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Surely, I’m not qualified to be a matchmaker?!

You’d think getting a job at a dating agency might actually require you to have found love, or at least be good at dating, but apparently not. I’ve been single for three years and I haven’t had a date for six months, yet I’m pretty sure I’m nailing this interview.

‘So, what kind of message would you send Erica?’ Derek asks, handing me a print-out showing a dating profile of a pretty, tanned brunette. Derek is the boss of To the Moon & Back dating agency, although with his nicotine-stained teeth, lurid purple shirt stretching over his giant pot belly and cramped city office, he’s not exactly what I imagine when I think of Cupid.

What kind of message would I sent Erica? When Derek says ‘you’, he doesn’t mean me, as in Polly Wood. He means me pretending to be 34-year-old bachelor Andy Graham, because that’s what my job as a matchmaker would involve. While Andy, and the rest of the busy singletons on the agency’s books, are out earning the big bucks, too busy to trawl internet dating sites looking for love, I’ll be sitting here with Derek, firing off messages on their behalf in the hope of clinching dates. It’s a little morally questionable I suppose, since the women will be chatting to me beforehand, and will no doubt become enamoured with my witty repartee and effortless charm, but to be honest, I haven’t really given the moral side of it much thought. According to Derek, it’s what all dating agencies do, and anyway, ethics somehow stop being so important when you really need cash.

I try to put myself in the mindset of Andy, while thinking up a message for Erica. I only know about him from reading a form he’s supposedly filled in, which Derek gave me to study five minutes earlier. According to the form, Andy is an ex-army officer turned property surveyor. He grew up in a small town in Ohio where his family still reside. His younger brother, aged 31, has already settled down with a wife and three kids, and reading in between the lines, I get the impression that Andy feels he’s beginning to lag behind. He works long hours, reads Second World War history books in his spare time, enjoys visiting aviation museums and likes to play tennis at the weekends. Oh, and he has a penchant for Thai food.

I take a look at Erica’s profile. She’s 32, lives in the Upper East Side and works as a fashion buyer. Her interests are listed as: ‘yoga, fine dining, dinner parties (hosting and attending!), dancing, cocktails with the girls, travelling, tennis, and festivals’. Erica sounds cool. She sounds fun. She seems like a girl about town. And to be perfectly honest, she strikes me as a bit too cool for Andy. I can’t imagine her wanting to visit aviation museums or discuss Second World War history. But for all I know, Andy could have stunningly handsome looks that somehow make up for his yawn-inducing interests. But from what I do know so far, he and Erica hardly seem like a great match. I glance up at Derek, scanning his face for any sign that this might be a trick question, but he simply looks back, keen with anticipation. He doesn’t seem like he’s testing me; he clearly thinks Erica is in Andy’s league, although as far as I can see, the only thing they have in common is tennis.

‘So, what do you think?’ Derek presses me.

‘Erm, I’d keep the opener light. From Erica’s profile, you can tell she’s a breezy, happy kind of person. I’d try to mirror that tone,’ I tell him, biding time while I attempt to think of a witty opener.

‘Good tactic,’ Derek agrees with an encouraging nod.

‘Thanks,’ I reply as I desperately try to come up with an attention-grabbing message. Something that will capture Erica’s attention among the deluge of ‘hey, how r u? x’ type openers she probably receives all the time. But what can I write? What could Andy possibly say that would grab Erica’s attention when their only mutual interest is tennis?! Then suddenly, it hits me. I smile to myself.

‘I’d probably go with something along the lines of “I’m glad to see you’re a tennis player, because I’m going to court you”,’ I tell Derek.

He snorts with laughter. ‘Good one! Cheeky! I think Erica would like that.’

I grin, feeling a flush of pride. ‘Thank you.’

‘Great line! Very good!’ Derek laughs.

‘Thanks. I mean, why play singles when you can play doubles?’ I add, cringing internally. I think I might be taking the tennis puns too far now. Fortunately, Derek laughs again, clearly not adverse to a good sports-themed chat-up line.

‘Indeed!’ he says.

A couple of cars honk loudly outside and for a second, I’m taken out of this surreal alternative reality of pretending to be Andy messaging Erica and it hits me that the real me has probably got this job. In fact, I know I have. I’m 99.99 per cent sure. I can tell by the way Derek is regarding me like a proud father. I can tell in the easy, relaxed way we’ve been chatting the entire interview. We seem to have really hit it off, which is a little disconcerting seeing as I’m, you know, a respectable (okay, at least semi-respectable) person and he’s a middle-aged owner of a slightly shady dating agency. Maybe it’s because I’m British, having grown up in Cornwall before moving to the States when I was 18. Derek said he used to date a Brit, recounting how they went on holiday to Cornwall one summer. He even described it as ‘heavenly’. Or, perhaps we click because we went to the same university. Derek’s barely looked at my CV but he glanced at it for a second as I came in and when he saw that I went to Wittingon Liberal Arts College, that was it. He was gone. Even though our degrees were thirty years apart, he was treating me like an old chum, reminiscing about his times at the college bar, where he insisted with a chortle and a wink that he’d had ‘many a wild night’.

He went a bit misty-eyed talking about those days, which isn’t that surprising really. I only left three years ago and sometimes even I get misty-eyed thinking about it. Probably because everything has gone a bit awry since. I moved to the States for university convinced I’d make it big here, but now I’m beginning to think there’s a reason my dad, who grew up in New York, left to marry an English woman and live in Cornwall. Because while my student days were idyllic, it turns out real life in Manhattan is nothing like the dream world of a liberal arts university. The chaotic streets of New York bear no resemblance to the tree-lined pathways of the campus; people in the city don’t spend hours having picnics and reading poetry; and a degree in photography, although widely revered among my college peers and considered of utmost importance by my professor, seems to hold little to no currency in the real world. I’ve found that out the hard way, which is why I’m here, trying to clinch this job, which despite being a bit shady, is surprisingly well paid. Well, by my standards anyway. It pays twice as much as my last job as a barmaid and I’m pretty sure I won’t have to wash pint glasses or deal with annoying drunks. Although you never know.

Derek studied an equally impractical course – media studies and communication skills – and from a quick Google search this morning, it doesn’t seem like he’s managed to put it to much real-world use either, unless he was a very communicative boss in his former career as an adult entertainment company director. Or in his stint as a used car salesman. Yep, it’s fair to say that neither of us would quite make the list of our college’s star alumni. Despite Derek’s questionable background, his latest venture, To the Moon & Back, seems to be doing surprisingly well. The company won Dating Agency of the Year at the prestigious US Dating Awards a few years ago. And it’s received a ton of rave reviews online with former clients claiming that thanks to the agency, they finally met the love of their life after years of struggling to find a partner. It was even profiled by The New Yorker, which described it as an, ‘innovative and ambitious dating service with a friendly personal approach’.

The website of To the Moon & Back is incredibly slick too, which is why I was a little surprised when I rocked up to find that in person it consists of nothing more than a client lounge and a cramped back office. With a central address on Wall Street, I thought it was going to be as swanky as its zip code, but it’s tiny. Located at the top floor of a financial advisory firm, it’s nothing like the salubrious offices below. The client lounge, which Derek showed me through earlier, is like a kooky cocktail bar, with a huge sofa laden with sparkly cushions and throws, two comfy armchairs, an ornate coffee table, low-hanging gold lamps and sumptuous curtains. Leading on from the lounge is this pokey office, which features Derek’s worn-looking old desk, a dated Mac computer, a filing cabinet, a shrivelled pot plant in the corner and an incongruous and oddly distracting waving Chinese cat ornament which sits proudly next to Derek’s monitor. Derek told me he’s been running the whole operation himself since he launched the business two years ago, but apparently, he now needs extra help looking after his client list of ‘successful single bachelors’ and fighting off competition from rival agency, Elite Love Match, which Derek claims are ‘scum, a bunch of charlatans, the worst dating agency in New York’.

Derek’s stomach growls and he reaches into his desk drawer, pulling out a pack of Oreos.

‘Fancy a biscuit?’ He thrusts the pack towards me.

‘Sure!’ I reach for one, smiling gratefully.

Derek sips his coffee and takes a bite.

‘So…’ he ventures through a mouthful of crumbs. ‘Where would you suggest taking Erica for a first date?’

‘Oh!’ I feel my face light up. Now this is my forte. I may not be a natural when it comes to love, but I do know New York’s fine dining scene inside out.

Not because I frequent such establishments, just because I know them. I read about them. I follow every major food critic in the city on Twitter and I have an encyclopaedic knowledge of Manhattan’s high-end dining scene. I suppose it’s to me what Second World War history is to Andy Graham. These places represent the glittery side of New York. The side of the people who’ve made it. The holy grail, if you will. And yes, I’m more likely to order in from Domino’s than actually go to such places, but I like knowing that they’re there. Just in case.

‘How about Zuma?’ I suggest. Zuma is a new Japanese fusion restaurant in Midtown. It was opened a couple of months ago by a Michelin star chef and it’s been getting rave reviews.

‘Interesting, why Zuma?’ Derek asks.

‘Well, the food’s meant to be great, but it’s also classy and cool. It’s not just your run of the mill bar or café, it’s the kind of place you take someone to impress them and I think Erica would feel complimented by the choice. It sets a good standard for a first date. Oh, and it’s not far from the Upper East Side so it’s convenient for Erica too.’

‘Very convenient! Especially if she and Andy hit it off,’ Derek adds, raising an eyebrow suggestively.

‘Yes,’ I laugh awkwardly.

‘Zuma is a great choice,’ Derek says. ‘Have you been?’

‘No.’ I admit. ‘I’ve just heard about it.’

I’m about to ask Derek if there’ll be any opportunities to go to such places within the job role. The online ad mentioned ‘networking with clients’ and you never know, such networking might take place in fancy bars and restaurants, particularly if the clients are as successful as Derek makes out. But as I open my mouth to speak, a buzzer sounds, a shrill bleep chiming through the office.

‘Sorry Polly, I’d better answer that.’ Derek gets up and crosses the room.

‘Hello?’ he answers, pressing the button on the intercom. ‘Brandon! Sure, come on up!’

I glance over my shoulder to see Derek buzzing his visitor up.

‘Brandon’s one of my clients. Great guy,’ Derek tells me, with a warm smile. ‘He’s a super successful lawyer, a real high-flyer but not so successful in the love department.’

‘Oh…’ I utter regretfully.

‘Yeah, well, I’m working on it.’ Derek sighs.

‘Right.’ He claps his hands together. ‘I’m going to have to wrap things up I’m afraid,’ he says, pulling a face, as if calling time on the interview is going to come as a major blow to me. ‘But it’s been excellent meeting you, Polly.’

‘It’s been excellent meeting you too!’ I enthuse, a little too brightly.

Derek smiles at me with that broad paternal smile and I smile politely back. I put on my jacket and we head out of the office.

‘“I’m going to court you!”’ Derek chuckles as he leads me back through the client lounge. ‘I think you’d be a natural at this job, you know.’

‘Really?’ I ask with slight trepidation as we pause at the exit.

‘Yes, really.’

Derek reaches over to shake my hand. ‘Thanks for coming in. I’ll be in touch very soon,’ he says, with a conspiratorial wink. A wink that tells me, without a shadow of a doubt, that the job is mine. Any sliver of doubt I had has now been wiped out. It’s in the bag and for the first time in my life, I feel both relief and dread at the same time. My dream has always been to be a photographer, not a matchmaker, but money is money.

I pump his hand, thanking him, before heading out the door.

As I walk down the narrow office corridor with its ugly hexagon-printed carpet, I try to imagine pacing down it daily. Every morning and every evening. On my way to and from that tiny office with Derek and his waving Chinese cat. Could this be my domain? My new life? My new routine? Could I look at this ugly hexagon pattern every day? This building and this job are hardly where I imagined I’d end up.

‘Excuse me.’ A male voice interrupts my thoughts and I look up to see a man, an incredibly handsome man, who must be in his early thirties. He’s tall, with dark hair and striking blueish green eyes.

‘Sorry!’ I move out of the way to let him pass. He’s wearing a smart grey suit and carrying a briefcase; he looks every inch the corporate city worker. He must be here to visit the financial advisory firm downstairs. ‘Umm, that’s To the Moon & Back,’ I inform him, gesturing down the hallway. ‘You know, the dating agency.’

‘Yes.’ The man smiles. ‘I know…’ He eyes me with a bemused look. Then suddenly, it dawns on me.

‘Oh! Are you Brandon?’ I ask, fully expecting him to say no. He is definitely not how I imagined Brandon. Or any other of To the Moon & Back’s clients, for that matter. In fact, when I pictured them, I envisioned different incarnations of Derek: balding, overweight and middle aged.

‘Yes… and you are?’

Yes? I try not to gawp. Brandon?! How is this guy Brandon? How is he single?

‘I’m Polly. Polly Wood. I just had a job interview with Derek,’ I tell him, with an awkward laugh.

‘Right. Nice to meet you, Polly,’ he says, with that bemused, sparkly-eyed look.

‘Nice to meet you too!’ I reply.

He smiles, causing the skin around his eyes to crinkle and dimples to appear in his cheeks. He has the most perfect smile. In fact, everything about him is perfect. He’s around six-foot tall but not too towering. He’s slim and lean-looking, and even though he’s wearing a suit, I can tell he’s muscular without having the ripped build of a gym addict. He looks clean-cut with his corporate suit and short brown hair, but he doesn’t look boring. His eyes tell you that there’s more going on and a light dusting of stubble along his jawline makes him look sexy rather than slick.

‘Well, good luck! I hope you get it,’ he says, and for a second, our eyes lock and a charge of intensity passes between us.

He hopes I get the job? So he can see me again? I can’t quite figure out whether he’s just being polite and glib or if he actually wants me to get the job so that our paths might cross. Because I, for one, would definitely like that.

‘Brandon!’ Derek bursts through the door, arms outstretched as though greeting an old friend.

‘Derek!’ Brandon turns towards him with equal enthusiasm.

‘See you around, Polly,’ he says, smiling over his shoulder before heading down the corridor.

‘See you,’ I echo as I walk away.