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Dating A Woman 20 Years Younger

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Avoiding the traps and managing the expectations

Older men (40+) have an advantage in the dating pool. They are sought after by women of their own age and can compete quite effectively for women much younger than them. In fact, if you are over 40 you may have noticed that you get more attention, more batting of eyes and genuflecting of face, from girls in their 20s than you ever have.

There is some truth to the popular notion of younger women going for older men. Since passing the threshold which marked the beginning of my fourth decade on this planet the experience of being constantly checked out and flirted with by college girls and young professionals has been most pleasant and surprising.

Such older-younger matches are perfectly natural. The tight bodies, perky tits, perfectly cleft assess, and promising freshness and even naivety of younger women make the prospect of taking one as a lover very appealing. But there is something deeper than these surface charms.

You know more now than you did when you were her age, and you were chasing girls like her. You are more experienced, more confident about who and what you are, you have seen more of the world, have met different kinds of people, and managed your way through more problems and difficulty than your prospective young mistress. You feel that you will be in a position to more easily master her emotionally, mentally, and sexually, which is mainly what draws you to her.

There is little doubt that she feels something that is the reverse of this. Most young women who go for older men are attracted by their maturity in all areas of life. Your young nymph will like the fact that you are settled in your profession, financially stable, and emotionally controlled. She will be attracted to your steadiness and dignity. If you have kept in shape, your physical attributes will delight her—as men get older they become more defined in their faces and bodies.

However, it is not all fun and games. There are challenges to dating a woman who is so much younger than you—actually, more like traps to avoid and expectations to manage. Here are a few of them.

The father figure conundrum

It is easy for her respect and deference to slip into daughterly feelings. Freud said that a girl’s first sexual feelings are toward her father. Only when she grows up and learns of its taboo does she cast her eye elsewhere. But those early instincts do not completely vanish, which is why many women are attracted to men who are like their fathers.

In herein lies your conundrum. On the one hand, you do not want to her to associate you too much with her father, which may lead her to draw away from you; on the other hand, you should not mind it too much if she does because it may be what she most likes about you.

She may seek your advice on important decision. Your age, experience, and bearing may make her think of you as someone she can confide in. And the fact that you can see exactly the trouble she’s heading toward or has experienced may compel you to give her some sage wisdom and a bit of comfort.

But be careful. Don’t be too fatherly or that is what you will become to her. The best course of action is to balance the serious talk with reminders that you still view her as a sexual being. Offering her advice and a shoulder to cry on should be offset by constant flirting, touching, and complimenting.

Her wastrel friends

Another difficulty you’ll encounter is her no good friends. She may be a high achiever and a person of substance, but it is inevitable that one or two of her friends will be complete losers. She can’t see it, but you can. You will clash with them. They will perceive you as a threat, as someone who might expose their lack of talent and ambition to your girl, who is likely to be one of the few people to tolerate them.

The best response is to avoid being around them. Although she may want you to hang out with her when she is with her friends, it is okay to take a pass. You will probably find it hard to find common ground even with those of her friends who aren’t wastrels. Don’t subject yourself to torturous nights with people you will never get along with.

Your career needs

Finally, you must look after your career needs. Plenty of older men have much younger women on their arms when they go to corporate functions. However, if you have reached a senior level in your profession you cannot risk going out with her a girl who does not know how to handle herself in such an environment. Any girl who you want to date regularly must be equipped to function as your companion when you meet and socialize with the peers and colleagues of your profession.

About Christopher Reid

Chris was born in Washington, D.C. and lives in Britain. He works as a blogger, essayist, and novelist. His first book, Tea with Maureen, has just been published.

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