It's possible you've been toying with the idea of dating a younger man. Fabulous! There's quite a large pool of these men looking to meet you.

If you'd like to find a younger man who's looking to date an older woman locally near you, I'd suggest creating a free profile on Older Women Dating (go directly to site here), OR you can read my full review of it first. It's the best cougar/cub platform I could find currently available.

Now, there's a question I need to ask you…

How can you help a younger man build confidence while dating him?

1. Embrace His Energy.

2. Manage The Fantasy.

3. Coach Them Up.

4. Bring Them Around Friends.

5. Let Him Provide Sometimes.

6. Be Aware Of The Power Dynamic.

7. Don’t Freak Out About Him Playing Games.

8. Hear Him Out.

9. Dress Him Up.

10. Be Brutally Honest.

Dating a younger man is different from seeing someone your own age. People are going through different life phases and have differing priorities.

While it can be a fantasy that some men toy with, they can also struggle with confidence issues.

Here are these ten helpful tips, in detail, to dating a younger man so he’ll stay secure in the relationship with you:

2 guy at a spartan race

1. Embrace His Energy

If you’ve made it into middle age, you’re probably over the club scene. A three-night bender in Vegas isn’t your cup of tea anymore…

And no, you don’t like the idea of adventure camping in the Rockies…

Energy gaps in couples is a major issue women face when dating a younger man. When men are in their twenties, they still have a lot of youthful exuberance.

They aren’t selective in their ambitions because they have enough juice to attack them all at the same time.

Whether it’s a passion for exercising, travel, or partying, the demands can put a lot of pressure on a relationship if the female partner doesn’t play along.

The key is to reach a compromise.

You don’t have to tag along to every concert or late-night movie, but don’t slow him down if he wants to go himself with friends.

You don’t have to be at every Spartan Race he enters, but maybe try one or two to show him some support.

The most important thing women can do is validate their energy and offer encouragement.

Play along as much as you can. It will help keep you feeling young.

3 older woman leans into young man

2. Manage The Fantasy

For whatever reason, some men idealize being with an older woman. Who cares, really, as long as it’s not some sort of unhealthy fetish.

Some men struggle with the pressure of shouldering so much responsibility in relationships.

Older women are often assumed to be more put together.

They have self-supporting careers, are generally believed to be less emotionally volatile, and, sure, maybe know a thing or two more in the bedroom.

Nevertheless, it’s important that women don’t overindulge fantasies. It’s not conducive to healthy long-term relationships.

It’s perfectly alright to feel flattered that a young attractive male finds you sexy. You just don’t want there to be misperceptions about why you’re together.

You need to manage the relationship so that both of you are acting as co-equal partners.

Otherwise, you’ll eventually end up feeling like you’re carrying dead weight around.

He won’t stimulate you the way you need to be in order to feel happy.

younger man older woman on the beach smiling

3. Coach Them Up

Older people, men and women, are more set in their ways. It’s not because they refuse to change, but more because they’ve lived through more and know what they want.

They don’t want to waste their time pursuing things that don’t fulfill them.

Younger men often lack this life experience through no fault of their own. Older women shouldn’t rob them of these valuable experiences.

However, older partners are great because they can give pertinent advice. For example, many young men struggle with finding purpose in their careers.

Older women who’ve seen some levels of professional success can help guide them and think through these types of issues.

They can coach them on how to get ahead and develop passions. Women can also coach men through rough patches in a relationship.

Sometimes dating a younger man means you’ll struggle with their insecurities, their lack of compassion, or other insensitivities.

These are usually just part of being young. Older women who are able to navigate these issues because of their experience can keep things progressing smoothly.

He’ll feel confident knowing that despite his ups or downs, you’re there for him.

Older women can excel at being a supportive lover and friend.

5 older women dancing with young guy

4. Bring Him Around Friends

It’s easy for younger men to feel insecure when dating an older woman who’s put together.

They might not have as high-paying a job or might not even be in their own place yet.

They’re still getting started in life. That’s nothing to be ashamed of.

Sometimes when there’s a significant age gap, the younger partner can feel like they don’t know how to define things in the relationship.

They might be worried that they are just a fling you’re having a good time with and nothing more.

The best thing you can do to give him confidence is flout him around town like he’s the best you’ve ever had.

Introduce him to friends and bring him to a family dinner. Introduce him at work functions as your boyfriend.

It’ll give him the reassurance he needs to know he’s not a passing phase.

He might feel awkward hanging around an older crowd at first, especially if you’re in a different socio-economic demographic, but he’ll adapt.

6 dating a younger man paying the bill

5. Let Him Provide Sometimes

You might think it’s cute or silly to have him pick up the tab, but allowing him to provide is a key component of dating these younger men.

More women are going to universities than men, and more and more women are taking on high-paying executive roles in the workplace.

While it might have been a thorny issue to have a wife out-earn a husband decades ago, that shouldn’t be a problem in any modern marriage or relationship.

Most men these days are pumped if their female partner earns more money.

Besides, who would want to waste time being with someone who gets caught up over your success.

Earning more doesn’t mean that you have to pay for everything, though.

Younger men will feel some insecurity over their financial situation if you’ve got a nice house, car and some other finer things in life.

It’s not that they feel ashamed, but they want to be an equal partner in the relationship.

Letting him pick up tab at dinner or taking on the phone bill payment as things get more serious are great ways to show him respect.

7 rich woman on a private plane

6. Be Aware Of The Power Dynamic

Women need to understand that dating a younger man means things will change as they mature.

Think about how you evolved from who you were in your early twenties into who you are now.

You want different things, you probably have shifted in your political views, and you’re less willing to cede control to others.

It may seem fun at first when a younger guy takes a back seat and lets you make most of the decisions.

Just be aware that as he gets older and experiences more success in his career or education, that he will be more interested in asserting himself as well.

You need to be able to create space for him to feel confident as a copilot.

8 young guy depressed under a tree

7. Don’t Freak Out About Him Playing Games

Young guys get jealous more often. They’re not as good at communicating feelings.

They aren’t as attuned to what makes women tick and how to be sensitive to your needs.

This is part of the younger man package that women will have to deal with.

Younger people, to a certain extent, love the drama that comes with relationships. Stability can feel boring, and boring often spells trouble to them.

They might feel like things are getting stale, that you’re tired of them, so they’ll do something dramatic to spice things up.

Don’t let it catch you off guard. Reaffirm your feelings with him and explain your approach to things.

Helping see how you perceive these types of games will help him grow out of them faster.

9 sad young guy with hand on his face

8. Hear Him Out

A lot of the time, older women want to give answers to life’s problems before their younger partner has even finished explaining them.

It’s a common pitfall to offer solutions and try to fix difficulties they’re going through when all they want is to be heard.

Older women need to remind themselves not to rob their younger partners of valuable life experiences.

Things like managing family conflict and professional development typically take going through them to figure things out.

It’s something they’ve got to live through themselves. That doesn’t mean, though, that he won’t want to talk it through with you.

In fact, you’ll likely hear all about it. Just remember to hold back giving too much advice.

Older women only need to offer support and be present in order to make men feel confident.

10 dating a younger man dressing up in a suit

9. Dress Him Up

This is a simple thing that can actually have a big impact.

One of the best things about an older woman dating a younger man is that they can help them with personal style.

It often takes a decade after college for men to embrace fitted clothing and nice suits.

A ton of young guys look thrown together in their twenties. An older woman guiding him in fashion choices can make him feel more confident about his appearance.

That will have a real impact on pushing his career forward as well. Tell him to spend a little extra on the high-quality shoes that will last forever.

Put on a subtle elegant cologne and ditch those t-shirts he got for signing up for a credit card.

Older women can help younger men focus on style that holds value and stay away from short-lived trends.

It will elevate his game and his confidence will bleed into other aspects of his life.

11 older woman on a cell phone

10. Be Brutally Honest

Young men can struggle with direction. Many report feeling lost at some point in their life or career.

A lot of men wish they had a mentor that they could lean on for advice and guidance. As an older woman, you can be that mentor to him while you’re together.

You can be there to give advice on how to handle job options, whether to go back to school or not, or how to resolve personal conflicts.

Your words will carry extra weight because you’re an example of someone who’s been through and made it to the other side.

Women need to be careful, though, that any advice they offer is given from a place of love and positivity.

It’s easy for men to feel like you’re coming down hard on them.

Even though you might feel like you’re on an equal playing field in your relationship, negative criticism can be taken the wrong way.

If you’re a successful lawyer and you tell him you don’t think law school is right for him, he might receive it as being harsh or demeaning.

It’s a difficult balance, but it can be done by being there as a mentor and supporting his positive ambitions.

**Again, if you'd like to find a younger man who's looking to date an older woman locally near you, create a free profile on Older Women Dating (go directly to site here), OR you can read my full review of it first.


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