The other night I had a long call with a close friend who is working abroad – one of those long-distance Skype check-ins where both have so much to say yet both struggle to have a fluent conversation. I don't know, maybe it's the 'laptop' effect – the feeling that you're either conference calling or being interviewed instead of having a chat. Anyway, one point of anxiety was his imminent date with a friend of a work colleague's partner. This prompted a length digression into single life and the games we play. 

It's been quite a while since Dave has been in this situation. He's not the dating kind: a self-confessed introvert if the Myers Briggs sense – his words, not mine – but certainly a confident guy with a mischievous side. But he's also not the kind of guy to walk up to a girl in a pub or on the street. Some women, and to a much lesser extent men, think around the problem and adopt a systematic approach to the dating game – joining sites, writing profiles, shortlisting, attending, and then ploughing through until the plusses outnumber the minuses and you find someone … acceptable. Attractive, occasionally; attentive, certainly. Tick, tick, tick…

He's very conscientious and reluctantly left London to further his career but he has not formed a large circle of friends beyond a few colleagues and fellow ex-pats, many of whom are in happy relationships. Therefore it has been difficult for him to get 'out there' without the support and encouragement of other single friends. He was shown a picture, seemed curious and was willing to give it a shot. So he sent a text – "a big step for something like me,' he admitted. What saddened me was how expectation, either of himself of what a woman would look for in a man and respond to on a date, was killing the adventure of the night before it had even begun.

Don't get me wrong. I empathise and have felt that tension that many of us feel when a first meeting between two singles becomes an official date. The signals we give and try not to give. The cliched meeting spots – pub, bar, restaurant. The etiquette. After you've got past looks, a hope the other person spends more time gazing at you rather than their phone, there's the challenge of coming across as [add or delete as appropriate] confident, funny, charming, driven … 'normal' not weird. Well, hopefully the latter is not that difficult. Although, if you live in Woody Allen's world where "emotionally disturbed women are sort of interesting" that could be a turn on.

As Jerry Seinfeld said, "Dating is pressure and tension. What is a date, really, but a job interview that lasts all night?" Apparently the secret is to put the other at ease. To relax. To be yourself. Ha! One of life's great ironies: the minute we are told to relax, we become the polar opposite. I did suggest he throw out a few cheesy lines – as if mocking the situation he and this woman find themselves in. A vehement "no", as I expected. "That is clearly absurd advice," he sniped, as if giving one of his most definitive analyses. In truth, and this is a closely linked approach, I favour humour, the self-deprecating variety. Poke fun at yourself and what's brought you here. And why play to the cliche when you can do something random – burlesque cabaret, haunted history walk, life drawing, cocktail making, boat trip or dinner in the dark (that takes looks out of the equation, for one night at least). 

Like any good comedian – and let's face it, deep down we are all hilarious  – it often pays to take a risk, eg making fun of your date's appearance or dipping into the unholy trinity of politics, religion, relationships past. But going through their text messages while they are in the loo, farting or asking them if your rag smells of chloroform may be pushing things a little too far. 

My earliest and most indelible impressions of first encounters have come from films, TV and literature. Real-life experience? Use it but don't be limited by it. So here are a few scenes that remind us all to smile and enjoy the moment.

1. MIA AND VINCENT @ JACKRABBIT SLIM'S – PULP FICTION (1994)

Pulp Fiction was a revelation when it was released in 1994, setting countless teenagers and film-goers on a life-long journey to the outer limits of cinema. Effortlessly hip, entertaining and full of memorable scenes, sparkling dialogue and real characters, Tarantino's best film also featured that wild soundtrack, proving just how crucial the music could be in heightening the mood and popularity of a film. This scene always stuck in my memory because it shows how two strangers can sit at a table and find common ground – even if that is an "uncomfortable silence". Uma Thurman's character Mia Wallace later becomes even more curious about John Travolta's Vincent Vega and the question he is about to ask, uttering "Well, this doesn't sound like the usual mindless, boring getting-to-know-you chit chat. This sounds like you actually have something to say." 

Lesson: speak your mind

2. AKEEM LOOKS FOR HIS QUEEN IN THE CLUB – COMING TO AMERICA (1988)

Some people believe that you won't find smart, successful and stable people, the kind that most thirty-somethings would like to meet on a date, in a club. That's rubbish – it depends on the kind of club. But what this clip from Eddie Murphy's 1998 comedy Coming to America does show is that some things just don't go according to plan. You may find yourself sitting opposite a strange person and whether your best friend is there to bail you out or not, you need to keep calm, smile and work out an exit strategy.

Lesson: it's a numbers game


3. JOEY AND RACHEL'S FIRST DATE – FRIENDS (2001)

This is almost like an outer body experience for Joey (Matt Leblanc) and Rachel (Jennifer Aniston), seeing how each acts differently on a date. The awkwardness of the situation, heightened by the embarrassment that two friends, within the closest bunch of Friends the world has ever seen, are attracted to each other, makes for some really amusing exchanges. It's rarely advisable to cross that line unless you are both care-free enough to put it all down to 'experience'.

Lesson: talk to strangers

4. ABBEY AND DAVE'S IN-FLIGHT LIAISON – THE IMPERFECTIONISTS BY TOM RACHMAN (2010)

One of my favourite books of the past few years is one-time foreign correspondent Tom Rachman's The Imperfectionists. Set in a waning English language newspaper in Rome amid the destabilising digital revolution, Rachman explores events and human foibles through the lives of several flawed characters. We quickly realise that the fortunes of employer and employee are intertwined.

The book is divided into 11 interconnected vignettes and my favourite involves Abbey Pinnola, the newspaper’s chief financial officer, known to her colleagues on the editorial side of the paper by the degrading nickname "Accounts Payable". She finds herself on a plane from Rome to Atlanta, (unknowingly) sitting next to Dave Belling.

Belling is the the copy editor she has just arranged to have fired, one of several casualties as Pinnola tries to keep the paper afloat. In just 20 pages, her perception of Belling is turned on its head: he goes from being annoying, to being bland, charming and attractive. To the New Yorker, Pinnola is (perhaps unfairly) portrayed as being "neurotic, a little desperate, insecure, obtuse." Fair or not, that is her character, it's not Rachman's perception of all women in failed relationships. Pinnola's manic internal dialogue takes hold and she almost manages to talk herself out of a chance for happiness:

“For the next few days, she’s got a four-star hotel room in Atlanta. She gets a tingle. Forget it, you freak. But it would be nice to hang out a bit. Talk. He’s cute, no? Surprisingly. Totally natural. Nice to have a bit of company. A proper grown-up. Having a man around again…”

Regardless of the reasons for Belling's actions, or whether he and Pinnola end up together – I won't spoil it for you – this chapter is a great example of how we agonise and analyse far too much. If there is an ease and mutual interest between two people then that is a great start, surely.

Lesson: don't think, do

5. DAVID BRENT GOES ON A BLIND DATE – THE OFFICE CHRISTMAS SPECIAL (2003)
 

The Office kept me sane while I was working in telesales and trying to decide which career to pursue after finishing university. More than a decade after Ricky Gervais struck gold with his spoof documentary exposing the inane lives of a bunch of misfits at a paper merchants in Slough, the series still holds up as some of the smartest and most agonisingly hilarious comedy to come from these shores.

The two clips above are taken from the Christmas specials, in which the hapless David Brent, ousted from the hot seat at Wernham Hogg and forced to endure further humiliation as a travelling salesman and D-list celebrity, tries to find a date in time for the office Christmas party. In classic Brent fashion he oversteps the mark, dropping wildly inappropriate bombs and pressing self-destruct. To our great amusement.

The moment in the second clip, and Brent's reaction in particular, is something we would all fear in that situation – that's what makes it so wickedly entertaining.

Lesson: lower your expectations; know when to move on


I'm sure there are countless other scenarios from film, TV, literature and beyond that I have missed out. Please add below together with your own personal experiences. Fingers crossed, it works out for Dave.