Shipping to
United States
Illustration by Mr Antony Hare | Words by Mr Simon Mills

The best dating movie in recent history was 2011's Crazy Stupid Love, mainly because it stars the unassailably sexy, thinking man's dream triumvirate of Mses Julianne Moore, Emma Stone and Marisa Tomei. But also because Mr Ryan Gosling's Jacob Palmer, a sharply dressed, smooth-talking, bar-flying serial shagger, offers a series of refreshingly accurate lessons in modern-day dating to Mr Steve Carell's clueless, tongue-tied, recently separated, slope-shouldered, emotionally broken fortysomething, Cal Weaver. The segment about the two male leads' wildly disparate approach to wardrobes is particularly well observed.

While Mr Gosling's cruising attire is styled for results - even at the mall, even while eating a slice of pizza - Mr Carell's character has seriously let himself go, all the way into Silicon Valley territory. "Are you Steve Jobs?" asks Mr Gosling, incredulously. "Are you the billionaire owner of Apple computers? No? Then you have no right to wear New Balance sneakers. Ever." A high-tempo shopping montage ensues, in which Mr Gosling forces his hapless middle-aged project to invest in a capsule wardrobe of contemporary dating schmatta. Mr Carell winces at the designer prices. "Be better than the GAP", says Mr Gosling. "Say it."

A single man's clothes, dating clothes, are not just for dressing; they are carefully executed gift wrapping, a visual CV that trumps up sartorial proficiency and alludes to bank balance, taste, a wider aesthetic, career choice, worldliness and confidence. Make no mistake, every detail will be noticed, dissected and forensically appraised by your date just moments after your entrance. This is dating CSI, baby - and you, my single friend, are the "vic". So, during that first encounter you want her to see your best bits and disregard your imperfections. You want clothing that slims, enhances, elongates and sexifies, not just insulates.

Being yourself on a date is a good thing, but you might do well to not reveal as much as Mr Bradley Cooper and Ms Jennifer Lawrence do in this café scene from Silver Linings Playbook

Make tailoring your friend. Ditch anything loose, oversized, baggy, sloppy, avuncular and/or daddish. Wear items that encourage confident, upright deportment. Keep tones dark and sober. Maintain a palette of muted, classy colours: navy, petrol blue, black, white, grey, and so on. If you go for jeans, opt for indigo blue, with a selvedge, and fitted as if for an urban rodeo. Footwear? Proper bench-made shoes, please. Never opt for sneakers on a date. She'll think you are one of those unemployed sorts with a PlayStation problem.

Best to lie up when asked your age but to dress seven to 10 years younger. If you are, say, 45, think 37 with your cut of trouser. If you are wearing a suit, lay off the pinstripes. This is a date, remember, not a sales pitch. (And, while we're at it, your mobile phone number handwritten on a napkin - replete with playful message - is much sexier than proffering a business card detailing your direct line at the office.)

Just before you leave the house, look at yourself in a full-length mirror and cast a cruelly critical eye over your ensemble and ask yourself: if you walked into a bar and bumped into you, would you like to take you home? If the answer is anything as positive as "maybe", then you are ready to hail a cab.

A single man's clothes are not just for dressing - they are a visual CV that alludes to bank balance, taste, career choice, worldliness and confidence

Now comes the tricky bit: talking. It's worth noting that Mr Gosling's best chat-up line in Crazy Stupid Love was, after a female had said she didn't know what she was doing tonight, "That's OK, I do." And as lines go, it is a pretty slick one. Crucially, because it came out of Mr Gosling's mouth. And not yours. The truth is that actors, fictional characters and rock stars tend to have an unfair advantage over us civilians. Their celebrity is, in effect, an opening gambit in itself, so there is no need to lay on the cheese. Don't believe me? Here are the apparently fail-safe opening lines reportedly employed by two well-known swordsmen.

Mr Rod Stewart: "Hello darlin', what have you got in that handbag?" (He apparently used this to chat up Ms Rachel Hunter.) Sir Mick Jagger: "Hello, I'm Mick." The latter one being the most effective, especially if you happen to be Sir Mick, of course.

But if you don't happen to be an A-list superstar, being funny, cheeky and gently audacious is always a winner. Even if it's civilian you, trying to nail a celeb. I lunched with the pillowy-lipped supermodel Ms Rosie Huntington-Whiteley recently and she told me that (pre-Mr Jason Statham) she'd been very nearly seduced by a guy in a bar who had a moustache tactically tattooed on his forefinger. When he caught Ms Huntington-Whiteley looking at him across the room, the handsome boy raised his inked digit to his upper lip and waggled it. With that goofy move, the stranger came this close to pulling a Victoria's Secret Angel. If only he'd known.

That said, any seasoned singleton will tell you that venue is more important than ink or vernacular. Regard everywhere you go (with the possible exception of work) with priapic potential. Hunting grounds such as nightclubs and cocktail bars are OK when you are in your twenties, but cougars and DILFs prowl parks, supermarkets, cinema multiplexes, service stations, weddings and middle-class family dinners. Contact may be made by swings and sandpits. At checkout queues and butcher counters. ("Hello darlin', what have you got in that trolley?") After initial contact, send a pithy, funny, grammatically correct and spell-checked text message minutes after your initial encounter (when you have vacated the venue) suggesting a second meeting.


Once you go out for dinner (for which you will be picking up the bill and paying for the taxi afterwards) she'll be liking intellect and goofiness in equal measures. Be urbane, informed and a very, very good listener. You should be subtly, sexually driven but not salivating for it. So don't ogle, because you'll look desperate.

Be miserly with the compliments (let's face it, if she's pretty, she'll have heard them all before), but make the ones you do deliver thoughtful, memorable and truly devastating. If it's a first date, whatever you do, don't touch her. Instead, pay rapt attention to everything she says, no matter how annoying and silly it might be. Nod in approval and be sympathetic and understanding. You should know that it is quite possible to endure a whole evening with a first date without her asking a single thing about your own career and personal life. You have to learn to not be surprised or offended by this.

However, when you get the chance, make it very clear that sex - maybe even a relationship and babies - is what you eventually want from her. You don't want to go on three expensive dates, having invested in some nice clothes and put aside your beloved New Balance sneakers to suddenly have her announce that you have become her "friend", now do you?