Woman Reflects On Her Decade-long Singlehood And Navigates The Challenges Of Dating Again In London

At the start of 2025, I found myself facing a rather surprising realization: a decade of being single had caught up with me.

It wasn’t just a passing thought but a milestone that felt much bigger than I had imagined.

With New Year’s in full swing, I made a resolution to finally be proactive in my dating life.

Like many, my goals were to find love and try to meet someone special.

So, I dusted off my Bumble profile, swiped with renewed purpose, and even set up a first date. I was on fire… until the excitement fizzled into crippling anxiety.

Suddenly, I was drafting an apology to cancel on him, only to delete my account before he could even respond.

The Struggles of Getting Back Into Dating

There’s no shortage of advice about dating after a long relationship, but I quickly discovered that dating after being single for a long time is a whole different beast.

It’s kind of like running a marathon with no training—it leaves you breathless.

Sure, apps make it easier to dive back in, but putting yourself out there in real life feels much harder than it seems on the screen.

So, I decided to try something a little different: I asked an Instagram dating expert out on a mock date, hoping he could give me feedback on my skills, from banter to eye contact.

Little did I know, that decision would lead me to a date I won’t soon forget.

Meeting Tom Stroud at a Glamorous Soho Bar

That’s how I found myself heading to a posh bar in Soho on a rainy February evening to meet Tom Stroud.

Tom, a 40-year-old former reality TV star-turned-relationship expert, was already seated in a cozy booth.

You might remember him from the British version of Love Is Blind UK, where he famously proposed to Maria Benkh sight unseen before their relationship hit some rocky waters.

Since then, Tom has been all about exploring modern relationships and male behavior, building a huge following with his social media content.

He even works with Bumble as one of their UK ambassadors and co-hosts a podcast, Why Do Men?, diving into the complexities of love and romance in 2025.

A Nervous Start But an Unforgettable Date

As I walked into the venue, I found myself rehearsing a clever opener (“At least there was no way you could be a catfish!”) and mentally preparing for the critique I was sure was coming.

But then, of course, the inevitable happened. In my nervousness, I knocked over the vase on our table.

Tom, thankfully, wasn’t bothered and found it endearing. It was a great icebreaker, and before long, we were deep into conversation.

We chatted about everything—his recent trip to Cape Town, his relationship with Maria, my experiences growing up in New Delhi, and everything in between.

It didn’t take long for me to forget we were just pretending to be on a date.

Getting Real About My Nerves and Clumsiness

After the 45-minute mock date, Tom offered some surprising yet helpful feedback.

He pointed out that while my nervousness was clear, it was also something he found charming.

Still, he suggested I try to work through those nerves before a real first date so I wouldn’t come off too chaotic.

The key takeaway? “A first date isn’t about impressing someone else; it’s about being authentic to yourself,” he told me.

It was a wake-up call after years of trying to mold myself into the ‘cool girl’ ideal.

It reminded me that my needs and authenticity mattered just as much as those of any potential partner.

The First Date That Doesn’t Have to Be Perfect

Tom also shared a practical piece of advice I could immediately use: skip the dinner on a first date.

Instead, opt for a coffee and a walk. It’s casual, brief, and gives you an easy out if things don’t click.

I nodded, feeling a sense of relief at how simple and non-pressured that sounded.

A 20-minute coffee could turn into something much longer if the connection is right, and no one needs to feel trapped in a long, drawn-out dinner.

My pride in the moment was a little surprising too—Tom not only reordered his Old Fashioned but suggested we share two starters.

If only this were a real date, I thought.

The Art of Flirting and Being Present

As we continued, Tom gave me some honest feedback on my flirting style.

Apparently, I had been relying too much on banter and fun, and not enough on showing direct attraction.

He also mentioned how I tended to mentally map out conversations before they fully unfolded, missing out on some natural moments of silence or pauses.

He recommended embracing those lulls and letting things unfold organically.

It was eye-opening advice, and I could feel myself becoming more comfortable as the date went on.

Intentional Dating and Avoiding the Pitfalls

We also discussed the importance of being clear about intentions on a first date.

According to Tom, it’s essential to ask questions like, “What are you looking for?” and to answer honestly.

In fact, he believes being upfront is key to avoiding misunderstandings down the line.

Bumble data has shown that most women want a partner who brings emotional stability to the table.

Tom echoed this, adding that intentional dating should involve asking the hard questions early on.

At the same time, there are topics to avoid—finances and exes should definitely be off-limits on a first date, he suggested.

Taking the Pressure Off and Enjoying the Moment

By the end of the evening, I found myself reflecting on the fun I’d had, even though it was just a mock date.

It reminded me of the importance of enjoying the moment rather than worrying about ticking boxes or trying to be someone I’m not.

Dating, like relationships, should ultimately be about having fun and being your most authentic self.

As I drained my glass, Tom nodded approvingly, and I couldn’t help but smile.

Despite the awkward start and nervous missteps, this mock date had taught me more about myself than I ever expected.

Expert Dating Advice for the Next First Date

After my experience with Tom, I sought additional dating wisdom from experts like Paul Brunson, a star from Married at First Sight, and TikTok dating coach Jacob Lucas.

Their advice focused on avoiding common first date mistakes, such as talking too much about yourself or bringing negativity into the conversation.

They also emphasized the importance of body language and creating a relaxed atmosphere to help take the edge off the date.

Ultimately, as I reflected on everything I had learned, I realized that first dates, and relationships in general, are less about following a set of rules and more about embracing who you truly are.

That was the most important takeaway from my not-so-real date with Tom Stroud—and the one I’m determined to carry forward as I dive back into the world of dating.