teamed it with dark jeans that look incredibly expensive – slim fit and artfully distressed with the hems tucked into a pair of chunky black boots. The overall impression is of one of wealth, style and unabashed ostentatiousness. Olly is clearly the kind of man who wants to be noticed. He turns to me as we arrive at the lift and I smile innocently, as if I haven’t just been giving him an appreciative once-over.
‘The office is on the sixth floor, I’m afraid,’ he says, reaching for the button.
‘No problem!’
The lift doors open and we step inside. I know we’ll have small talk in the lift and I brace myself for him to ask me a similar question to Gina, about how far I’ve had to come to get here. As he presses the button for the sixth floor, I gear myself up to lie about being a chartered surveyor on Staten Island.
‘So…’ Olly says. ‘Have you used a dating agency before?’
‘Oh!’ I comment, a little shocked but mostly just hugely relieved to not have to lie just yet. ‘Actually no, never.’
‘Ah, I see.’ He nods. ‘So how did you hear about us?’
Oh, you know, I just Google-stalked you because you’re my boss’ number one competitor, I think.
‘I read about you in Time magazine,’ I tell him, which is technically true. I did read a gushing article in Time magazine last night hailing Olly as a ‘New York matchmaking God’. The interviewer sounded smitten, describing him as ‘the best thing to happen to Manhattan’s dating scene for years’.
‘Ah yes, they gave us some good coverage,’ Olly recalls, flashing me with another dazzling smile.
With his sparkly crinkly eyes and natural charisma, I can see why the interviewer at Time would have fallen for his charm. He’s incredibly handsome. Even though he’s much older than the kind of guy I’d usually find attractive, he has the type of face that ages well. His bone structure is strong and his features are incredibly symmetrical. The thing is, he knows it. I can just tell by the way he’s smiling at me, holding eye contact, expecting me to turn to mush. And maybe under normal circumstances, I would, but I feel mentally detached. I’m not my usual relaxed self, I’m in undercover spy mode and instead of getting too swept up in the charm of a good-looking guy, I’m trying to stay focused on making observations and mental notes instead.
The lift arrives at the sixth floor, the doors parting to reveal an open-plan office with a dozen or so trendy-looking staff sitting behind the giant screens of state-of-the-art Mac computers. Their eyes flick up at me and Olly as we pass and I can feel them watching us as we make our way towards Olly’s private office, which is enclosed in polished glass walls emblazoned with the Elite Love Match logo.
‘After you,’ he says, holding open the door for me.
‘Thanks,’ I reply, smiling shyly as I slip past him.
His office is slick and impressive, with a wide desk, flanked by two wide leather desk chairs. It’s immaculately tidy and clutter-free, a giant Mac computer taking centre stage next to a stainless-steel desk lamp.
‘Please, take a seat.’ Olly gestures towards the seat opposite his desk. ‘Can I get you anything? Water, tea, coffee?’
‘Oh, water would be great,’ I reply as I sit delicately down, willing the zip on my skirt to stay in place.
‘Still or sparkling?’ he asks as he sits down opposite.
‘Sparkling, please.’
‘No problem.’
Olly picks up his phone, presses a speed-dial button and makes a call to someone I assume is his assistant, asking her to bring two sparkling waters.
‘So…’ he says as he hangs up, fixing his deep brown eyes on me. ‘What’s brought you to Elite Love Match today?’
He leans back in his chair and regards me with a gentle patient expression. I can’t quite tell if he’s putting on an attentive ‘listening face’ as part of his sales routine or if he really is genuinely interested.
‘Well, I’ve been single for a while now and I just don’t seem to have any luck with men,’ I tell him and so far, I’m being 100 per cent honest. Why lie? This bit is all true, I do have terrible luck with guys.
‘What do you mean you don’t have any luck,’ Olly asks, tilting his head to the side.
‘Umm…’ I cross and re-cross my legs and glance at the stack of business cards in a neat metal holder on his desk, next to a matching desk tidy. It feels weird to be having such an intimate conversation in such a corporate environment. I think back to the last few guys I’ve dated. I met one guy through my barmaid job at The Eagle – a trainee architect called James. He was probably the only straight man in the bar one Friday night and we immediately caught each other’s eye. He was gorgeous and at first, everything seemed to be going brilliantly. We had a couple of amazing dates, sharing everything from our favourite books and films to childhood memories and our hopes and dreams. Then after our third date, which culminated with us sleeping together, he stopped texting and that was that. I never heard from him again. He ghosted me. It took me months to stop worrying that I was terrible in bed and just accept that he was an asshole. And then before him, there was Mike (the guy I called Matt the entire time we were dating). He was sweet but unlike James, we just didn’t connect. Conversation was always awkward and clunky, no matter how much time we spent together. I kept hoping we might relax into each other’s company, but it never quite happened.
Sometimes, late at night, Olly’s question about why I don’t have any luck with men has stalked my mind, replaying over and over as I try to get to the bottom of it. Why don’t I have any luck with them? Is it possible for a person to be consistently unlucky in love, never quite meeting the right person just because fate hasn’t been on their side, or is there something about me that’s causing these dating disasters? The only theory I’ve come up with is that on some level, I just haven’t felt ready for a serious relationship even though everyone else seems to want to be in one.
My relationship role models are my parents and they met when my mum was 30 and my dad was 33. My mum used to tell me when I was a kid that she was so glad she ‘got to know herself before getting to know someone else’. She was perpetually single until she met my dad, but she’d done a ton of stuff, like charity work, studying and travelling around the world. My dad had travelled a lot too and even though he’d had girlfriends, he’d never been able to stick at a relationship, until he found my mum and decided she was the one, leading him to settle down in Cornwall. I think part of the reason I’ve pretty much always been single is because I took my mum’s advice on board – I wanted to make sure I got to know myself before finding someone else. I’ve always thrown myself into non-love-related activities. I was a bit of a swot at school because back then I was focused on getting good grades so I could get into a US university. Then at university, I threw myself into my photography studies. I focused on having a good social life and I made the most of all the extra-curricular activities on offer. I knew I was paying way more in tuition than I’d be paying for university in the UK so I wanted to make sure I got the most out of it. With all that going on, I didn’t have much time for love. And then when I graduated and moved to New York, I became focused on trying to become a professional photographer and getting ahead. All my life, love has taken the back seat. It’s felt less important than achieving my goals and getting to know myself. Except, I feel like I know myself prettywell these days and annoyingly, I still can’t seem to find love. But I guess you can’t force these things.
‘I suppose I haven’t met anyone for a while who I have a genuine spark with, you know, where it just feels effortless. The kind of spark that you just can’t ignore, when you’re just drawn to someone and neither of you can stop thinking about each other,’ I tell him, looking into his eyes and feeling that fluttery feeling in my stomach again. ‘I suppose I just want that.’
Olly nods understandingly. Without realising it, I’ve somehow opened up to him more than I’ve opened up to anyone for