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What Are the Benefits and Challenges of Dating Older Men?

I have a particular interest in health, spirituality, fitness, and the mind-body connection.

Older men can have sophisticated tastes; are you ready for that?

Older men can have sophisticated tastes; are you ready for that?

How Much Older Are We Talking?

We all remember when 27-year-old Ashley Olsen made headlines for reportedly dating 47-year-old Bennett Miller, the director of Moneyball. And yes, I know some younger men date older women. Kyle Jones, a 31-year-old Pittsburgh man, raised eyebrows for having a relationship with 91-year-old great-grandmother, Marjorie McCool. All that to say, I am not being sexist, however, this article is about younger women falling in love with older men (and I don't mean a few years older).

Let's address the fact that there exists this notion the woman who dates the old guy has turned against her kind. This is because she's giving into the cliche that men should be providers while the woman should be the trophy. However, the practice is actually not only been customary, but even advisable. There are biological and psychological reasons for this.

For instance, we all know that girls reach puberty sooner than boys, their bodies are ready to have children earlier, and they only remain fertile for a limited time period. Psychologically, they reach emotional maturity much sooner than men. In fact, statistics prove that, on average, American men usually marry younger women, even though these marriages are destined to fail.

A study by Thomas Pollet and Sophia Pratt revealed that married women were 4.1 years younger than married men in the United States. According to the same study, successful men featured on the Forbes 400 list married women seven years younger. The numbers get even more interesting. When these super-rich men remarried, their subsequent partner was substantially younger, 22 years younger on average. That's the kind of gap I will discuss here.

Does the Psychology Reveal Daddy Issues?

The common question is do women who date older men have daddy issues? The short answer is sometimes. Marianne Vicelich, relationship expert and author of Destruction: Free Yourself From The Narcissist, explains that “[i]t’s been well documented that . . . the subconscious mind may crave a ‘father figure’ who’s able to protect, adore and provide you with the affection you missed in childhood. The problem with this scenario is that it may bring an imbalance of power to the relationship.”

This point is emphasized by Pepper Schwartz, Ph.D., who states that “a woman can have a healthy relationship with her dad and still be looking for that father figure in a spouse . . . [i]t’s not that these women are sexualizing their dads, but the things that a dad represents." In fact, a recent study of self-identifying women, it was revealed that 74% of them claim that the "daddy issues" phenomenon did not apply to them and the age gap in their relationship.

Hollywood's unsuccessful love story: George Clooney with his younger girlfriend Stacy Keilber.

Hollywood's unsuccessful love story: George Clooney with his younger girlfriend Stacy Keilber.

Why Do Women Choose to Date Older Men?

  • Financial Gain. Money seems to be the obvious answer, so I will get it out of the way. If a woman were to marry a man the same age or slightly younger then her then they would be more likely to struggle initially until they both can plant their feet firmly into their respective careers. Such a dilemma could result in the search for financial security in a relationship with an older man.
  • Life Experience. Experience is an attractive quality. Older men tend to be more evolved in all areas. They have a certain confidence and internal stability about them as a direct result of their age. Women aren't always looking for monetary wealth—wisdom and emotional intelligence are just as appealing.
  • Better Sex. We often think that younger men can provide the bedroom tussle of our wildest fantasies, but that is not always the case. Sometimes, an older man's experience can lead directly to transcendental sex because he has had time to realize what may have been effective and ineffective in the bedroom.
  • He's Just Like Pops. As mentioned earlier, a woman may marry a guy that reminds her of her father. It is normal to seek out the protection and care that you're accustomed to. Such a caring and loving attitude is usually found in older men.
  • Fewer Games Played. Older men are more trustworthy a lot of times as a result of their life experiences. This means that they are often less promiscuous and more committed to being a person that makes you feel secured about settling down.
  • Emotional Reliability. Finally, it is easier for younger women to relate to older men. Women in their 20s are usually still trying to come to terms with their identity while dealing with the ups and downs of emotional development. They need a strong anchor to keep them centered, and a mature man can provide that emotional stability.

The Cultural History and the Modern Trend

Historically, age gap pairings were common and, often times, the rule. Thirty-year-old men would typically marry girls in their mid-teens in Classical Greece. It is well-known that men of power and prestige would also take young women as lovers and wives. Monarchs like Henry VIII chose women far younger than himself. Many arranged marriages also involved husbands who were much older than their wives.

In modern times, online dating sites have made it easier for women to find men of all varieties. In fact, many are full of married men pretending to be single or divorced. Because such websites attract more men than women, they often offer women incentives such as free registration and discretion. All of this makes it easier for younger women to meet and date older men.

Cary Grant paired with the much younger Audrey Hepburn in the film "Charade."

Cary Grant paired with the much younger Audrey Hepburn in the film "Charade."

Why It's a Bad Idea to Date Older Men

Let's get into some of the problems that you may encounter when dating a guy who is much older. To get an idea of the possible challenges, you only have to read the experiences of women who have married old men. These tragic stories are all over the internet, so I will be very blunt in the list below.

  • Physical compatibility could be an issue. You will be in the prime of your life, and he'll be rapidly approaching the end of his. While you are spending hours in the hospital because he has fallen ill, your friends will be sharing stories about their baby showers and their children's sports activities.
  • If he is married, then you will be his second choice. His wife and his children will always be his top priority, which is why he is still married and you are his mistress. This leads me to my next point . . .
  • If you wish to start a family, then there might be emotional and physical barriers. An older man's sperm usually cannot produce healthy babies. Physically, he may not be able to do all the activities with your child that are expected of a father. Emotionally, he may not be ready to create competition for his kids from his previous marriage.
  • Navigating between the various social circles, including family and friends, can be challenging and culturally shocking if you are not familiar with the crowd. The difference in conversation and social expectations are areas that will highlight the age difference in an unfavorable light.
  • Once a cheater . . . If he can cheat on his wife with you, he can cheat on you.

How to Make the Relationship Work

The benefits of dating an older man are very few, and most fathers would have a hard time if their daughters began to date one. To be fair, some couples have successfully lived together despite the age difference.

Here are some tips to make your relationship work:

  1. Communicate. This is the number one game-changer in all relationships. Despite all your differences, it is the willingness to talk that keeps the flame burning bright. Talk to him, listen to him, and share ideas. Discuss things you like and dislike. Talk about your future plans. That's one good thing about marrying an older man—he listens better than a younger one. Read a lot so that you can discuss politics, entertainment, and sports. That brings me to my next point . . .
  2. Share common interests. Try watching sports or his favorite type of films with him, and find aim to find them genuinely interesting. Also, get him to do the same for what you love to do. Doing things together improves communication, which I highlighted in my previous point.
  3. Give each other space. Yes, I just said that you should find things to do together, and I am not trying to be contradicting. You should spend time apart so that each of you can do the things the other doesn't like on your own. There's no point trying to force your man to go shopping with you, for example. Let him catch up with a buddy over a beer while you go and spend his money. You will need to find the right balance between doing things together and being independent.

This content reflects the personal opinions of the author. It is accurate and true to the best of the author’s knowledge and should not be substituted for impartial fact or advice in legal, political, or personal matters.

Questions & Answers

Question: I have recently started dating an older man. We have been friends for over two years now. We started dating about a month ago. He is sixty-three, and I am thirty-nine. Our issue seems to be that he thinks people are judging and looking at us. We have a lot of mutual friends. Nobody is judging or looking at us. How can I get him to realize that nobody has an issue with our relationship? How do I make him more comfortable in public with me?

Answer: If he is in love with you, he will be able to ignore any judgmental behavior from friends and family - if such behavior exists. Else, he is probably using it to disguise his lack of commitment.

Question: I'm nineteen and he's thirty-four. We have everything in common. We met at work. He's been divorced for five years, and has been on his own ever since. He's shy. Are we two peas in a pod?

Answer: If you find that the two of you have a lot in common, then you can nurture this into a fruitful future for both of you.