So, you are an introvert man, a master of avoiding eye-contact and making small talk seem like learning to speak mandarin – but in approaching women, you are interested. But, why is it that the introverted guy who flinches at small talk with a waitress to order food, suddenly considers asking out a goddess-level stranger at a bus stop?
That’s what I found myself thinking a couple of times throughout my early adulthood. If I am more comfortable and energetic in my own company my own space, what motivates me to go for such an un-introverted mode of socializing with the opposite sex – if it entails the dreaded small talk.

Confidence? Never Heard of It
Firstly, approaching women is largely about self-confidence. Though, confidence is often portrayed as a loud and extroverted trait, for some functional introverts like myself, it’s more like a keel of a ship — subtle, but impactful to personality. In fact, when I became aware of my own self-confidence and assuredness, it helped to create my own unique charm. A charm I leveraged to motivate me when approaching women. Let’s take James Bond for a moment, confident, mysterious and quiet; an introverted personality that made every girl go crazy (fictionally). Bond remained mysterious, badass, confident, introverted and very confident making him irresistible to every woman, and this transcends fiction. In reality, introverted men can have unique qualities that people may find appealing.
The Inner Dialogues of Doom
The mind of most introverts is a twisting labyrinth of overthinking. Should you approach her? What if she thinks you’re weird? What if she doesn’t? It’s a cycle of self-doubt and hypothetical scenarios for many men. It’s ten-fold and amplified with the weight of inaction and shyness. You have to learn some element of control or awareness of how to control it. To overcome this, I had to understand one thing – accepting/being aware that I overthink. Too simple? Not exactly. Overthinking is a habit, so like any over-indulged habit, I had to form a “counter-habit”. In this case of approaching women, my counter habit was to get them to want to talk instead, and not me continuously probing away with questions and multiple choice answers in my mind (like the actual convo happened). I started with a simpler objective – approaching women should get them to want to talk. Besides, it’s the best way to find out if she may be deceptively boring.
Tactical Approaches to Approaching Women
After learning a trick or two in keeping it simple when approaching women – you can start small. A simple “Hi” can be more effective than a grand gesture with a Disney movie royal fanfare. Observe her interests and comment on them, get her to ramble about it, well the narcissistic ones will. It’s like shopping; sometimes, you compare similar products for different things, brand equity, price, quality, value etc. The point is, when you take an interest, intuition helps to identify openings to approach her. It largely works in motivating me for an approach, however there are other factors (external) to still consider.
When the Introvert Actually Scores(ish)
And, miracles do happen. You have now been motivated and you have approached her, she responded positively, and suddenly, you’re in a conversation finding out where the commonalities are. It’s like overcoming an infant’s fear of walking on your own —rare, magical, and slightly terrifying. There have been instances where I employed what I mentioned earlier and let the hallmarks of good and clever communication take hold to act as the motivational vehicle of discourse, penetrating the veils of interest. With the only issue being, if I will find them boring after I get them to talk 🙂 . Or, if she is extroverted suck the room out of the air (you read that right). Not so much as, “what do I need to say or not say”. Nah, instead I find that I have to change my objective when I engage to something like “fluff reduction”.
The Aftermath of Approaching Women – Ghosting (take a breath)
After the interaction, I would often retreat to my “den of thoughts” to reflect, over-analyze, and vow to never do it again. That is, until the next time where I find myself with the insatiable urge for approaching women. It’s a fact that once you get into talking, because we hardly engage, we need period of analysis to confirm if this is/was a valuable use of time to “get to know” someone – ugghh, small talk. After all, as introverts we need to feel ‘energized’ by a conversation to even want to continue. Realising that you are working with your own clock, is all the pressure that you need in determining if the approach should need a re-approach.
Final Irony: You’re Charm in Approaching Women
So, the paradox is real – your introverted nature, your thoughtful silences, your careful words, your pragmatism — they’re not weaknesses. They’re your superpowers. Embrace them when approaching women, but keep it simple. Or at least, keep each objective simple.

The Smart Dimwhit is a fun loving blogger who speaks about extroverted life situations from the perspective of an introvert, with random musings and terrible humor. Follow him on Pinterest, Instagram or Facebook, to keep in touch.


2 Responses
TheSmatDimeHit.com delivers an insightful and refreshingly candid take on the inner world of introverted men navigating the often intimidating process of approaching women. With a voice that’s both introspective and self-aware, the site explores complex themes like self-confidence, overthinking, and the subtle charm of introversion—without falling into clichés or shallow dating tropes.
What stands out is the raw honesty: the writer doesn’t mask the anxiety or awkwardness that can come with social interaction, particularly with romantic intent. Instead, he reframes those traits as quiet strengths, showing that introversion can be a unique advantage. The tactical advice offered—like simplifying objectives and letting women do the talking—feels genuine, grounded in personal experience, and refreshingly free of bravado.
Ultimately, TheSmatDimeHit.com resonates for its relatable humor, depth of thought, and ability to connect with both men looking for guidance and women curious about the often-unspoken male perspective. It’s a thoughtful read that redefines the rules of attraction, especially for those who don’t thrive in the spotlight.
Thanks so much Andre :-). We will keep them coming