Dating. Or dating after a breakup can feel like such an emotional rollercoaster, one moment things feel close, the next they pull away. It leaves you wondering what’s real, what’s not, and why it keeps happening. This reflection looks at how anxious, avoidant, or secure attachment styles quietly shape the way we date, the people we’re drawn to, and why those mixed signals can leave us questioning ourselves, so you can start to see the patterns, understand what’s really going on, and feel more clarity (and a little more calm) in the chaos.
Here’s why I believe dating is getting harder…
So last week, I was interviewed by a journalist to feature in an article about modern dating struggles in Dubai and beyond!
In short, I was thinking how we are all ‘Red Flags’ in some form or another.
We all have our quirks, past hurts, and heartbreaks of some kind or another, and I created the metaphor that we are all walking around with emotional baggage, rucksacks on our backs, filled with more and more pebbles over time. Which gets heavy. And continues to get heavier if we ignore the inner work and the deeper self-reflection needed for healthy relationships.
So why is dating seemingly getting harder!?
I hear so many stories from my clients and wider community that meeting somebody who we truly vibe with, feel attracted to, hits our relationship non-negotiables and where we can be our true selves (and feel emotionally safe) seems impossible as we continue to navigate the modern dating scene.
Swiping, dating apps, and relationship myths have become a part of what we actually believe to be true or right. But what happens if what we thought was true… wasn’t?
What happens if we are actually the red flag (no matter how small or large) and we are not showing up in the healthiest, most emotionally available way?
What happens if yes, we have the career, we train, we dress well, we have interesting hobbies etc. etc., but still cannot find that meaningful, long-term relationship?
What are we missing?
Yesterday I watched the new movie A Big Bold Beautiful Journey with Margot Robbie and Colin Farrell, and it was almost like seeing the journey of so many of my single clients.
The rucksack of pebbles which we have been carrying around with us for years, not addressed, but compartmentalised and shoved down (in a bid to move on and forget), but actually continues to show up in how we date. How we are too much, or too little. How we actually end up performing, or showing a mask, rather than knowing who we are and being authentically ourselves in relationships.
So many of my clients come to me with ego: “I know my worth,” “I’m doing XYZ,” but why do I find myself in the same repeated dating patterns? A different person but the same dead-end relationship or the date that never gets past two or three meet-ups?
And then, our rucksacks get heavier. More pebbles.
That negative comment, being ghosted, the next break-up or the promotion we didn’t get. Heavier. And more of the ‘red flag’ we become.
Because then we start to question ourselves, ‘What is wrong with me? Why am I still single? Am I not enough?’
Then maybe we meet somebody, and we go, oh gosh, I cannot fully lean into this because the risk of being heartbroken again, or the risk of feeling hope, happiness, and togetherness—will be too painful if the rug is taken from under me again.
Sound familiar?
When we are single, we often compartmentalise dating and avoid close connection for fear of what further hurt or disruption this will bring to our lives (and our rucksack).
So we date on the surface, which forces us to stay in emotionally unavailable relationships, have low levels of emotional investment, or we are led by our insecurity where we stay and pursue the unavailable partner because of our deep-rooted fear of loneliness or our need to strive for external connection to prove our worth or our enough-ness.
So we approach dates with all the bells & whistles, which blinds us to the reality of the date in front of us, who may be lacking real emotional intention.
And instead of working on ourselves to address what’s at the core of these beliefs, many single men and women armour themselves with high standards in dating and pre-requisites masquerading as confidence, when underneath there’s still fear and avoidance.
As soon as my single clients stop repeating their past relationship patterns, work on becoming more securely attached, and learn to date from a place that isn’t fear or avoidance, real emotional connection opens up.
Many get stuck in this false-staged dating world, the swiping-app culture, or the ‘I know my worth’ mindset that expects expensive first dates rather than authentic connection.
But let’s think about this for a second: is any of this real intimacy?
Dating past 30 can feel harder because we’re not naturally in new social communities like we were in our teens or 20’s, so we don’t meet as many people organically.
But if we start re-entering social activities the way we did when we were younger, we will naturally feel less pressure and start to form authentic relationships over time.
When we start having honest conversations with our ego, maybe it reveals the uncomfortable truth that we are showing up in dating with our own red-flag behaviours.
It’s always easier to blame the other person, ‘she’s crazy’ or ‘he ghosted me’, but is it our own unhealed patterns, our dating mindset, or our relationship fears that are actually sabotaging the people we attract, who we are attracted to, and more importantly, how we show up in relationships?
A Gentle Next Step
If you’re feeling caught in the confusion of dating, or unsure how to find your footing after a breakup, I’m here.
Whether you want to use the term psychologist, psychotherapist or coach, whichever makes you feel more comfortable in helping to tackle the relationship with yourself and others I am an online relationship therapist which can help you understand behaviours which may be effecting your marriage, relationship or dating habits.
Best wishes,
Charlie.
Psychologist, Therapist, Coach based in Dubai providing global online therapy to those in need.
We don’t need to hurt.
#relationship expert
29 September, 2025