Top image: Benjamin Tan / RICE File Photo
Sarah* wipes the sweat off her palms. She’s putting on lipstick for the first time in what seems to be a decade. She’s wearing a nice patterned blouse—the one she shoved at the back of her closet because she stopped feeling sexy enough to wear it.
She meets her Tinder date, a man in his mid-forties, at a random Italian restaurant on Orchard Road. He pulls a chair back for her; chivalry she hasn’t experienced in a long time.
When she describes it to me, it sounds like a coming-of-age movie. I have to remind myself that she’s 55.
Based on the sheer volume of matches Sarah gets (at least five to ten a week), she’s not the only older single swiping for love. But this isn’t a generation that often makes the news when it comes to online dating.
Gen X (aged between 44 to 59) may be a quiet minority in the Singaporean dating app scene, but their numbers are nothing to scoff at—16 percent of Gen Xs surveyed claim to have downloaded a dating app. That’s around one auntie or uncle for every big extended family gathering, discreetly swiping away.
With marriage rates down and divorces on the uptick—not to mention the rise of single ladies choosing to stay unhitched and uncommitted—it’s natural that there’s a growing share of people without someone to grow old with.
But what the demographics don’t tell you is how we’re coping with this growing singlehood. And for our older single Singaporeans, dating apps are one of their last-ditch attempts at solving a potential life-long loneliness.
Dating: Chance or Choice?
No one really associates singles in their fifties with dating apps. Apps are unsurprisingly more popular with millennials and Gen Zs—chronically online generations who are typically less fussed about ‘meeting someone organically’.
But I quickly learn from Daniel*, a 51-year-old Casanova, that meeting through circumstance these days is way harder than it used to be.
He was a lifelong single until he met his current fiancée through a Mobile Legends (ML) online community in 2020. After their online introduction, they finally met at a bar to get to know one another and, of course, play a few games of ML.
Despite the fact that David has game (in more ways than one), he had spent at least eight years on a variety of dating apps and Facebook dating groups.
“When I was online dating, a lot of girls would message me first,” he says a little smugly. He tells me it’s not a common experience for men on apps. He also wasn’t interested in “going after young girls” and set his age range to women around 40 to 55 years old.
For Daniel, a busy manager with an unstable work schedule, finding his second half wasn’t always a priority. In his youth, he had a number of casual relationships, but there wasn’t time to nurture a lasting bond. Sacrificing your personal life for your professional one? A pretty common trade-off for any working Singaporean.
But in the blink of an eye, Daniel found himself turning 40, financially stable but utterly alone. Turning to apps was a desperate, last-ditch attempt at finding love, he laments.
“You can’t just go out and hit on girls anymore. Everyone’s busy and too old for that. I had to put myself out there online and do something about being single.”
He acknowledges there’s some irony to his statement. He did meet his fiancée by chance, after all. But he emphasises that he lucked out after decades of singlehood and isolation. Even then, he only found his fiancée when he went online.
Compared to Daniel, Wan Ting*, a 58-year-old who works in the property industry, is a relative newbie to dating apps. The divorcée tells me she downloaded Tinder in April last year. A friend of hers, who’s around her age and also single, encouraged her to download a dating app to move on from her ex.
Sarah, a preschool teacher, was also goaded into downloading Tinder by her 23-year-old son. She was unceremoniously dumped after 25 years of marriage when her husband left her for another woman.
Both divorcées tell me they downloaded an app pretty much within six months of their split. The apps keep them busy meeting people too: Sarah’s usually talking to one or two guys at any given time.
Wan Ting’s DMs are no less dry—she’s on roughly two dates a week. She sets her dating app to only show profiles 20km from her house and prefers meeting in her neighbourhood.
Wan Ting has tried out the whole gamut of apps available. Tinder, Coffee Meets Bagel, Bumble; the names just spill out of her mouth. She shrugs when I ask her why she downloaded so many apps.
“I gave matchmaking a try. Paid them a lot of money and they still didn’t manage to find anyone for me,” she says matter-of-factly.
Matchmakers are a costly risk: you’re often investing upwards of $1000 just to maybe meet someone compatible. Even though the odds of finding someone decent on an app are not great, at least swiping is free and extremely convenient. And the constant engagement of swiping, matching, and talking gives them something to fuss over other than the prospect of being alone as they slowly edge into their 60s.
For me and my fellow Gen Zs, dating apps are honestly taken for granted. It’s just another way to meet new people or even a quick fix to momentary horniness. It’s never been that deep for us.
But I’m quickly realising how much they can do for a lonely Gen Xer. Think about that uncle or auntie who’s always flying solo at family gatherings. Maybe they deserve to swipe around and find someone to meet the family, too.
Left On The Shelf
That said, it doesn’t mean they unequivocally love the dating app experience.
Both women are quick to complain about their worst dating app experiences. The men are ugly, or they pick photos from when they were younger and better-looking. They’re afraid of scammers.
Some guy even asked Wan Ting to marry him on their first date.
“Yeah, that’s pretty common,” she tells me, blowing past the whole ‘proposing-on-the-first-date’ thing like it’s no big deal.
“A lot of the men are needy and want to settle down quickly. And if they don’t, they usually just want to have sex.”
Daniel provides a little perspective. “Yeah, my guy friends around my age use dating apps just for sex. Even the married ones. They purposely swipe on domestic helpers or foreigners so they can hook up.”
The associations between dating apps and casual sex persist even with the older users among us. And it’s this association that partially informs their awkwardness when they talk to me—like they’re opening up about this for the first time.
Wan Ting visibly recoils when I ask if I can see what her dating profile looks like. She has deleted the apps for now, but admits that she still uses them on and off.
“I don’t usually like talking about (using dating apps) to anyone.” Our conversation suddenly takes a somber turn.
“Being single at my age, it means that no one wants me. Overlooked because I’m unattractive. I’ve been left on the shelf.”
It’s a sentiment that kept coming up while I worked on this story. I had at least four interviewees pull out right before an interview, citing how embarrassing it’d be if anyone ever found out they were using an app. Even Wan Ting makes me promise I’ll keep her completely anonymous.
It’s not just shame. Some have emotional baggage from previous failed relationships. Sarah, for instance, tells me about the insecurities that come with being divorced.
“I got divorced at the start of 2019. That whole year, I was a wreck, telling myself I’d never get married again because I’m unlovable.”
Both Sarah and Wan Ting share that since they were previously married, they know it’s harder for them to find love. They believe that no one wants to date someone who’s failed at marriage or, in Sarah’s case, comes with the added burden of kids.
For them, the shame and embarrassment isn’t really about being on Tinder. It’s about still being single after decades of trying to find happiness.
Here’s the thing: these Singaporeans come from a generation that envisioned marriage as one of life’s most crucial milestones, treated with the same level of importance as getting a job. Not only did their prime dating years in the late 80s and early 90s coincide with pro-natalist policies; it was a cultural expectation that one should settle down, secure a flat, and have kids.
Singlehood makes them feel as though they’ve failed.
But really, they haven’t failed at all. From what I observe, all of them are successful adults with stable jobs, a paid-off mortgage, and, in Daniel’s case, a thriving hobby. Other than the issue of their relationship status, they’ve pretty much made it as far as the Singaporean Dream goes.
And it’s not like they’re unattractive, either. Sarah tells me how important dating apps have been for her self-esteem.
“I knew women got lots of attention on dating apps, but it was still shocking to me when men reached out. Tinder showed me that an old auntie like me can still be sexy.”
People using dating apps for validation isn’t anything new. But for a divorced mom like Sarah, who hadn’t felt flattered in years, it’s a well-needed boost to her self esteem. The feeling of being wanted can have profound effects on depressed and lonely singles in their fifties.
Dating with Adult Money
Despite all the shame and frustration they might feel, dating apps have provided an unexpected amount of fun.
“(My friend) looked like she was having fun meeting new people on Bumble. I wanted that for myself,” Wan Ting tells me.
Chatting with and meeting new people, dressing up for dates, being excited to hold hands—Sarah tells me she feels like a teenager again.
“After being married for 25 years, I think I let go of myself a little. Got used to the stale married life. But I think I’m rediscovering this fun and exciting part of myself,” she remarks.
“I didn’t think I’d ever feel butterflies at 50. But on dates, I find myself having to excuse myself to the toilet because it’s so nerve-wracking and exciting.”
And it’s not just the hand-holding that makes them feel like a kid again. It’s this liberating self-discovery that reminds them of their teenage years—having the freedom for the first time in decades to find out who they truly are beyond just being a ‘spouse’ or ‘mother’.
Blushing aside, they’re still middle-aged singles; they’re ostensibly more financially stable than they were at 18. And their finances have changed the way they see dating.
Sarah’s a great example. She likes nice candlelight dinners in the Central area with intimidating prices and taking strolls by the Singapore River while eating ice cream. But for all her love of tradition, Sarah insists on paying for her dates: “If he pays, he might expect something from me or think I need his money. I’d rather pay and have more control over the date.”
Decades of failed experiences have made Sarah antsy to rely on someone. It’s what makes her eager to flash her credit card, as if to tell her dates she doesn’t need them. Her financial independence also allows her to be pickier than when she was younger.
“My mother matched me with my ex-husband, who was the son of a family friend. I was 30, and she told me I was too old to be unmarried,” Sarah says.
“Look at how that turned out. This time around, I want to make my own choice.”
But while they’re taking their time to sift through the admittedly shitty prospects on the apps, there’s a palpable sense of urgency—especially when they talk about their impending retirement.
“I want to believe in a romantic destiny, but I’m approaching my 60s. I don’t want to spend the rest of my life alone,” Wan Ting says frankly. “What if I get sick? Or something happens to me at home? Who’ll take care of me?”
Daniel has a similar take. He spent most of his adult life going to work, watching TV, and getting drunk alone. He wasn’t keen on repeating that same routine for the rest of his life.
He says sagely: “Some part of me still believes in destiny and fate. That’s how I met my future wife. But you also have to try to find people on your own.”
We’ve all read the horror stories of people living and dying in solitude. It’s an increasingly common reality in a Singapore that’s lonelier than ever.
Maybe it’s the longing for companionship. Maybe they aren’t comfortable being alone. Whatever it is, this fear of loneliness has bred optimism in our older singles—they haven’t let go of the idea that love still exists out there for them. That they’re still lovable.
Hopeless Romantics
Daniel asks me what dating apps look like now. I tell him how Bumble now has another version just for finding friends. He gets excited at this and nudges his fiancée: “Eh dear, we can use (Bumble BFF) to find more friends to play Mobile Legends.”
I feel like I’m watching Gen X catch up to technology that’s already second nature to us.
Yet they’ve also crafted a deep appreciation for dating apps that no one in my generation has. In fact, just as older singles hop on the Bumble bandwagon, youths seem increasingly disillusioned with dating apps. Maybe the romantics in us have died; we’re okay with staying single, or we just don’t believe in finding love anymore.
Even when my peers and I were using dating apps, no one used them with the same expectation and urgency as Sarah, Wan Ting, or Daniel. That’s crucially because loneliness looks different across generations. Gen Zs, for all our gripes with singlehood, still have work, school, and a fairly busy social life to tide us through the pain. For Gen Xs with a shrunken social circle and impending retirement, living and dying alone is a far bigger threat.
Dating apps aren’t a perfect solution. The experience can suck across generations. But it’s allowed our older singles to confront their loneliness—to take control and actually do something about it.
