“Will you be my friend?” Inside my terrifying experiment to connect with New Yorkers

I haven’t always been good at making new friends. In fact, heading into my 40s a few years ago, I realised that I was lonely – and I made a huge effort to turn things around. Doing so felt vulnerable; but it was nothing next to the 36 hours I spent in New York City last month, asking strangers to be my friend. 

I’m currently in the process of moving from London to the East Coast, along with my co-founder and wife, Radha Vyas. The move is work-motivated; I’ll be overseeing Flash Pack’s America expansion. But if I want to be happy there, I’ll have to become even more proactive about meeting and making friends. 

It’s no mean feat. The Big Apple is regularly voted one of the unfriendliest cities in the world; a truth that hits hard for the 57% of New Yorkers who feel isolated and alone. Made worse by Covid, this loneliness epidemic is not just unfortunate – it’s a health crisis equivalent to smoking 15 cigarettes a day.

Watch: “Will you be my friend?” social experiment

So, I decided to carry out a social experiment. What would it be like to put myself out there, and simply ask strangers, “will you be my friend?” And to do so in some of Manhattan’s busiest and most aloof places; from Union Square and Grand Central Station to Line 6 on the NYC Subway? Armed with a hidden TV crew and all the courage I could muster, I set out to see. 

The first thing I noticed is that I was absolutely terrified. My heart was pounding in my ears as I surveyed a sea of commuters spilling across Grand Central, wondering whom best to approach. Things got even tougher when I headed out onto the streets – where people actively avoided me – and then onto the subway, where I addressed packed carriages of New Yorkers on Lines 4, 5 and 6.

My public request for friends left me feeling horribly exposed

There is something about speaking up in front of a captive audience of commuters that feels horribly exposing. No-one asks the question “will you be my friend?” beyond about the age of 5, so I really had to push myself to do it. Mostly, I was met by silence and disbelief. Looking around, I could see commuters snickering or shaking their heads. One woman was disgusted by my request; she told me it was “genuinely off-putting”. Other people avoided eye contact or moved away as quickly as they could. Their embarrassment was palpable. 

But then, I had an unexpected breakthrough. On my final request saying, “will you be my friend?” on the subway, a man responded, “Are you for real?” I confirmed that I was, so we shook hands and then started in on this big conversation about friends and New York City. And the openness of that one interaction prompted others to speak out, too. By the end of the journey, about half a dozen of us in the carriage – all strangers – were chatting together.

These sudden moments of connection cropped up everywhere, from Washington Square Park – where I posed with a sign saying, “will you be my friend?” – to comedy club BATSU!, where I took to the stage in front of a large crowd of strangers, asking them to connect.

I’d gone into the experiment expecting it to be incredibly hard to engage New Yorkers. That was true, to an extent. It was difficult, not to mention toe-curlingly awkward. Ironically, at certain points during the experiment, I’d never felt so alone. But what I wasn’t prepared for was the feeling of exhilaration I had when people did respond and open up.

People avoided eye contact or moved away

Even more amazingly, I did end up making friends. For every encounter where I felt a connection with someone, I invited them to join me for drinks and karaoke at Sing Sing in East Village. In my heart of hearts, I wasn’t expecting anyone to turn up on the night – but five people did. They included one woman from my comedy gig whom I hadn’t even spoken to. But she’d taken a copy of my “friendship résumé” (a joke-style CV I handed out, featuring a rundown on my friendship experience to date) and was intrigued to find out more.

Our impromptu group on that NYC bar night out comprised quite a random group of people. We probably wouldn’t have crossed paths in day-to-day life. And yet we bonded quickly. Conversation flowed, likely because everyone was taking a similar risk in daring to turn up and be open to the concept of new friends. After sharing a few beers together, we hit a karaoke booth and kept singing ‘til the early hours. 

Kirstyn Pearl was one of those who attended the session – and someone whom I now count as a new friend. “NYC can feel like the loneliest place if a Friday night comes along and you don’t have anyone hitting you up to do something, while the entire city is swarming with people and fun things to do,” she says. “With Lee’s vulnerable friendship request, it felt like I would be accepted either way.”

So, there I was, after 36 hours of meeting strangers in NYC – tired, raw and exposed; and with a newfound awareness of what it takes to make new friends in the loneliest city around. What did I learn? Here are a few headline takeaways:

Strangers respond to vulnerability: While the idea of asking “will you be my friend?” is just too cringeworthy for some people, for others, it strikes a chord. Often, New Yorkers stopped in their tracks simply because of it being such a direct, and unusual request. And they commented on my bravery and openness. 

Even more noteworthy is that strangers responded to my vulnerability in kind. I ended up talking to people about all kinds of personal things they were going through, from IVF and sexual identity to the challenges of running a business – all within minutes of meeting them. 

It helps to be direct: Initially, I tried to coat my question with bumbling British politeness. That didn’t work. Why? New Yorkers aren’t so much unfriendly as hyper-busy and focused. So when I cut out the fluff, and just directly asked “will you be my friend?” people often responded instantly. In fact, the one time I was overwhelmed with people was when I was very overt with my ask. When I stood in Washington Square Park with a sign, I could hardly start waving it before people began approaching with a hug or an intro to their dog.

Putting yourself out there feels uncomfortable: At times, it was even excruciating. But looking back, I can barely remember the negative encounters. What sticks with me are the moments where I made real, genuine connections. The New Yorkers who were so interested and moved by my story, they bravely shared their own. I’m not suggesting you wander around NYC with a sign to make friends. But if you risk nothing, you get nothing. Try instead to stretch yourself a bit. Because in making friends, you have to face that fear of rejection –and  trust me, it’s 100% worth it to do so. 

Making new friends is all about confidence: I’m not talking about the kind of confidence where you swagger in thinking you’re awesome and everyone must love you. Instead it’s an inner kind of confidence: the type that comes from doubting yourself and then overcoming that doubt.

Amazingly, I did end up making friends

I used to struggle with confidence issues a lot when I was younger; and I still have moments of self-doubt now. Approaching strangers is by far the most nerve-wracking thing I’ve ever done in my life. So, to be able to confront that awkwardness and push through it felt incredible. It’s a milestone for me. Nothing will feel as uncomfortable as that, but I survived to tell the tale.

It takes a village: The loneliness epidemic we find ourselves in extends beyond the parameters of NYC. And it cannot be solved by one person alone (however often they say, “will you be my friend?”) This reality is why Flash Pack has launched our mission to create one million meaningful friendships. 

You or I, or our colleagues or neighbours – we don’t have to soldier through life alone. As my experiment shows, there are legions of inspiring and funny people out there just waiting to connect. But to do so takes serious effort. We all have to lean in and learn to get vulnerable. And doing so is the best way to break down walls. It’s an adventure, too; an invitation to sit down, share something unique and experience the world in new and powerful ways.

Flash Pack is a group travel company that specialises in small group adventures for solo travellers in their 30s and 40s. Find out more about how we work, and our mission to build a global community of friendships.