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‘I’m easy-going, intelligent and apparently good looking – so why am I single?’

Ask Roe: I see the wonderful people my friends are with, and think, ‘Why can’t I have that?’

Dear Roe,

I’m a 30-year-old straight female. I’m easy-going, social, intelligent and apparently “good looking”. People always ask me, “How are you single?” It’s a question I ponder myself. My last formal relationship was during secondary school. Since then, I’ve casually dated people but never felt enthused enough to label things.

As friends begin to settle down, I’m anxious about the closing window to meet someone. Attending engagement parties and weddings, I look at my friends and I see the wonderful people they are with, and I think, “Why can’t I have that?” or “How can I have that too?” By now, I understand that I hold the power and answers to my “single situation”.

I invest a lot of time working on myself through writing, meditating and reading to try understand myself more and become a better, more accepting person. So far, it has not brought me closer to finding a true connection. Unfortunately, I am attached to a checklist of things I’m searching for in a partner. I justify it as I work so hard to create the life I have, that I feel deserving of someone who has done the same. I recognise this idea is harmful and makes me hard on people. What work can I do to change my situation, mindset and find love?


There’s so much that I love about your letter. I love your confidence, your self-sufficiency, your drive to build the kind of life you want and your investment in trying to become the best version of yourself. You have so many admirable and impressive qualities.

But do you know what I find interesting about your description of your life? How end-goal focused it is. You read and write and meditate to “to try understand myself more and become a better, more accepting person”. This sounds noble – and somewhat objectifying. You have latched on to a formula that you believe will make you “better” – turning simply existing as yourself into a measurable test.

You’re focused on self-optimisation, but how much have you embraced self-exploration? You read, you write, you meditate – but how do you feel while you’re doing them? Do you feel emotionally connected to yourself, to the world, or do you feel like you’re successfully checking tasks off a list?

Everyone learns so much about themselves in relationships, yet you’re shutting down these opportunities

How often do you try things that are out of your comfort zone? How often do you do things where you’re not completely in control, things that you are not good at? And, importantly, how often do you try or invest in experiences with other people? All of the activities you have listed are solo activities, which is of course not inherently a bad thing – the ability to enjoy solitude and feel fulfilled is important and wonderful. But I wonder how often you’re engaging with other people, learning how to sit in their gloriously flawed humanity and yours, learning how to appreciate people who are different than you, learning how to enjoy relationships and experiences where you can’t control everything and there isn’t a goal to be reached, merely human interactions to experience and grow from?

Your relationships with other people, your ability to embrace new experiences, and your dependence on control have a lot to do with your approach to romance. Right now, you’re looking at love like a mathematical formula with a predictable equation. Good Looking + Intelligent + Self-Improvement + 30 Years Old = Should Have A Partner [with XYZ qualities]. But what is missing from your equation are the most important things: curiosity, vulnerability and effort.

You’re not curious enough to want to learn how to be in a relationship; what you could learn from other people; and what you actually like, value and need in a relationship that exists in real life – not just on paper. It’s not just that your checklist for a potential partner “makes you hard on people” – it leaves no room for curiosity. You have decided what you need in a serious relationship without ever having one. You have decided what kind of person is best for you without being curious enough to give different kinds of people a chance, to see how you respond to them, what you can learn from them, what dynamics bring out new and interesting and even flawed sides of you.

Everyone learns so much about themselves in relationships, yet you’re shutting down these opportunities. You invest in reading about and intellectualising relationships, but you aren’t curious enough to move out of the realm of theory or solo self-optimisation and commit to people in an embodied way. You have shut down your curiosity about experiences other than the ones you can control in your own mind.

There’s a lack of curiosity here – but also a lack of vulnerability. You and your checklist work together to create a wall, giving you endless reasons and excuses not to get serious with anyone. This isn’t simply because you have high standards – most people have standards. But your self-image is so rooted in the idea of being self-sufficient that you’re terrified both of letting someone into your life and disrupting the control you have there, and of the vulnerability that comes with trying something new for the first time.

You haven’t seriously been with anyone as an adult. The first new relationship – the first several relationships – will all be a huge learning curve. You’ll have to commit to the process: to flailing around and making mistakes and feeling uncomfortable and opening up to someone, to possibly not being the perfect partner at the beginning. And I think not being perfect scares you. The vulnerability of being new to something – new to love and relationships – scares you. But there is no real connection without vulnerability. It doesn’t exist. And you’ll never learn how to be vulnerable with someone by reading a book. You have to try it in real life, and keep trying, and you will get hurt, and you’ll have to decide not to shut yourself down and keep being vulnerable and possibly getting hurt again because that is how you learn, that is how you grow, that is how you love.

Finally, you need to put in the effort. You need to do the work. This seems like a ridiculous thing for me to tell you, the person who always works hard – on yourself, at everything. But when it comes to relationships, you think you are somehow above making the effort. You look at your friends who are coupled up and you are envious of the whole package, wondering why you don’t have it. The answer is simple: you aren’t putting in the work. The work of dating, of sticking around with someone, of trying to build a connection and a relationship with someone.

You feel entitled to having a serious relationship with a checklist-ticking person delivered to your doorstep without doing any of the work of slowly building a connection, enduring and navigating the initial awkwardness of dating, the emotional vulnerability of deciding to commit to someone, the challenges that come with a more serious relationship, the curiosity and commitment and effort that is required to build something – and sometimes the work and hurt of deciding that it isn’t working, and the resilience to try it all over again.

You have spent your entire adult life so far committing to learning about yourself and I get the impression that you believe that you’re basically done: self-optimisation levels completed! But the truth is, you are only just starting to learn about yourself, and getting out dating and trying relationships is going to teach you more than you could possibly imagine.

Be curious, be vulnerable, do the work. It’s going to blow your whole world wide open. It will be amazing.