Red Flags When Dating An Older Man

17 Shocking Red Flags When Dating An Older Man

Are you a young woman dating an older man?

Or perhaps, you’re considering dating an older man or have even started to fall for him.

Honestly, there’s nothing wrong with a young woman dating an older man – even if you’re dating an older man in your 20s.

The most important thing is that you both love and make each other happy.

However, dating older men comes with its own challenges.

For example, there are dating red flags in men. But there are also certain red flags when dating an older man.

Maybe you’re wondering what you should look for regarding red flags.

You’re not alone because women always ask me how to spot red flags when dating an older man.  

The truth is, red flags come with dating older men.

And more often than not, these red flags are right in front of our eyes – but we choose to ignore them.

Maya Angelou once said, “When people show you who they are, believe them because they know themselves much better than you do.”

Recognizing red flags in dating isn’t always easy. Is it?

But don’t worry, there’re tips on dating an older man that can make the work easier for you.

So, in this article, I’ll explain why we ignore red flags and how you should respond when the warning signs appear.

But more importantly, I’ll show you red flags when dating an older man you should never ignore.

17 Red Flags When Dating An Older Man You Shouldn’t Ignore

1. Unapologetic

dating a separated man red flags

Perhaps one of the red flags to look out for when dating an older man is when they can’t say “I’m sorry.”

There’s a pride and ego that comes with being older.

So, they see apologizing to you as a turn-off even when they’ve offended you in the relationship.

I believe there’s great hope for a relationship between two people who can acknowledge wrongs, take responsibility, and apologize for them.

You can build on mistakes, provided you’re willing to take responsibility for them.

But when they’re unwilling to acknowledge that they did something wrong or acted poorly or selfishly, it becomes impossible to build something sustainable.

You know, respect is what we need in our relationships.

And having humility and showing up with that is so vital in building a solid relationship.

So, when they can’t say sorry because they’re older than you, that’s definitely a red flag to look out for.

2. Resistance To Change

This is kind of like piggy-backing off of the first point, but the closed-off-ness to change.

When dating someone with this mentality of “take me or leave me. This is who I am… don’t try to change me.”

This type of perspective can be such a massive red flag because when they can’t see that we’re all flawed in some way,

There’s always room to grow…and then they’re resistant to the idea of change.

This mindset makes it difficult to be in a relationship with somebody like that.

It seems like older men have done the deep work to improve themselves over time, but certainly not all of them.

Many out there are still in the habit of resisting change.

3. He Gaslights You

Gaslighting is when someone makes you question your reality and confuse you about what you know to be true.

This is a red flag not to ignore when dating someone new.

And like young people, some older men dating younger women do it.

They say they’re going to do one thing, and they do something completely different.

And when you confront them about it, they have this way of flipping it back on you or making you feel like you’re making a big deal out of nothing.

Honestly, this can start to make you feel like you’re losing your mind in the relationship.

For me, I think the entire basis for a relationship is trust.

When I say I’m going to do something, you can trust I’m going to do it.

Or, for the very least, if I don’t do it, I acknowledge that I haven’t done it. I won’t pretend I never said that in the first place.

Or, if it turns out that I forget, I apologize.

So, the consistency between what they say they’re going to do and then doing it is huge to any relationship and the trust built within it.

4. When He Uses The Word “Separated”

When you’re dating an older man who keeps using the word “separated,” it means he’s still legally married.

Don’t let him deceive you.

And if you’re looking for something long-term, maybe getting married,

I’d advise you shouldn’t get your hopes up…yet, unless you’re comfortable being a second wife.

Otherwise, be mindful of your dealings with him.


Because most of these older men don’t tell you all you need to know.

They hoard information from you to get you into dating them or even getting married to them.

You must protect your heart at all times.

Pay careful attention to the words he uses.

5. He Wants To Get Married ASAP

tips for dating an older man

As I mentioned, most of these older men don’t give you enough information about themselves to help you make a quality decision.

That’s why you have to be discerning, especially when your biological clock is ticking and you’re also desperate about getting married to any man available.

Being desperate is one of the signs you’re rushing into marriage.

They can take advantage of your desperation.

Is he asking you to marry him ASAP? If so, that’s a red flag you shouldn’t ignore.

Some of these men are married with kids but will never tell you about their past.

Many even have wives and kids oversee but will never tell you.

It would help if you found out more about him.

Think about it for a moment:

How can you meet someone, and within a month or two, he’s already planning to get married to you – without even knowing you that much?

The answer is simple.

It has nothing to do with you. It’s about him. There’s something he isn’t telling you.

So, instead of blindly falling for him and agreeing to his proposal, you should get to know him. Ask him questions about himself and his previous love life.

6. He Has A Negative Attitude Toward Love

You know the old saying, “Have been there, done that.”

In other words, you’ve seen it all.

You see, many of these older men have been emotionally wounded,

Either by previous girlfriends or even wives. And as a result, they tend to have a negative attitude toward women and love.

Perhaps, the older man you’re dating has been cheated on, lied to, and manipulated in the past. So there’s this resentment, bitterness, and anger bottled up inside of him.

It’s almost impossible for a man who feels these negative emotions to genuinely express love to you – unless he works on himself.

In fact, you should advise him to take his time to heal instead of finding love because he won’t be emotionally available for love.

What does he say about his previous wife (if any)?

What does he say about his exes?

If he still hates them and is angry about how they treated him, chances are you’re going to be at the receiving end of his negative feelings and attitude.

Watch out!

7. He’s Depressed

dating older men psychology

Perhaps, not too many women are aware of this.

Many older men are depressed or suffer low self-esteem, which can happen for several reasons.

It could be because he’s broke, homeless, divorced, or lacks purpose and meaning. He’s confused about life, and he’s stuck.

This is one dating red flags checklist you should take into consideration.

Dating a guy that’s depressed is difficult unless it’s something you’re up for. Otherwise, I suggest you look somewhere else.

8. He’s Still Emotionally Attached To His Wife Or Ex.

Many women say, “My boyfriend has no boundaries with his ex-wife”

Or, “my boyfriend won’t set boundaries with ex-wife.”

Or, “my boyfriend still messages his ex almost every day, and he says they’re just friends.”

You experience things like this because your boyfriend is still emotionally attached to his wife or ex.

Granted, I’m not suggesting in any way that he should become an enemy to his ex.

But healthy boundaries should be created to put them in their place.

But when a guy enjoys the attention he gets from his ex,

Either by constantly contacting them or allowing them to contact him,

It only suggests there is still an underlying emotional current he needs to address.

9. Make You Feel Embarrassed.

Let’s say you’re feeling insecure and express yourself to the man you’re dating…

Suppose he makes you feel embarrassed, ashamed and judged. In that case,

That’s challenging because the hardest thing in a relationship is to be vulnerable and feel safe about it.

When your vulnerability isn’t rewarded but rather punished, it becomes tough to get back from.

You find yourself shutting down and departing from your authentic self.

The trouble is, when we’re in a relationship, proximity is power.

When someone is really close to us, they have great influence on what we think, feel, and believe.

10. Peter Pan Syndrome

Emotional maturity doesn’t always correspond with age.

There’re a lot of older men in their 40s that are trapped in a 20-something-year-old body.

They remain stuck in destructive behaviors and habits from their youth.

For example:

Suppose they gaslight and guilt trip you, are reckless in their spending habit,

Can’t clean up after themselves, and don’t take responsibility for their mistakes.

In that case, you’re dating an emotionally immature boyfriend.

11. The See-Saw Effect

What does this mean?

Let’s say you’re dating a man in his 40s with kids.

Of course, you should know that dating in midlife requires a lot of balance…especially with kids, work, and other obligations pulling at his time.

If you’re in a serious relationship, you should respect his schedule, but not to the point where he doesn’t prioritize you.

 Not being prioritized in a relationship is a red flag you shouldn’t ignore.

12. He’s Blameless

Are you dating an older man who doesn’t seem to have contributed to his failed marriage or relationship?

Nothing is ever his fault. He blames his ex-wife or girlfriends for everything.

One of the hardest things in life is accepting responsibility, yet doing so is essential if you want to advance.

If not, your boyfriend might eventually start blaming you as well.

13. Does Your Vision For The Future Match Up?

While choosing engagement and wedding rings may not be on your two minds right now, it may be a good idea to have this conversation if things develop into something more serious.

Do you have any plans for your family?

Are you willing to relocate or travel?

Make sure you’ve talked about crucial topics like whether you both want children and whether you can support each other’s goals,

And the things that bring you both joy and happiness.

The truth is, he may feel as though his ambitions are coming to an end, while yours is just taking off.

14. Difference In Communication Style

In some cases, this might not be true. But it depends on who you’re seeing.

An older man could prefer a phone call over a series of texts.

A friend found remarkably slight distinctions in communication styles between people in their 30s, 50s, and 70s from his experience running a dating service.

Although people from the 90s are using it already, not all are open to technology and online dating.

15. Difference In Sex Drive

There is always someone who desires more or less sex in every relationship, regardless of age. But with significant age gaps, that can become even more obvious.

An older man has a more mature body, which might often be less energetic and have different sexual desires.

However, you may also resolve this by openly discussing sex and whether your needs are being satisfied. It’s just a difficult conversation; it’s not a deal breaker.

Frequently Asked Questions

Why Do People Ignore Red Flags In Romantic Relationships?

Believe them when people show you one or some of these red flags mentioned above. Don’t try to wave it off.

If you love someone without expectations, that’s a recipe for unrequited love…where you can love someone who isn’t suitable for your life, or he’s ignoring you or isn’t investing back.

That’s a disaster. A misappropriated generosity

And when someone tells or shows you “I’m a mean person. I’m selfish and unkind,” and you ignore it that’s on you.

Because they’re telling and showing us something about themselves, and we have to assume they have no reason whatsoever to lie.

So, why do we never listen to people when they show us who they are?

Well, it is this idea that our job when we love someone is to try and fix them.

That’s ignoring red flags because you see the best in them.

But we don’t just have one job in life. Loving someone or showing or giving love is just one of our jobs. The other job is to protect ourselves.

How To Deal With Red Flags In A Relationship.

In the boxing ring, what does the referee says to the boxers at the beginning of every fight?

In every boxing match, all the referees use the same line.

I know you probably don’t watch boxing, so I’ll tell you.

Referees look at both boxers and say, “protect yourself at all times.”

And at a certain point in the fight,

When the referee determines that one of the boxers is no longer capable of protecting themselves because

They’re punch drunk or not putting their arms up anymore and not guarding punches…

They are just taking a beating that’s putting them in genuine danger that could cause serious long-term harm,

the referee stops the fight.

The problem in love is that there’s no referee…that comes along to stop the fight if you’re no longer protecting yourself.

Your job is to be that referee. Your job is to be both the fighter and the referee.

And if you ever get to the point where you realize that you’re just taking a beating – emotionally,

Psychologically, and all, your job is to stop the fight and remove yourself from the ring.

Unfortunately, most people don’t stop.

They ignore what they know about someone, ignore how someone makes them feel,

And keep in the ring with that person taking punches that disfigure their hearts, soul, and mind.

They forget they have two jobs and not just one.

One job is to go out and love in the world, and the other is to protect yourself at all times.

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