That was until Jeff had an affair with the school's secretary a couple of years later. Now that was really impressive. She wasn't just older, she was a woman.
Jeff became our hero. While we struggled and begged for even the most innocent affection from girls, Jeff was having a mature and physical relationship with a woman. He captivated us with tales of romantic dinners, weekends in the country, and sex. It made him more of a man in our eyes, yet we never forgot that he was only 17. He was one of us, just a teenager, living the wettest of our dreams.
That is, in essence, the allure of older women. Being with them makes us feel like mature men of the world because they take us seriously when the rest of the world doesn't.
It is probably a good idea to point out the thrill of dating older women only applies to men between 15 and 30 who date women five to 20 years older. If you're 50 and the girl of your dreams is 59, sorry, but that doesn't count. Once you reach the twilight years, age becomes irrelevant.
So why do we want to go out with an older woman? Partly to look like men, without having any of the responsibility. This is something we want as soon as we hit puberty. We begin looking for the quickest way to grow up without doing anything foolish, like getting jobs or acting our age. We shave much sooner than we need to, and spend our savings buying cars. And we dream of dating older women.
Initially, the appeal is purely sexual, as is everything with adolescent boys. Our society is filled with sexual myths. The myth surrounding older women is that they're experienced, uninhibited, and, well, good at it. Really good. Most myths are false, but this one is true.
The attraction is fuelled by the theory of sexual prime. It is said that women hit their peak in their early thirties. Men peak at 19, although most women would argue we reach it at 13 and stay there until we get married. It would appear that Mother Nature herself was dictating such coupling. Guys, get wise. The fact is that older women are sexier.
Malcolm Charles, a 28-year-old computer network salesman, says he has preferred older women ever since he was 21 and in the Navy. He started a romance with Anna Ruth, a 35-year-old lounge singer. For him it was another rite of passage into manhood, similar to those the Navy was putting him through. Now he dates older women almost exclusively.
'The problem with women my age is they're only interested in what you do and how much you make,' he says. 'The last girl my age I dated asked me what kind of car I drove. That was her second question, right after 'How are you?' '
I am dating an older woman, and I can say it's more than just sex. Older women, generally speaking, are more fascinating. They have their own lives, history, careers, ideas. And as Malcolm says: 'They're more interested in your personality and your character than your income.'
He's got that right. This is because they've achieved independence, financially and otherwise. Women over 30, or even 40, have learned to maintain relationships while pursuing meaningful careers. Most are no longer looking for a man who will provide for them.
Malcolm recently dated Diane, a 40-year-old computer consultant. He says it was the most secure, yet free, relationship he's ever had. That's because Diane had chosen long before (when he was still in short pants, no doubt) not to marry or have children. Therefore he never felt trapped. There was an emotional commitment, but it didn't necessarily mean the long walk down the aisle. It made their relationship more relaxed and enjoyable.
'We never had the talk,' says Malcolm. 'You know, the 'Where are we going? When are we going to get married?' talk. We just had a good time. There was no pressure.'
If I'm to be completely honest, that's a major part of the attraction of older women. Often it means no tying the knot, no changing dirty nappies, at least in the foreseeable future. So it's a good way for us to have our cake and to eat it too. All the sex and companionship we want, without ever having to get down on one knee. More often than not, such requests would be rebuffed anyway. A lot of older women who are single are that way by choice. They don't want to get married either.
But here's the catch-22. At least the younger man has the choice. Although we can merrily sow our wild oats, most of us look forward to the day when we throw a ball to our sons, or read bedtime stories to our daughters. We're secure in the knowledge that can do it any time.
Basic human biology means, however, that women must have their children by a definite period of time. If your woman is much older, it can become a problem. It was for Steve Owttrim. Now 29, he fell in love with Katy when he was 22. She was 36 at the time. He dreamed of marrying her and raising little Owttrims, just not right away. But if he was going to, then he had to do it much sooner than he was prepared to.
'I wanted to marry her, but not for a couple of years,' says Steve. 'I had just graduated and wanted to work for a couple of years and get on my feet financially before I got married and started a family. I wanted to wait until I was around 30. But if I waited that long it would have been too late for Katy.' Her biological clock became a time bomb and it eventually blew up their relationship.
It's unfair to say women in their mid- to late-thirties never want children. Some do, and by that age, they want to start immediately. As younger men, we can't ignore it. We have to ask ourselves: 'Do I marry her now before it's too late even though I'm not ready, or do I dump her and find someone my age even though I love her?' Not an easy choice.
But social gatherings are the worst problem. While our friends look at us like men, her friends still see a child. When Malcolm was out with Anna Ruth and her friends, he felt uncomfortable. He was just out of puberty while they were all approaching menopause. The gap between their likes and dislikes was massive.
'All her friends were so much older than me,' he says. 'They all had grey hair, and all they talked about was their careers, homes they owned - the things my parents talk about. I had nothing to say to them. And when I did, they just looked at me like I was a child. If I disagreed with them, they didn't take me seriously.'
And still there is The Look. The 'he-must-be-a-virile-stud' look as we walk into a room with an older woman on our arm. Sure, it's a good way to brag about our sexual prowess without saying a word.
But believe it or not, that can become tiresome. We don't like to be dismissed as toy-boys. One of the reasons we like older women is because they take us seriously. Jokes like 'Do you have to cut his meat for him?' or 'Isn't it past his curfew?' really spoil our delusions of manhood.
The double standard in our society dictates that it is all right for old men to marry girls young enough to be their granddaughters, but women who date younger men must be brazen hussies, hot to trot, or have some personality defect because they can't find men their own age.
Nothing could be further from the truth. The older women I've dated, or I've known through friends have been smarter than most people. They know who they are, what they want, and how to get it. Older women are the most self-confident people I know. And in the end, that is probably what is most attractive about them.