7 Benefits to Dating an Older Man

One of my best friends, Cara, only dates older men. And by older men, I mean men in their early 50s. At first, I was bit confounded. Who would a 30-year old woman want to date an older man with gray hair and wrinkles?! Cara explained to me that men her age are intimidated by her, and just live a different lifestyles. Cara is a successful business owner who manages her own work schedule, takes vacation whenever she wants, can afford luxurious vacations, and enjoys tasteful restaurants. Younger men just can’t give Cara what she wants. Her lifestyle, interests, and goals align with that of older men. Simple as that.

Before I met Cara, my dating pool was limited to men plus or minus 5-7 years of my age. But recently, Cara inspired me to expand my age range and go on dates with men in their early, mid, and late-40s. I’ll admit: Cara is on to something.

If you are a successful, driven woman in your early to mid-30s, I’d highly recommend you expand your age range when dating men. If anything, you’ll learn something about what you want and don’t want in a long term relationship, and you’ll experience a whole new world of relationships and dating.

Below are 7 reasons I’ve started to give older men a chance when dating, and the unexpected benefits of dating an older man.

1. An Older Man Is Not Intimidated By Your Success

I remember the good old days of living in Tampa, Florida. True story: it was a common occurrence for men to be intimidated by men. I’d be flirting with a guy at MacDinton’s with my blonde hair, short skirt, and skimpy tank top, and we’d be hitting it off. Then, he would ask me where I went to school. I’d say, “I went to Emory in Atlanta.” Instantly, he’d look crestfallen and say, “Oh wow. You are really smart.” Shortly after that, he’d abruptly end the conversation and move on. Ouch! I didn’t care where he went to college!

Even when I downplay my education and career, I’ve found that men my age are intimidated. I’ve tried so, so hard to follow the advice in dating books for women. I’ve praised men for their career accomplishments. I’ve sucked up to them. I've played the damsel in distress to show that I need a man in my life to take care of me. (It’s true! I can’t fix a broke dishwasher for the life of me, and I’m helpless with home and car repairs.) It just didn’t work.

An older man won’t be intimated by your career success. In fact, he’ll probably love it. If a man is 10 or 15 years older than you, chances are high that he makes more money than you and has a bigger work title. Older men also offer amazing career advice, as they’ve navigated corporate politics, climbed out of middle management, and have made it to the top.

So ladies, if you are a smart, intelligent woman with a good career going for you, I beg you to please try dating an older man. He’ll support you in your career goals, and you won’t ever have to concern yourself with playing dumb.

2. A Man In His 40s and 50s Knows How to Date

What’s up with younger guys now-a-days? I feel like their mothers never taught them how to be gentlemen. Maybe it’s the millennial culture, maybe younger men were spoiled by their mothers, or maybe men in their 20s and 30s are concerned by the “Me Too” era. Whatever it is, I feel like men in their 20s and 30s lack simple manners.

They text after 9pm asking to go out.
They don’t open doors.
They show up late for dates.
They don’t plan dates ahead of time.
They ask you to “hang out” and consider it a date.
They don’t walk you to your car at the end of the night.

Men in their 40s and 50s know how to date. They know how to be a gentleman. They grew up before texting was a thing. They grew up during a time when husbands bought flowers weekly for their wives.

I don’t know whether it’s the “Me Too” era or lack of a strong male role-model, but many young men just don’t know how to be a gentleman. Date an older guy, and you’ll see the benefits of old-school dating.

3. You Know What You Are Getting Into When Dating an Older Man

Guys in their 20s and 30s are still figuring out who they are. They are growing their career and exploring what they want to be when they grow up. They may not work out every day, but they may have hot bodies thanks to testosterone. Binge drinking and too much sun may not have taken a toll on their bodies yet.

Then, many men hit 30 or 35, and they look suddenly change. They become boring. They become stuck in a mediocre job. It becomes obvious they drank too much in their 20s and got too much sun. They just look old, and lack a zest for life.

When you date an older man, you know exactly what you are getting. He’s settled in his career. If he exercises and eats well, he’ll likely continue to do so. If he looks good in his 40s, he’ll probably continue to look good. There won’t be any unexpected surprises when you date an older man. He’ll likely be the same person 10 years from now as he is today.

4. Men In Their 40s and 50s Are Flexible On Kids

It’s hard for us women. When we turn 30, we realize we better get hustling if we want kids. We are stepping into quick sand, and feel like we better find a guy to pump out babies – ASAP. Or, if you are like many of my girlfriends in your mid-to-late 30s, you change your mind about kids. You no longer want kids, and it’s a struggle to find a single man your age who feels the same.

I’ve been pleasantly surprised to find men in their late 40s and 50s who are very flexible on kids. If you want kids, you win. If you don’t want kids, you win.

If an older man loves you and wants to make you happy, he’ll want to give you what you want in life. He’ll be open to more kids. This is especially true if he loves kids. By his late 40s/early 50s, a man’s kids are likely in college and out of the house. He’s had a few years to live up the single life and is open to settling down again.

If you don’t want kids, you are in luck too. An older man has “been there – done that.” This means an older man can also be happy marrying a woman who doesn’t want kids.

5. One Benefit of Dating an Older Man? He Has More Money.

This sounds shallow, but it’s true. As you’ve advanced in your career, you’ve likely gotten a salary or title increase every 2-3 years, right? When you date older men, you get men with more work experience, which means a higher paycheck.

When dating an older man, you won’t have to worry about paying your portion of the check on a first date, or even a second date. If anything, you offering to pay may be offensive. An older man won’t be cheap. Forking over $5 for a coffee or $50 for dinner will seem like pennies to him.

6. Older Men Have Flexibility at Work – Which Means Travel, Hobbies, and More Time with You

An older man likely has flexibility at work. He can come and go as he pleases, as he’s built a reputation for delivering results. If he owns a business, he controls his work schedule and can take time off as desired.

How does this benefit you as a woman? It means that an older man is well-rounded and has more free time for his hobbies, and for you. He can take a day off for a fun weekend getaway. He can leave work Friday afternoon to play golf or tennis. He can take a long vacation and travel internationally.

When you date an older man, you’ll find someone that wants to travel the world and go on adventures. This will all be possible due to the man’s flexibility at work and higher salary.

7. An Older Man Knows What He Wants from Dating

There’s no bull-shit or games when dating an older man. He’s likely been divorced. He’s dated a lot. He’s been in at least one serious relationship. He’s honest and straight-forward.

I’ve found that older men are inquisitive beings that ask deep questions on a first date. They jump right to the point. They will ask you what you want in a long term relationship. And don’t worry. Older men will return the favor and tell you exactly what they want.

Should You Date an Older Men? Absolutely – Give It a Go.

There’s a quote by Jackie Kennedy:

“The first time you marry for love, the second for money, and the third for companionship.”

I disagree. With an older man, you can get love and babies, money and sex, and life-long friendship and companionship. Word of caution: Make sure the man isn’t emotionally unavailable or bad news.

Good luck dating ladies! Let me know what you think in the comments. I’d love to hear from you!