Tag Archives: dating challenge series

Blind date: someone I barely knew set me up with a stranger

A lovely woman set me up on a blind date. Yes, my life is like a film now and I’m very grateful for that. How do you reckon the blind date went? For context, I can tell you that I had met this lady precisely once in my life, and during that meeting we’d spoken for less than two hours. She’s a very warm, open person though so our conversation went to fun places really quickly. We commiserated with each other about the terrible state of The Apps these days, and I told her about my dating challenges: why I’m trying to meet men in real life rather than repeatedly bang my head against the brick walls of Feeld and OKC. Three days later, this woman I barely knew texted me: I have a potential date option for you. (Yes I work fast). This magic dating fairy then went on to tell me that the guy in question was funny, sweet, asked questions and that a mutual friend of ours had approved the match. She wanted to know if I was still up for trying out the whole ‘blind date’ idea. I said what you’d expect me to say: Omg seriously?! I am SO IN. Predictions: what do you think?

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Emotional honesty: this guy restored my faith in dating

I can’t tease you any longer, my friends. It was cruel of me to do so in the first place. The fun little trilogy that started with a dating challenge and moved on to me and a hot guy swapping sex stories is just that: a trilogy. It’s not the first chapter in a brand new erotic romance. Fuck it, though, he and I had a lot of fun, and personally I find it fitting (and deeply satisfying for my overall philosophy) that the guy who restored my faith in dating didn’t do so by being the perfect match, but by embarking on our dates with genuine emotional honesty. When I set out on the initial challenge (‘ask out the hot man who works in my shop’) it wasn’t about whether he said ‘yes’, only about whether I was brave enough to ask him in the first place. Likewise, the success of our dates didn’t come down to whether we kicked off a serious relationship, but whether we met as equals with a genuine desire to find out if we matched. The fact that we don’t match is no more than a footnote. The headline is that we found that answer swiftly, respectfully, and while having a fair bit of fun. Shop Man Part 3. Let’s do this.

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“Enough about me, how about you?”

This guy has a really neat dating trick that makes me feel comfortable and relaxed in his company. It’s one which means we get to progress towards knowing each other way faster than I have with most other men in the years since I broke up with my ex. He does it consistently and brilliantly, and each time he does it I’m taken by pleasant surprise. Wanna know what the trick is? It’s easy. Absurdly, ridiculously easy, but quite rare. He asks me questions. That’s it. He asks me about my life, and when I say something interesting he asks a follow-up. If he realises he’s been speaking for too long, and the conversation is becoming a monologue, he says “enough about me. How about you?” That’s it. That’s the trick.

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Dating challenge complete! I chatted up a man in real life

This man has spent the last twelve months greeting me with eager smiles each time I see him. When I walk into the shop, he looks up and sees me then beams a fully radiant grin. I return it with gusto, and he smiles even more brightly. Something about this guy’s warmth makes me want to get to know him better. But something in every fibre of my being recoils at the idea of being bold enough to actually ask him out.

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