Flirting up: how to woo Mrs Robinson (tip one, don't call her that!)

Time was when all the talk was of cougars on the prowl to seduce the nation’s youth. Now it’s the nippers leading the way, most notably on the Burberry front row where the 19-year-old reverse-cradle-snatcher-in-chief Harry Styles flirted with Sienna Miller (31), and on BBC Breakfast where Alex Turner (27) indulged in some flirty badinage with Susanna Reid (42). And one can see the appeal. The older woman presents the most consummately packaged challenge.

However, the path to actually seducing the older bird is not a straightforward one. With age comes confidence, discernment and the ability to see through the more callow move.

In my late thirties, I found myself bowled over by the most beguiling youth: interesting, interested, with considerably more winning ways than men twice — oh, alright, three times — his age. On the other hand, I have also had to swiftly detach myself from a twentysomething with a mummy complex, and another who appeared to associate the situation purely with porn scenarios. So pay attention, boys, here’s how it’s done:

1) Raise your game

This woman has been round the block. She has taste, refinement. A night at Nando’s isn’t going to cut it (although, in fairness, this may work for Caroline Flack). This does not imply throwing money at the situation, merely thought. That brilliant little local Sardinian you discovered: perfect. A Tex-Mex chain: think again. And let her pay, not least if she wants to go somewhere fancy. She earns more. Why not? Although do offer to go halves. You’re not a gigolo. Well, not officially.

2) Flatter

Flattery is key — the entire situation should be mutually flattering — but try to keep compliments grounded within vague reality. The best line I have encountered was issued with an air of genuine innocence. Youth: ‘Are you back at college tomorrow?’ Me: ‘I’m a tad older than you, sweetheart.’ Youth: ‘Like 22?’ Cue mass swooning. Do not use the phrase ‘Mrs Robinson’, or refer to how much she has to teach you. Charm is all. Indeed, sans charm, there is no point in you whatsoever.

3) Play to your strengths

Fundamentally, you may not yet be very interesting beyond a certain clinical fascination. What you do have is time, thought, attention to bestow, a beautiful body, enthusiasm, and a compatible sexual appetite. That thing about 19-year-old men and late thirty- and fortysomething women sharing the same erotic energy? Nothing but the most fortuitous truth. You are also not as self-absorbed as males her own age. Conversation-wise, avoid Nineties references to Power Rangers and the like, and expand your horizons beyond gap yahs and the relative merits of the latest hair products (Styles, we’re talking to you).

4) Embrace the role

You are obliged to fit in with her life, not her with yours, not least as hers is the more thrilling and established version. Accept and enjoy your secondary status. You can continue to lord it over girls of your own age who are yet to establish a style, sport self-plucked, Cubist eyebrows and an uncertainty regarding what to do with their breasts. But, here, you’re out of your depth and that is the beauty of the thing. Relish the objectification and your status as a sex object. Look the part. And don’t expect her to come to your gaff: that’s a retro step too far. Similarly, she won’t be hanging out with your friends — even you will have dropped them in another five years.

5) Expand that brain

Do try to keep up. Read a newspaper perhaps? Take some fish oil. I once had to explain who Margaret Thatcher was to a nipper-ish suitor. Another pal, truly, asked who the woman on all the bank notes was. A complete lack of material between the ears will prove something of a deal-breaker. Think of this as gaining your A* in vague social awareness.

6) Grow up

For you this may be a rite of passage, for her it’s intercourse. Don’t pretend it’s forever, but neither should you allude to its limited shelf life. Being obvious about its unfeasibility is as unnecessary as it is rude. Be discreet. No bragging to friends, tweeting, or gratuitous Facebooking. When it ends, try to make it look as if she’s called time, which she probably will. And no pleading, sobbing, or stalking. Both of you should aim to emerge with fond memories, as friends — adult behaviour that also doesn’t rule out an equally adult re-match.