Mar 11 2025.
views 66Online dating is a paradox of modern romance - equal parts thrilling and bewildering. For every promising connection, there’s a cautionary tale lurking in the background. The swipe-right culture has introduced a new wave of possibilities, but it has also made red flags easier to miss in the rush to find something meaningful.
Here, we explore firsthand experiences of dating app disasters and the subtle (and not-so-subtle) warning signs to recognize before it’s too late.
Yasodhara: “Coming out of a 12-year marriage, and domestic abuse, which left me feeling so much less than myself and unsure of my own worth, I decided to go on what I like to call a Tinder rampage. What this meant was saying yes to 2 weeks of dates, every night, without prior judgment on my part of what my 'type' was. This was purely for me an exercise in 'getting back' into the world.
It was glorious. For the most part. Such interesting people, most of them not for me romantically, but still great people. I had my own rules for me. Nothing physical with any of my dates till the 2 weeks were over, and that suited me well as I was looking to only expand my horizons.”
Ruwan: “I had been out of the dating game for years, focused on my career and assuming love would just happen when the time was right. A friend convinced me to give dating apps a shot, and I went in with zero expectations. What I didn’t anticipate was how exhausting it would be. The constant messaging, the weird conversations, and the sheer number of people who seemed great online but totally different in person.”
Meera: “I had never tried dating apps before, but after my best friend met her fiancé on one, I figured - why not? My first few experiences were a mix of awkward, funny, and frustrating. One guy showed up wearing a Bluetooth headset the entire date. Another asked if I believed in soulmates before we even ordered drinks.”
Some matches begin with an intoxicating level of attention - messages flooding in, grand declarations of admiration, and talk of a future together before you’ve even had a proper conversation. It feels like a whirlwind romance, but more often than not, love-bombing is a precursor to control.
Ayesha: “He messaged me constantly, telling me I was unlike anyone he’d ever met. Within a week, he wanted me to meet his family. At first, it felt flattering - until his tone changed. When I didn’t reply fast enough, his adoration turned into accusations of ignoring him.”
Ruwan: “One guy told me he was in love with me after three days. When I laughed it off, he got defensive and said I obviously wasn’t emotionally mature enough to understand deep connections. Blocked.”
Red Flag: True connection unfolds naturally. If someone is overwhelming you with affection right away, take a step back and assess whether it’s genuine - or a ploy to fast-track emotional dependence.
Some people prefer to take their time opening up, and that’s fair. But when someone dodges basic questions or keeps the details of their life under lock and key, it’s worth questioning why.
Yasodhara: “There was the guy who acted like James Bond, never sharing anything about himself, expecting me to be in awe of him. I later realized that the entire date he never moved once, he was seated when I arrived and stayed seated when I left. Weird.”
Meera: “I asked him what he did for a living, and he just smirked and said, 'I do well for myself.' Okay... but what do you actually do?”
Ayesha: “Three dates in and I still didn’t know his last name. Enough said.”
Red Flag: A little intrigue is exciting, but a complete lack of transparency is not. If your date refuses to share even the smallest details about their life, consider whether they have something to hide.
A relationship should be built on trust, not constant validation. If someone is already showing signs of possessiveness before the second date, it’s a preview of what’s to come.
Meera: “He saw I was online on WhatsApp and texted me, ‘Who are you talking to?’ after we had just one coffee date. Immediate no.”
Nadun: “I went on a first date with someone who seemed nice enough, but when I mentioned I had dinner plans with a friend the next night, her entire demeanour changed. She actually asked me, ‘So you’d rather see a friend than go on a second date with me?’ That was all I needed to know.”
Red Flag: Early-stage jealousy can quickly morph into controlling behaviour. If someone is questioning your decisions or trying to monopolize your time immediately, that’s a signal to walk away.
There’s nothing wrong with appreciating the finer things in life. But when a date spends the evening flaunting their wealth or possessions, it often signals a need for validation rather than a desire for connection.
Ayesha: “He kept dropping names of fancy restaurants, hotels, and brands he supposedly owned, but when I asked basic questions about them, he got cagey. I think he Googled half those things before our date.”
Yasodhara: “There was the guy who told me that I was the most intelligent woman he had met, which came off more as an insult to women than a compliment to me, who also spent all of his time giving me detailed descriptions of everything designer that he owned. Instant puke.”
Red Flag: If someone is more interested in impressing you with their material worth than getting to know you, chances are they’re compensating for something deeper.
Sometimes, the most promising matches - the ones who check all the right boxes - fail to spark anything meaningful.
Yasodhara: “There were a couple of great dates. One so good-looking, and so incredibly well dressed that he looked like he was from a magazine. But so dull. And that I can’t work with. There was another who had all the personality, pizzazz and humour that I needed, just not the chemistry. And we are still close friends to this day.”
Lesson Learned: Attraction goes beyond credentials or aesthetics. If you find yourself trying to force a spark, it’s likely not meant to be.
Dating apps offer a fascinating cross-section of humanity -the brilliant, the bizarre, and everything in between. While there’s value in stepping outside your comfort zone, it’s equally important to stay attuned to your instincts and establish firm boundaries.
As Yasodhara wisely puts it: “What the rampage taught me was that there are so many different sorts of people out there, and we are all just trying to find somewhere to belong. A sense of home. And the people who seem great on paper, sometimes just aren’t the right fit. And the people who don’t seem great on paper are sometimes the ones we have chemistry and alignment with.
So all we can do is give people a chance with an open heart. Draw boundaries for ourselves and be honest with ourselves about how we feel. The rest will just make for great stories to share with the girls.”
At the end of the day, online dating is an adventure. The key is to enjoy the journey while keeping an eye out for the signs that something isn’t quite right. Because while bad dates make for great stories, your safety and peace of mind should always come first.
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