Being single for too long can hurt, especially in the quiet moments. Here's how to deal with the pain

CNA

07-06-2025

For most of her adult life, Ms Alyssa Yeo has been single.
The business development manager is 36 this year, has a good sense of humour, is thoughtful and well-travelled. Apart from one serious relationship in her early 20s, she has no one now to call her significant other.
She has had her share of "crushes", first dates that led nowhere, as well as short-lived situationships that never turned into relationships. She has tried using several dating applications and agreed to go on blind dates set up by well-meaning friends.
Yet, after years of trying – trying to be open, to be patient, to be the best version of herself – Ms Yeo is still single.
Most days, she enjoys her own company and works hard to build a life that she is proud to lead. She also said that she would get positive comments from friends telling her to enjoy her freedom and how nice it is that she does not have to deal with diapers, relationship "drama", and in-laws.
Why, then, does being single still hurt sometimes, especially in those quiet moments, such as returning home to no one waiting, no one asking about her day and no one with whom to share a meal?
Ms Yeo said: 'It's not that I can't deal with being alone but it's lonely and depressing sometimes.
"It's hard not to feel like there's something wrong with me, or that I'm behind all my peers who are either engaged, married or already have kids, which is something that I dream of.
"I'm worried when I think about whether I will ever find someone. What if I never find someone?'
Ms Yeo wonders what it takes to be truly okay with being on her own, or if someone as emotionally needy as her is simply not built for singlehood.
The French philosopher Jean-Paul Sartre once said: "If you are lonely when you are alone, you are in bad company."
In that vein, how does one become comfortable being alone?
Counsellors said that it is common – and completely human – to wrestle with negative feelings, and that although some people thrive in solitude, others may find singlehood more emotionally challenging.
It often takes intentional practice and a shift in mindset to view this period as a season of growth, rather than one of lack.
WHY PROLONGED SINGLEHOOD CAN BRING UP NEGATIVE EMOTIONS
Relating Ms Yeo's experience to counsellors, I learned that extended singleness, especially when it is not desired, can take a psychological toll, where a person may experience low self-esteem, anxiety and shame, for example.
Consultant clinical psychologist Roy Chan, founder of the psychology clinic Cloaks and Mirrors, said anxiety stems from the desire not to be single, and it is triggered when repeated attempts at finding a partner do not work out.
'This pressure is further compounded when people give themselves a timeline to find a date.'
Dr Chan explained that low self-esteem can be triggered when people compare themselves to others in relationships and feel less desirable, or in more extreme cases, even "unlovable".
Shame, he added, often arises when these social pressures are internalised, leading people to believe that they lack the qualities or attributes that would make them attractive to the kind of partner they desire.
Mr James Chong, clinical director of counselling and psychotherapy centre The Lion Mind, said comparisons with others are often amplified by social media, where curated snapshots of seemingly perfect relationships can distort perceptions of reality.
Everyday interactions can reinforce these feelings, such as when colleagues with family commitments are given priority during holiday planning, or when workplace cultures subtly favour married workers, he added.
Mr Chong also said that some people may struggle with the feeling that they are complete only if they are in a romantic relationship.
Even those who are confident in themselves can feel discomfort when close friends start focusing more on their partners or families, and that growing distance can trigger feelings of abandonment or being "left behind" that deepen the struggle, he noted.
Some of these pressures are evolutionary. Dr Chan explained that in certain social circles or cultures, expectations to find a partner and procreate can be especially intense.
'This is especially if the culture is more group-focused, where dating and procreation are seen as a contributor to the longevity of their tribe and genetic code.'
Even older relatives who pressure you to settle down may be doing so from a subconscious drive to see their genetic line continue, Dr Chan added.
On whether certain personality types thrive better in singlehood, the counsellors had differing views.
Mr Chong said there is a common misconception that introverts are naturally better at being alone.
'While introverts may prefer less social stimulation, they still require meaningful connections and are not immune to feelings of loneliness.'
Most people still have an innate need for connection and belonging, he explained.
Dr Chan, on the other hand, believes that some people, particularly those who are introspective, genuinely thrive on their own and do not equate being alone with loneliness.
'They are less likely to use social connections as a benchmark of self-worth or social success, and they can be more satisfied with their thoughts and activities that they enjoy.'
GETTING COMFORTABLE WITH WHO YOU ARE
So, what does it mean to thrive alone as someone who is perpetually single and can it be fulfilling?
Psychotherapist Jeannette Qhek, founder of the wellness space Chill by Nette, said that it sometimes helps to step back and look at where we are through the lens of broader psychological ideas that reframe singleness not as a void but as a meaningful phase of growth.
She pointed to Maslow's hierarchy of needs, which theorises that although romantic love can meet humans' very real need for connection and intimacy, there is more to life than just a romantic partnership.
Maslow's hierarchy of needs is a psychological theory that organises human needs in a pyramid, starting with basic survival needs such as food and safety, and progressing to higher-level needs such as love, esteem and self-actualisation.
The idea is that people are motivated to fulfil lower-level needs first before they can focus on more complex emotional and psychological goals.
'The top of Maslow's pyramid, which is self-actualisation, can often be most powerfully accessed in states of solitude, introspection and spiritual practice. In solitude, we sometimes hear ourselves more clearly,' Ms Qhek said.
Then there is attachment theory, a psychological framework that identifies different attachment styles – secure, anxious or avoidant, for instance – that influence how people connect with others in romantic, platonic and familial relationships.
Ms Qhek said this theory teaches us about the patterns we have developed in relationships: how we reach for closeness, how we protect ourselves and how we respond to emotional risk.
'But one of its deeper lessons is that the most important secure bond we can build is with ourselves. Being single gives us space to create that inner safety, where we feel worthy and whole regardless of who stays or leaves.'
And then there is the famous psychologist Carl Jung's idea of individuation, which is about becoming your fullest, whole self, Ms Qhek said.
'That process often begins when we stop seeking someone else to 'complete' us and start asking, 'Who am I, really?'
'This might mean confronting your own shadow, the parts of yourself you've ignored or pushed away... Singleness can be the very terrain where that deep work begins without the distraction of projecting it onto a partner.'
Ms Qhek added that being single is not a pause on life, because it might be the very season that shapes you into the person you were always meant to become.
HOW TO MAKE PEACE WITH BEING ALONE
Of course, growing comfortable with solitude is not automatic. As with most things in life, it takes practice.
The counsellors suggested starting small, such as going out to have a solo coffee "date", watching a movie in the cinema alone and going on a staycation where you don't have to compromise with anyone else's schedule.
Mr Chong also said that it can be helpful to look at singleness as a season of self-discovery and growth, rather than a sign of lack or incompleteness.
'Community groups, religious fellowships, hobby clubs or even fan clubs offer a sense of belonging and shared purpose.
"A secure sense of self-worth can also be cultivated through personal achievements, learning new skills or contributing to meaningful causes,' he added.
'Ultimately, self-worth should be anchored on who the person is, rather than whether the person is romantically desired by another.'
Similarly, Dr Chan said that people can view solo experiences as unique and valuable opportunities to connect with themselves and the environment around them, which is unconstrained by another person's expectations, especially in a romantic relationship.
'There is joy in looking at the waves crashing along the Californian shoreline, or a late-night walk through the street stalls of Namdaemun, Seoul, where one is free to stop and linger for as long as the person wants, just looking and noticing the people,' he added.
'It's almost as if they are watching a movie, where they are the only audience. These are activities and really unique experiences that cannot be done with a partner.'
Ms Qhek highlighted that it is not just romantic partners who can be sources of validation or companionship.
'Build a circle of intimacy beyond romance. Invest in deep friendships, community and chosen family. Emotional intimacy doesn't only come from romantic partners, as there are many ways to feel seen and supported.'
More importantly, a period of singlehood is a time when you can work towards understanding yourself better.
Dr Chan said some people start to wonder if they are being too picky or asking for too much when they are actively looking for a partner but have not found one yet.
"But it's not just about what you're looking for. It's also about knowing yourself.