Should I sleep with a toyboy?

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Actors Anne Bancroft and Dustin Hoffman appear in a scene from the 1967 film The Graduate.

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QUESTION: My marriage ended two years ago and the closest thing I’ve had to a relationship since then is a flirtation with a younger man (19 years my junior). He calls me Mrs Robinson, tells me that I’m sophisticated and hot and begs me to “educate” him. I’ve started to feel attracted to him, too, but I’m scared to pursue the matter because, despite his insinuations, I feel gauche about sex. I have slept with no one other than my ex for 20 years. What should I do?

ANSWER: The Graduate has a lot to answer for, doesn’t it? Mrs Robinson’s seduction of naive Benjamin left a million men fantasising about an older woman in fancy undies who would show them the ropes.

All the talk of cougars has only propagated the notion that what every woman of a certain age wants is to issue her own diploma in love lessons. That’s all very well for Madonna and her uber-confident ilk, but what about the rest of womankind?

The truth is a great many women (and men) feel confident about their sexual prowess only with their long-term partners. After all, you’ve spent years learning about that individual’s body, but that doesn’t make you an expert with anyone else’s. So, if your relationship ends after many years, you’re bound to feel nervous about your next lover.

The worry among readers who contact me after long relationships have broken down is that the dating world will have moved on and they will no longer understand the rules of sexual engagement.

So much for the poise, knowledge and sophistication that is supposed to come with old age!

I think most of us feel jittery each time we embark upon a courtship. Sex with someone new represents a daunting act of intimacy, because no one sees you in such an intimate state as your lover.

Added to this, there’s the fear the chemistry that has brought the two of you to the bedroom may drop away like the clothes on the floor.

So what to do about your young suitor? You don’t need to have read Susan Jeffers’s Feel The Fear And Do It Anyway to realise on certain occasions that’s sound advice.

You’ve been on your own for two years, your confidence is low and you are finding it hard to think about yourself as a sexual being. Yet here’s this admiring young man who has spent months pursuing you.

I am sure this man is drawn to you because you feel at ease in your own skin in a way that’s uncommon among the young.

You’re worrying unnecessarily. You think you should display a range of courtesan skills, when all this man probably wants is a woman who unabashedly likes sex, doesn’t mind the lights being on and might - just might, if he’s very lucky - wear stockings.

You need to ask yourself what’s the worst thing that can happen in this scenario. The answer is you end up feeling the earth didn’t move. Well, that can happen with any dating scenario, no matter the age of your suitor.

And surely the upside about being mature is that you can take a bit of disappointment. - Daily Mail

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