Ok, so I have to confess the title of this post is particularly misleading. I haven’t suddenly become a fearless flirt but I did go on a ‘fearless flirting tour’.

The ‘fearless flirting tour‘ is run by a woman named Jean. Jean is a social anthropologist.

Jean runs these tours for those who like me for whatever reason have a mental block when it comes to approaching the potential objects of their desire.

Jean said herself that most of the people who go on her tours are generally confident and do fine in other areas of their lives but for some reason  they can’t seem to get rid of that little devil on their back, internal fear when they see someone they like.

She explained that this all comes down to the fear of rejection. Jean disputes that we should even fear rejection as she questions the fact that we allow complete strangers to have that amount of power over us and allow our self worth to be dictated by how they may or may not react to us.

I think Jean may be right but sadly if it was as simple as telling yourself you shouldn’t be afraid and then magically you were ready to conquer the world, I’d be Prime Minister by now!

The tour group met at the National Portrait Gallery, there were 10 of us altogether including 1 solitary male, there were another 2 guys who were supposed to join us but clearly it proved too much for them. We assembled in the gallery and listened to Jean pontificate about why people fear rejection and then she set us to our first task.

In pairs we were to ask a question using one of the paintings as a prop. Although we were assigned to pick someone of the group we’d never spoken to before this did feel safe as I knew that everyone else was there for the same reason as me. But I understand that this was a way to ease us into starting conversations with complete strangers.

The next task was to walk around the gallery and make eye contact and smile at 3 strangers. This one I found all too easy. As you may have read during my previous self challenge it’s become second nature to smile at strangers, however the most difficult part was finding strangers who were willing to make eye contact with me (albeit accidentally). I find, especially in London people are so acclimated to not bothering other people they actively do not lock eyes with anyone so it did take a while to complete this task. After finding strangers to smile at we were to meet outside the gallery. This is where I ran into trouble, I somehow managed to get turned around and ended up wandering into a part of the gallery I didn’t recognise. After a frantic 10 minutes in which I nearly wore my Mary Jane heels down to the sole running up and down stairs I was eventually reunited with my group.

The next task was to walk towards New Road and along the way ask 3 strangers for directions, but that wasn’t all, Jean tasked us with asking a follow up question and not just running away after shouting a hurried thank you over our shoulders to their retreating backs as would be normal in this situation. I concede I found this more difficult, directions I can ask for, asking a follow up question of a completely random stranger with no context in my head, not so simple. I asked 2 people for directions (so I didn’t even get up to 3) and once they replied my mind went blank and I couldn’t think of one solitary question to ask at the time. A complete failure, but I didn’t have long to beat myself up as I had to get back to the group.

Next, Jean took us to Tesco, she explained that similarly to using the paintings in the gallery as a prop we could also use food in the supermarket as a talking point. By asking questions like, have you tried this? Or What would you recommend? We make the other person feel special that we have sought their opinion. I did find this a novel idea as usually when I go food shopping, short of asking someone to reach for something from the top shelf (the perils of being only 5’) I don’t usually have much cause to make conversation with strangers. Having said that I do think it would be the ultimate meet-cute though. When asked “So how did you two meet?” We’d roll our eyes, smile conspiratorially at the memory and then joke “Our eyes met over the legumes in Tesco, and I asked him how big his courgette was…”

Unfortunately I didn’t fare much better in this task than the ‘asking for directions one’ in fact I was worse. In my defence the odds were a stacked against me. Aside from Tesco’s staff the majority of the people in the store were on the tour with me. However I did manage to strike up a conversation with 3 lovely women while I was lurking in the wine aisle (where else would I be?). I managed to ask about a rather conspicuous bottle of Rioja as I had never seen white Rioja before. Upon leaving Tesco and feeling frustrated at my continued failure I resolved that I must try harder.

For our final act we continued on to Covent Garden and were set the task of approaching anyone and talking about anything and then we would reassemble in a nearby pub. For those who have never been to Covent Garden let me set the scene. Imagine a market square lined with cobbled streets, bustling with people and street performers. Covent Garden is essentially tourist central meaning there were plenty of victims *ahem* I mean people to practice on. What was nice about this task is that we were allowed to pair up and immediately as we were dispatched OS dragged me over to two very young looking boys who upon further grilling revealed they were visiting from France. Unfortunately due to language barriers the conversation didn’t really take off.

As we were searching for our next victims a light bulb flashed above my head. I told OS to follow my lead as I spied a decent looking man in the distance. He was looking back behind us as if searching for someone and for a moment I faltered as I was concerned he was looking for his girlfriend (it would be just my luck) but alas when he was joined it was by a slightly older gentleman.

Fantastic! I could commence with the plan. I meandered over and after adopting an innocent expression I started. “My friend and I are looking for somewhere to have dinner, can you recommend somewhere?” The older of the two promptly put his arm round me. Success! Turns out they weren’t from London and couldn’t recommend anywhere, but they were going for dinner themselves and they invited us along. Unfortunately we had to reconvene with the tour group otherwise who knows how it would have turned out. After a short and amusing conversation we swapped cards.

So what did I learn from this experience?

1) You can in fact talk to anyone about anything it really doesn’t matter what you’re saying in most cases people will respond.

2) If the person doesn’t respond the problem is theirs and not yours, best case scenario they are merely having a bad day or worst case they are an inhuman devil who has absolutely no compassion and if that is the case would you want them to respond to you anyway?

3) When I need to be, I can be brave and inventive but I think I do my best work when I have a wing woman along for the ride.

And who knows, hopefully one day I’ll get round to bonding over the legumes at Tesco.