#UNTOLD | Rejection, Relationships & Shalini Singh: The woman who refused to give up on love

For a long time, Shalini Singh simply stared at the laptop.

She knew what came next. She had rehearsed this moment in her head a hundred times. She shut the lid, stood up and walked to the other end of the room. A few moments later, she was back at the desk. She opened the laptop again.

Nothing had changed. Neither had the decision waiting for her.

She got up again. Walked to the fridge. Took a long swig of cold water. And waited, hoping the silence would do what she couldn't.

It didn't. She returned to the chair. Opened the laptop. Read the screen again. Maybe another month. Maybe one more attempt. Maybe...No. She had run out of maybes.

Five years earlier, Singh had walked away from a successful communications career to build something she believed the world desperately needed. It wasn't just another platform. It was born from a question that had followed her for most of her adult life: Why do people spend so much time choosing careers and so little time understanding the person they choose to spend their lives with?

The journey had been far harder than she had imagined. Cofounders had come and gone. The business had stumbled through setbacks that tested not just the company, but her own belief in it. By 2024, shutting it down no longer felt unthinkable. It felt inevitable.

She looked at the screen. Then looked away. Then back again. She couldn't do it. She couldn't continue either. Somewhere between those two thoughts, she broke.

"I was bawling," she recalls.

It wasn't just the company she was grieving. It was the possibility that the world had been right all along. That the idea she had spent years fighting for wasn't worth fighting for. That perhaps she had mistaken conviction for stubbornness.

As the tears broke through, another memory arrived. A drawing room. A tray of tea. Polite smiles. Families who had come to "see the girl." The ritual was almost always the same. Conversations drifted through education, family and careers. Everyone smiled. Everyone was courteous. Everyone behaved as though the decision would take time.

It rarely did.

A few hours later, the phone would ring. They had decided not to take the conversation forward. Sometimes the reason was her complexion. Later, it became her age. The explanation changed. The verdict never did. She wasn't the one.

Most people carry rejection as a wound. Singh carried it as a question.

Why should the colour of someone's skin decide whether they deserved companionship?

Why were strangers expected to judge compatibility after a single meeting?

Why did everyone seem comfortable making one of life's biggest decisions with so little understanding of the person sitting across from them?

Those questions refused to leave. Over the years, she found pieces of the answer in the most unexpected places.

One of the first places she found them was among four-year-olds. Children don't know how to pretend. They laugh without restraint, cry without embarrassment, fight over a toy and forgive five minutes later. As a kindergarten teacher, Singh found herself watching more than teaching. She observed how naturally children expressed what they felt. An argument over a toy ended in tears and, minutes later, laughter. Apologies came easily. So did forgiveness.

Somewhere along the way, another question began to bother her: When do we lose this honesty?

How Shalini Singh's Personal Journey Became the Foundation of ‘andwemet’?

Professionally, Singh moved into the world of communications, helping organisations tell better stories.

Yet outside boardrooms and client meetings, she noticed something that fascinated her even more. People who communicated brilliantly at work often struggled to communicate with the people they loved. Education, achievement and successful careers made them better professionals. But they didn't necessarily make them better partners.

The more she observed, the larger the question became. She was no longer asking why she had been rejected. She was asking why people made one of the biggest decisions of their lives with so little understanding of themselves.

The answer, she increasingly believed, wasn't helping people find better partners. It was helping them know themselves before choosing one.

The company still didn't exist. The idea already did. Turning that idea into a company would take much longer than she imagined. It took years before Singh found the courage to act on those questions. Not because she lacked conviction. She wasn't ready.

The questions she had carried since her twenties refused to disappear, but neither did life. She built a successful communications career, lived overseas, returned to India and eventually started her own communications consultancy. Yet somewhere in the background, she kept returning to the same puzzle.

What makes a relationship work? More importantly, what makes one fail?

The answers didn't come as revelations. They accumulated quietly over the years. And slowly, Singh realised that the rejection she had once experienced because of her complexion had merely been the beginning of a much larger education. The deeper she looked, the more fundamental the questions became.

Why marry at all?

What did she actually want from a partner?

Was marriage the goal, or was companionship?

Those questions became deeply personal when she entered her mid-thirties. For years, she had consciously stayed away from relationships while trying to understand herself. Then, after completing her first half marathon at 36, feeling healthier and happier than ever, she told her mother she was finally ready to meet someone.

The response surprised her. "You want to find someone at this age?"

For Singh, 36 felt like the right time. To many around her, it already felt late.

That moment changed the way she looked at India. She became curious about the invisible deadline society had quietly imposed on women. Somewhere around 28, the conversations changed. By 30, the pressure became relentless. Marriage was no longer treated as a choice. It became a countdown.

Instead of accepting that reality, she began studying it. She spoke to singles. She observed how they searched for partners. She explored matrimonial platforms and dating apps. The more she watched, the clearer one thing became. People weren't necessarily making bad choices. Many were making rushed ones. Pressure was deciding before clarity ever had a chance.

Then life surprised her. She met the man who would become her partner. Not when she was searching desperately. Not when society thought she should. But when she finally understood herself. She was 38.

Looking back, she believes meeting him earlier might actually have been the wrong time. She wasn't ready then. She hadn't yet done the inner work that relationships quietly demand. Both of them arrived with different personalities, different life experiences and different emotional baggage. What made the relationship work wasn't similarity. It was self-awareness. She didn't know it then, but that realisation would eventually become the foundation of everything she built.

But before she could build the company right, she would build it wrong.

What all did it cost Shalini Singh to Build the Wrong Startup First

By the time Singh finally decided to build, she wasn't a twenty-something founder chasing the next startup idea. She was in her mid-forties. She had already built a successful career, run her own communications consultancy and found a partner. Entrepreneurship wasn't the obvious next chapter. If anything, it looked like the unnecessary one. Almost everyone around her thought so. Everybody said no.

Why leave a comfortable career?

Why step into a category where even established dating apps struggled to make money?

Why build something most people didn't even think was a business?

Singh heard every argument. Then she ignored them.

In the latter half of 2019, ‘andwemet’ was born. Singh wasn't trying to build another dating app or another matrimonial platform. She wanted to create something that encouraged people to slow down, ask better questions and approach relationships with greater clarity than urgency.

The conviction was right. The execution wasn't. "I was emotional," she says. She wanted the venture so desperately that she stopped trusting herself. Instead, she trusted everyone else. The result was a series of decisions that nearly destroyed the company before it had a chance to find its footing. She chose the wrong cofounders. Not once. Not twice. Three times.

Looking back, the irony isn't lost on her. For years, she had urged people to understand themselves before choosing a life partner. Now she was making the same mistake herself. Not in love but in business.

"I was making the same mistakes anybody would make while looking for a partner," she says, adding that she was looking for a cofounder and ended up meeting the wrong people.

The price was brutal. Every wrong decision delayed the company she had imagined. Money disappeared. Time disappeared. Confidence disappeared. "It cost me a lot, both emotionally and financially," she says. Five years after taking the leap, the company still wasn't the one she had set out to build. For the first time, giving up felt easier than carrying on.

She didn't know it yet. Her hardest lesson as a founder was still waiting for her.

Why andwemet Focuses on Relationship Guidance, Not Just Matchmaking?

The answer didn't arrive overnight. But when it did, it was unmistakable.

If she was going to fail again, it would be because she had tried something new. Not because she had repeated an old mistake.

"I cannot make the same mistakes I made earlier," she told herself.

One decision followed another. She stopped trying to rescue everyone. She stopped saying yes to every idea. She stopped confusing empathy with strategy. For years, she had been trying to build an ethical service without building a sustainable business. This time, the two had to coexist. One without the other wouldn't survive. She wasn't entirely alone. One member of the team had stayed through the chaos. When Singh asked him whether they should give the company one last shot, his answer came without hesitation. "Haan, karte hain (yes, let's do it)."

Sometimes, that's all a founder needs. Not certainty. Just one person willing to believe again.

The comeback didn't begin with a polished app or a high-profile launch. It began with a WhatsApp community and not some fancy technology or elaborate product roadmap. Just conversations.

The response surprised her. People joined. Then they stayed. Soon, they started paying. For the first time since launching the company, the business wasn't surviving on hope alone. Customers were willing to pay for what she had spent years trying to build. But something else surprised her even more. People weren't simply looking for introductions. They were looking for guidance.

How do I know if I'm ready for a relationship?

How do I communicate difficult conversations?

How do I recover from divorce?

How do I navigate dating in my thirties?

The company was quietly teaching Singh what it actually wanted to become. The insight was deceptively simple. People weren't struggling because they lacked options. They were struggling because nobody had taught them how to make better relationship decisions.

That insight reshaped everything.

Today, andwemet is an invite-only community. Not because Singh wants it to feel exclusive. Because she wants it to feel intentional. Years of conversations had convinced her that serious relationships begin with serious intent. The invitation process acts as a filter, creating what she calls a sense of "sanity" for people genuinely looking for long-term companionship rather than endless swiping or casual interactions.

Another lesson emerged from listening.

When the company first started, it welcomed people aged 25 and above. Then women in their mid-twenties began telling her something she hadn't expected. They weren't ready. They wanted time to understand themselves before committing to someone else. Their honesty forced Singh to rethink one of the company's earliest assumptions. The age threshold quietly moved to 28. Not because 28 is a magic number. Because hundreds of conversations suggested that intention often changes around then.

The insight extended well beyond one product decision. Across urban India, people are marrying later than previous generations. Careers are taking longer to build. More people are navigating break-ups, divorces and second chances. Yet much of the relationship industry still treats them as one homogeneous market.

Singh believes they aren't. Whether that bet ultimately proves right remains to be seen. But if it does, it could reshape how relationship platforms think about one of India's fastest-evolving demographics. Every important product decision now follows the same principle. Listen first. Build later.

The philosophy extends beyond matchmaking.

Today, the company offers relationship guidance, dating guidance, intimate online meet-ups and a programme called Wedding Gift for couples preparing for married life. The common thread isn't marriage. It's helping people make one of life's biggest decisions with greater awareness than the generations before them.

What was the Bigger Mission Behind Shalini Singh's Startup?

The company has also remained bootstrapped. Not because Singh is against raising capital. She simply believes the business has to earn that right first. Early conversations with investors convinced her that many still struggle to see relationship guidance as a venture-scale category. Rather than chase funding before the model was ready, she chose to chase traction. Funding, she believes, will come later. After the business matures, after the services deepen, and after the company expands globally.

Ask Singh today what success looks like, and she doesn't begin with revenue, valuations or scale. She begins with people. The woman who was once rejected because of her complexion now spends her days helping strangers believe they deserve love, companionship and a second chance.

Years of listening have brought her to a conclusion that sounds almost embarrassingly simple. India prepares people for almost everything except relationships. We teach children how to score marks. We prepare them for competitive exams, college admissions and careers. We coach them to become engineers, doctors, consultants and entrepreneurs. But almost nobody teaches them how to understand themselves or communicate honestly or resolve conflict or choose a life partner with intention.

That, she believes, is why so many accomplished professionals struggle in their personal lives. Success at work doesn't automatically translate into emotional intelligence. A brilliant résumé cannot compensate for poor communication, a lack of self-awareness or the inability to see the world from another person's perspective.

The advice she gives singles today is remarkably similar to the advice she would give any founder. Don't rush. Don't choose because everyone else thinks it's time. Don't ignore your instincts. And above all, don't repeat the same mistakes.

Those lessons were earned the hard way. As a young woman, she learnt not to let strangers' judgments define her. As a founder, she learnt that conviction without self-awareness can be painfully expensive. The two journeys were separated by decades but they were connected by the same lesson: Know yourself first. Everything else comes later.

Every night before going to bed, Singh still asks herself the same question. What more can we do for these people? Perhaps that's why she no longer thinks of andwemet as a startup. She thinks of it as a lifelong mission.

Years ago, she sat frozen in front of a laptop, trying to decide whether it was finally time to shut the company down.

Today, she still ends many days in front of a laptop. Only now she isn't looking for a way out. She's looking for a way forward. Not for the next quarter but for the next generation. One conversation. One relationship. One lesson. One brick at a time.