Skip to Content

When a Man Keeps Cheating with the Same Woman for Years: 14 Things It Means

When a Man Keeps Cheating with the Same Woman for Years: 14 Things It Means

Sharing is caring!

For a lot of people, cheating is a one-time mistake that can be forgiven and moved on from.

However, when a man keeps cheating with the same woman for years, hmmm, there is more to it.

If you’re dealing with a situation like this, it might help to understand why this behavior is happening.

When a man keeps cheating with the same woman for years, let’s see what it means:

When a Man Keeps Cheating with the Same Woman for Years: 14 Things It Means

1. He Has an Emotional Connection With Her

When a Man Keeps Cheating with the Same Woman for Years

First up, if a man is cheating with the same woman for years, there’s a chance he’s emotionally connected with her.

It’s not just a fling or about physical attraction; this is a long-term affair we’re talking about.

The duration alone suggests that there might be an emotional element to the affair.

This emotional connection could be based on friendship, interests, emotional support, inside jokes, personal stories, dreams, fears, or even love.

You know, the elements that often form the backbone of an emotional connection.

So, it’s like they have their private world.

It’s different from a random fling because there’s a layer of emotional intimacy that keeps pulling him back to her.

If it was just about sex or the thrill of cheating, he might have moved on to someone else by now, but he hasn’t.


E for emotional connection.

Emotional cheating is, for many people, even more devastating than a one-night stand.

Understanding the emotional angle doesn’t make it okay, but it gives us a deeper insight into what’s happening.


2. He Feels a Sense of Loyalty to Her

Another reason why a man might keep cheating with the same woman for years is that he feels a sense of loyalty to her.

This could be due to past history, experiences they shared together, or even guilt.

Maybe she was there for him during a difficult time in his life or helped him through tough decisions.

He may feel indebted to her and unable to completely cut ties, leading him to continue the affair.


3. It’s Convenient

When a Man Keeps Cheating with the Same Woman for Years

Yeah, sometimes it’s just that simple.

If the other woman is always available and willing, it’s easier to keep going back to her rather than finding someone new.

It’s like taking the path of least resistance.

If he’s able to keep the affair under wraps and doesn’t have to deal with any drama or consequences, why would he want to stop?


4. He Doesn’t Want to Let Her Go

Sometimes, a man may have genuine feelings for both his partner and the person he’s cheating with.

He may not want to let either go and struggles with the idea of losing either one.

So, he chooses to keep both relationships going, hoping he can have his cake and eat it, too.

This is especially true if you’ve caught him many times with the same woman over and over again.

And even after threatening to leave him or him promising to break it off, he just can’t seem to stay away from her.

It’s obvious he doesn’t want to let go of her.


5. They Have a Mutual Understanding

See, the other woman may also be in a committed relationship and might understand the arrangement.

They may agree to just have fun or support each other without any expectations of leaving their respective partners.

This mutual understanding allows the man to continue cheating without any guilt or consequences, making it easier for him to keep going back to her.


6. He Has Commitment Issues

Commitment issues can manifest in many ways, and one of them is through infidelity.

A man may not want to fully commit to one person and might feel safer having a backup option in case the current relationship doesn’t work out.

This can lead to long-term affairs with the same woman, as he may feel more comfortable with her and their arrangement.


7. He’s Addicted to the Thrill

When a Man Keeps Cheating with the Same Woman for Years

Some people are addicted to the thrill and excitement of cheating.

So, it’s not about the other person per se, but rather the adrenaline rush they get from sneaking around and engaging in risky behavior.

The sneaking around, the lies, and the risk of getting caught can be a huge adrenaline rush.

Have you noticed that sometimes, the other woman is not even as attractive or compatible as his partner?

It’s not always about the person; it’s about the thrill of the affair.

For men who are addicted to this thrill, they may keep going back to the same woman as it satisfies their need for adventure and danger.


8. He Has Low Self-Esteem

Another possible reason why a man may continue cheating with the same woman for years is because he has low self-esteem.

He may feel unworthy or unlovable and seek validation from multiple sources, including the other woman.

The constant attention and affection she gives him boosts his self-worth and feeds into his ego, making it difficult for him to end the affair.


9. He Feels Like He Can’t Get Out

Sometimes, a man may feel trapped in an affair that has gone on for years with the same woman.

He may have tried to end things multiple times but keeps going back to her due to various reasons, such as fear of losing her, fear of change, or fear of being alone.

Or perhaps she’s using emotional blackmail to keep him coming back.

In any case, he may feel like he can’t get out and is stuck in a cycle of cheating with the same woman.


10. He Likes the Feeling of Being Wanted by Two Women

When a Man Keeps Cheating with the Same Woman for Years

For some men, the idea of having two women who desire them and want to be with them is an ego boost.

In this case, the man may continue to cheat with the same woman because he enjoys feeling wanted by two women at once.

It gives him a sense of power and control, which could be addictive for some individuals.

That’s greedy, if you ask me.


11. He’s Avoiding Dealing With Issues in His Relationship

When a Man Keeps Cheating with the Same Woman for Years

Cheating is often a way for individuals to avoid facing and dealing with issues in their relationships.

By engaging in an affair, he may feel like he’s escaping from the problems and conflicts in his current relationship.

However, this doesn’t solve anything and instead further complicates things.

The man may not have the emotional maturity or willingness to address the underlying issues in his relationship, causing him to continue cheating with the same woman.


12. He Feels Like He Can’t Get Caught

If a man has been cheating with the same woman for years, he may feel like he can’t get caught.

He may have become skilled at covering his tracks or developed a system in which he can easily deceive his partner.

This sense of invincibility may lead him to continue the affair without fear of getting caught.


13. He’s Unhappy in His Relationship

A man who continues to cheat with the same woman for years may be unhappy in his current relationship/marriage.

He may feel unfulfilled emotionally or physically and use the affair as a way to fill those voids.

These feelings of dissatisfaction may have been present before the affair started, and he may continue to cheat as a means of coping with his unhappiness.


14. He’s Not Ready to Face the Consequences

Lastly, a man may keep cheating with the same woman because he’s not ready to face the consequences of ending it.

This could include hurting his partner, losing her trust, or even losing her altogether.

He may not be ready to deal with the fallout and would rather continue the affair than face these difficult consequences.

So, instead of ending things, he keeps going back to the other woman, hoping that nothing will change or come out in the open.


As you now realize, when a man continues to cheat with the same woman for years in a committed relationship/marriage, it’s usually not just about physical attraction or a lack of self-control.

There are often underlying reasons at play.

If you find yourself in a situation like this, I can’t imagine how damaging and traumatic it must be for you.

It’s easier to forgive cheating if it’s a one-time incident, but when it continues for years, it becomes a pattern of behavior that is much harder to forgive and move on from because it’s more than a simple mistake.

It’s a deliberate choice that has been made repeatedly, and it shows a lack of respect for the relationship, for you, and for himself.

In this situation, I encourage you to prioritize your self-respect and worth.

You deserve someone who will be faithful and committed to you, not someone who continues to cheat with the same woman for years while stringing you along.

Don’t let anyone make you feel like you have to tolerate infidelity or disrespect.

Your dreams and goals should always be your top priority, and a relationship should be an addition to your life, not the sole purpose of it.

You are capable of achieving great things and don’t need a man who can’t commit to hold you back.

You might want to consider getting professional advice or counseling, either alone or as a couple.

Take steps to protect your emotional and physical well-being.

And hey, don’t forget to reach out to friends and loved ones for support.

You don’t have to go through this alone.

I’m rooting for you!

Sharing is caring!


Wednesday 31st of January 2024

Sometimes it's when a good person is in a toxic relationship and feels he cannot discard his toxic partner because of her vulnerability and dependency, but his own needs are not being met.


Tuesday 21st of November 2023

Hi there Reading this article is like you have actually read my emotions. I thank you very much because I felt like I am not alone who is dealing with pain like this.

Mabel's Blog

Tuesday 21st of November 2023

Giving you hugs from here.