dating a younger man

Navigating the world of dating is tough enough if you’re 20-something. Dating in your 30’s or 40’s, however, brings new challenges. Society norms lean toward women dating older men as this has been acceptable for ages. What happens if you fancy dating a younger man?

Sure, there are advantages to dating a younger man. Younger men tend to be more adventurous, open to change, sexually outgoing and make a woman feel younger. On the surface, these reasons are good enough to give it a go, right? But how young is too young?

In my experience, the younger the man is in relation to your own age, the more difficult the relationship will be in the long run. As an older woman looking for a younger man, commitment may not be your goal. However, these pitfalls are still valid even if you’re just “having fun.” Dating a man five years younger may not pose too much of an issue. He is probably still able to relate to you in the same manner as a man of your own age.  However, dating a man 10 years younger or more, the difference in age can become glaringly apparent. Before dating someone significantly younger than you, consider these potential pitfalls.

1. No sense of direction

As a mature woman, you probably have your sh*t together. You have all basics including a car, a home, and a job. Maybe you’ve been married once or twice. With all that life experience, a sense of direction develops and the end-game becomes clear. We know what we want and where we are going with our lives.

At first, that young guy may seem exciting and carefree. Eventually, however, you probably realize he has NO idea what he is going to do with the rest of his life. If he is significantly younger, he may not even be done with college! Although a lack of direction isn’t a big deal in your 20’s, in your 40’s (or late 30’s) this seems dangerous and irresponsible. If you are looking for stability, you may not find it with a younger man.

At first, that young guy may seem exciting and carefree. Eventually, however, you probably realize he has NO idea what he is going to do with the rest of his life. Click To Tweet

2. Financial uncertainty

A lack of direction usually translates into job hopping or worse, no job at all. Younger guys haven’t always decided what they want to be when they grow up. I know this seems bitchy, but the sad truth is, at 40, being a broke college student doesn’t have much appeal. Been there, done that!

Every younger man isn’t broke, I understand that. However, their financial goals probably do not align with ours. As we get older, planning for retirement and investing wisely becomes a priority. At 20-something, making money and taking risks with our investments is fine because there is time for financial recovery.

3. Different ideas of the world

As a mature woman, you probably enjoy stimulating conversation over dinner or drinks. Depending on your age difference, this may be difficult for you both. Younger guys do not have the life experience yet and may not challenge your mind the way an older man could over dinner.

Most of the younger man’s knowledge will be based on college. Now I am all for deep, philosophical conversations. However, as many years have passed since my last philosophy class, my memory is a bit fuzzy on Nietzsche nor do I want to have a deep discussion about how he plays a part in my modern life. I just want to drink my cosmo, eat carbs and maybe grab a good night kiss!

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Differing ideas with your partner makes things interesting. In this, a younger man may seem like a breath of fresh air. I would agree, for a while. After a period of time, the gap between your idea of the world and his idea of the world will seem like the Grand Canyon. Our life experience shapes the way we see things in the world — good and bad. In general, young people still have rose-colored glasses regarding the world and how it all works.

Their views aren’t necessarily a bad thing. We need fresh, new ideas to make this world a better place. When it comes to our partner, however, huge differences in opinions tend to lead to discord in the relationship. Arguments are hard to avoid if your world views are decades apart.

I just want to drink my cosmo, eat carbs and maybe grab a good night kiss! Click To Tweet

4. His ever-shifting focus

You have to be supportive of him always trying new things. Even as I am writing, this doesn’t sound terrible. He loves adventure and always has a new project, right? Enthusiasm for his passions is infectious and you may find this very attractive at first. However, every week he has a new hobby, passion or interest, trying to keep up with his latest passion and be supportive is draining.

Mature women have their passions and interests, but we are not looking for a new one every week. Eventually, you will feel frustrated that your younger partner cannot commit to one interest and see it to the end.

5. Feeling like his mom

Young guys have a zest for life that their older counterparts may have somewhat lost. I think this is what makes younger men so appealing to so many older women. I found myself both loving and hating younger men’s exuberance. Yes, it was refreshing-except for when it wasn’t.

I found myself being condescending or even scolding if I thought their actions were dangerous or just immature. Scolding or lecturing your boyfriend never ends well and tends to put a damper on the romance. He will have a hard time thinking of you as his partner and lover if you criticize his choice to stay out until 3 am on a Wednesday.

Scolding or lecturing your boyfriend never ends well and tends to put a damper on the romance. Click To Tweet

6. His unnecessary risk-taking

Younger guys tend to have a predisposition to taking unnecessary risks. These could be physical or financial in nature. Either way, these risks play havoc with our need for stability. We are usually searching for stability and someone grounding rather than an off-the-cuff way of life.

Again, at first, it might seem exciting. Once our sense of well-being is threatened, the instances of acting like his mom grow exponentially. It’s a natural response to a threat to our future stability and is normal when dating someone with an opposite world view.

Combating this reaction will go against your basic survival instincts. At some point in the relationship, it will become apparent the risks outweigh the gains and you may need to make a hard decision. Evaluate your life goals before getting involved with someone significantly younger than you.

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7. His fear of commitment

Some of you may not want a commitment right now. I get that. I felt the same way when I first separated from my then-husband. As time went on and I got older, I realized having someone unstable in my life made my world chaotic. I craved the stability my marriage had afforded me and I wasn’t finding that trait in the younger guy.

What I needed was a commitment! Don’t get me wrong. Older men often have a fear of commitment too. Especially if they had or are in the midst of a bitter divorce. Luckily, older men know the safety of commitment too even if their marriages didn’t work out.

Younger guys aren’t thinking about their future with too much gusto. Depending on the age difference, they may even think they don’t want kids. I assume men run into this same issue dating younger women. One day, their biological clock will kick in and then what? If you are where I am, this sounds like a nightmare!

If you are going to venture out and date a young guy, take commitment off the table. Seriously, 20-somethings aren’t ready for commitment even if they think they do. I believe you are setting yourself up for heartache. Yes, there are instances when it works, however, disasters are way more common.

If you are going to venture out and date a young guy, take commitment off the table. Click To Tweet

8. Sexual incompatibility

Younger men bring in the bedroom their stamina and energy. I know what you’re thinking. Is there a downside to this? Ummm, yes! I know, ladies, you think I am crazy, but hear me out.

It’s 3 am on a Wednesday morning. You have an early meeting and a huge presentation at work the next day. Your man decides now is the perfect time for some lovemaking. Now, in theory, sounds like heaven, right? Ugh, no!

I get this is not the end of the world and I admit in the beginning it is very exciting to be woken up by a passionate man. In practice, this gets old and annoying. Yes, I said it! As older women, most of us don’t have the stamina for sex that a man in his 20s has and personally, I don’t need that.

Younger men definitely bring their A-game in the stamina department, but what about their skills? I think back to my 20s and remember the utter lack of orgasms. Unfortunately, what younger men bring to the bedroom in stamina, they tend to lack in experience. Older men just know their way around and are more worried about their own rather than of their partners’ orgasms.

9. His immaturity

I get that sometimes not acting our age is fun and give us a break from our real lives. This is another reason so many women gravitate toward younger men. I don’t know about you, but acting 20-something when my body is 40-something was demanding and draining.

Constantly trying to keep up while making it seem effortless is tiring in any aspect of your life. Imagine having to do it in your new relationship? I understand not every young guy will be immature or act childish. However, if you find yourself thinking he needs to grow up or scolding him, this may be a sign he is too young.

10. Socially awkward situations

Social standards stink sometimes and there is definitely a double standard when it comes to women dating younger men. With men, it seems socially acceptable even when the age difference is shocking, while when women date much younger men it is still considered socially awkward.

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Other women tend to be the biggest critics of these May-December connections. As a grown woman, I believe the choice is yours and your friends should be supportive. Unfortunately, you may be left out of social gatherings or events. Some may not feel comfortable or feel your partner isn’t mature enough for their event or dinner party. Often our friends have fully developed careers or businesses which may not yet be the case for your guy. Be prepared to answer the typical questions such as: “What does your boyfriend do?”, “What do you two have in common?” or remarks “He’s so young”.

Inherently, we want to protect our relationships. You may find yourself backing away from your friends and family due to their negativity about your new guy. Sometimes, even being around his friends can be awkward and they may not be too accepting of you. Your younger man may take some heat for dating an “old lady.”

Social standards stink sometimes and there is definitely a double standard when it comes to women dating younger men. Click To Tweet

11. The pressure to stay youthful

Women struggle their entire lives with self-confidence. Body shaming and the beauty industry create fear in women of being less-than. When dating younger men, women will struggle even more from the pressure to keep herself young and beautiful. The fear of “letting ourselves go” and losing our younger man can make us a little crazy.

Trying to live up to standards we can’t possibly attain may start a vicious cycle of self-loathing. Especially if the younger guy ends the relationship. I understand that insecurity can raise its head in all kinds of relationships. I also get that some of the women reading this won’t believe this is an issue for them. Their relationship is different and strong. Ok, great.

Any of the above pitfalls could be the one thing that triggers this sense of pressure to stay youthful. Almost every woman would agree that wrinkles and sagging suck! Regrettably, this pressure and the crazy that may manifest could be the downfall of the relationship.

Even with all these potential pitfalls, my advice would never be to steer clear from a man younger than you. Can it work? You bet. Might it fail? Yes, but so could any relationship. Simply remember these pitfalls when making the decision to date a younger man.

In no way am I implying that all these pitfalls will plague all older lady-younger man relationships. There are exceptions to every rule and frankly, there is no such thing as “rules” when it comes to love. As in any relationship we need to decide whether the pitfalls are worth the rewards. If the answer is yes, then you go girl! If the answer is no, then perhaps dating younger guys isn’t for you.

Connie is dating and relationship coach specializing in women over 40 who are looking for love. After finding herself single at 40 with 2 teenage children, she made every dating mistake possible. Now happily married, Connie is helping others to find the love of their lives. You can read her articles on her website CocktailsAndHotFlashes.com.


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