Dating Older Men — 6 Reasons You Might Want to “Date Up”

Women's Dating

Dating Older Men — 6 Reasons You Might Want to “Date Up”

Michelle Johnson
Michelle Johnson Updated:

A few years ago, I spent several hours people-watching in an outdoor café on the coast of the Italian Riviera. As the yachts pulled into the harbor, I saw a few well-heeled young women with fit bodies disembark on the arms of tanned, distinguished older men. This type of relationship can sometimes be seen as a quintessential stereotype in dating: a perceived man of power, wealth, or prestige with a gorgeous younger woman on his arm.

However, most women who have dated men years or even decades older, myself included, are often motivated by other, less conspicuous, and more genuine reasons. Let’s explore some potential advantages of taking a second look at the next older man who comes your way.

1. He’s His Own Man

As a result of his age and life experiences, a mature man frequently has deeper clarity about what he wants in love and life. He’s more secure in who he is and has a resumé of established accomplishments. His confidence level is high, and he’s proven his value in the real world.

Photo of Hugh Jackman accepting an award

Older men are often more secure in who they are and have a resumé of established accomplishments.

A man like this can be more direct and more authentic in expressing his feelings, and a man like this is often not at all interested in playing silly dating games. More than likely, he’s graduated from the playboy stage and is ready to share his life with the right woman.

2. He’ll Help Broaden Your Point of View

An older man has the advantage of more life experience and the benefit of hindsight. You can probably learn a lot from him, and he’ll enjoy being appreciated for his hard-earned wisdom. There’s something appealing about the combination of retro and modern — and this also applies to relationships. He might introduce you to his timeless favorites in music, movies, and cuisine, and you’ll add some spice, variety, and vitality to his established repertoire.

3. You Can Grow Your Family & Make New Friends

While your primary relationship is going to be with your man, it’s not uncommon to “inherit” some relatives and new friends when you date or marry someone older. It can be fun to become a part of his inner circle and for him to become a part of yours.

Photo of Brad Pitt and Angelina Jolie's family

If one or both of you have kids and a lot of friends, it’s fun becoming part of each other’s inner circles.

While some women may not see this “inheritance” as a perk, others do find it very satisfying. One successful career woman I know who married a divorced older man now also relishes her new role as a second mother to her husband’s children. She says this has added so much richness to her life. There could be some initial suspicion or resistance from his friends or family if you are seen as an interloper, but most people are likely to be very welcoming.

4. He Knows How to Please a Woman

The debate rages on about whether youth tops experience in or out of the bedroom. Still, you have to admit there is something pretty intoxicating about being with a man who has the finesse to woo a woman. He can plan a real date and take the romantic lead. A man who has mastered the nuances of dating and romance won’t have to do as much on-the-job training because he’ll already know how to make you happy.

5. He Probably Acts More Youthful Than His Chronological Age

I’m not sure 50 is the new 40 or 60 is the new 50, but many men are becoming increasingly health-conscious as they age. These men keep their bodies in good shape and stay physically and socially active. The result is a more youthful appearance combined with the sophistication that comes along with a few gray hairs. This kind of man can energetically match a younger woman and maintain a robust sex life. He may even give you the credit for keeping him young!

Photo of George Clooney playing basketball

Don’t let the number fool you — most older men have more vitality than you’d expect.

6. You Can Combine Resources to Build a Stable Life Together

Clearly, many older men are more established in their careers and are more financially stable. I’m not recommending that you take the gold-digger approach to finding love. However, once you are in a dating relationship, you may decide to share or combine resources.

Even if neither of you is particularly well-off, these dual assets could supply additional financial security or the chance to consider a new lifestyle or career options. You may decide to travel the world, start a new business, or pursue other big dreams on your bucket list.

Age is Just a Number, Right? Give Older Men a Chance!

Take it from a woman who’s dated an older man — don’t let the stereotypes cloud your judgment. We truly never know who we’re going to fall in love with. You’re probably a strong, smart, successful woman in your own right, and you may not feel like you need a man to make your life complete, let alone an older man. Yet, even the most self-sufficient women enjoy a soft place to land at the end of a long hard day. You just might find that safety and security in the arms of an older man.

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