sexual instinct.
This disconnection happens when a man has learned—through shame, rejection, religion, culture, or past trauma—to push down, deny, or suppress his natural sexual drive. It shows up in his body language, tone, and behaviour as a certain passivity or hesitance in his sexual energy around women.
The flip side is equally problematic: being overly consumed by raw, animalistic impulses. This represents a different form of disconnection—one that lacks calibration, nuance, or emotional intelligence.
Healthy sexual instinct sits between these extremes: present and confident, but also attuned and intentional. Disconnection from this balanced sexual instinct is an overlooked pain point, yet in my experience as a coach, it ranks among the most critical.
11) Tactical – Technical Know-How
This is an obvious pain point, yet critical. We’re talking about the intelligence and creativity required to understand and adapt to the nuances of female psychology, emotional states, and conditioning.
We’re talking about timing, framing, escalation, social awareness, pacing, texting, presentation, positioning, and both verbal and non-verbal communication skills.
No man is a complete natural at this. We all have to learn, whether consciously through deliberate practice, subconsciously through trial and error, or—for the rare few—through early guidance and training.
12) Faulty Maps
A map is your internal user’s manual—the mental model you carry for different aspects of life. You have a map for how to make money, how to deal with people, how to navigate career challenges. Some of these maps are consciously developed; others are unconsciously borrowed from culture, family, or peers.
Similarly, every man has a map for how attraction works, how to pursue women, and how connection unfolds. In my years of coaching, I have rarely come across a man who doesn’t have a faulty map in this area.
A faulty map leads you to work on the wrong problems, invest energy in the wrong places, and wonder why effort isn’t translating into results.
13) Free-Spirited
It’s only in recent couple of years, I have discovered the issue of lack of free-spiritedness among men.
The heavy energy, constant seriousness, a strong ego, taking things personally are a constant among some men.
Free-spirited men come from a very different internal place. They love to be open, expressive for themselves. They do not take things personally. They have a capacity to make fun of themselves.
Men with free-spirited energy tend to do very well with women, and lack of it requires a lot of compensation in other aspects.
Move to page 2 for the exercise.
Leave a Reply