Red Flags When Dating An Older Man

Are you a young woman interested in dating an older man or already in a relationship with one? While there’s nothing wrong with this kind of relationship, there are certain challenges and potential red flags to be aware of.

But don’t let that discourage you! With the right mindset and communication, you can navigate these issues and have a fulfilling relationship. To help you out, here are some red flags when dating an older man.

1. He Is Unwilling To Apologize When Wrong.

When dating an older man, it may be concerning if they cannot utter the words “I’m sorry.” A successful relationship thrives on the ability of both parties to admit their faults, assume responsibility, and apologize when necessary.

However, establishing a lasting bond becomes unattainable when one refuses to acknowledge their mistakes or misconduct. Therefore, if their inability to apologize stems from their age, it should be considered a warning sign.

2. He Is Resistant To Change.

Change is an inevitable aspect of life, and it’s essential to recognize that it impacts us all, whether in a relationship or not.

Suppose your older partner is resistant to new experiences and prefers to maintain their routine, despite your efforts to encourage positive change. In that case, it may be time to reconsider your relationship.

If your partner fails to acknowledge personal growth or the need for it in your relationship, it may be challenging to maintain a healthy partnership.

It’s common for older men to resist change because they’re comfortable with their current lifestyle, and any alteration may disrupt their comfort.

However, a partner who truly loves you and isn’t too proud should be receptive to your perspective on life, as long as it’s not harmful.

3. He Always Tries To Gaslight You

Gaslighting occurs when someone causes you to question your perception of reality, leading you to doubt what you know to be true. Recognizing this as a red flag when starting a new relationship is crucial.

If your partner says they’ll do something and then does the opposite. When confronted, they deflect the issue back onto you or dismiss it as insignificant, and this behavior can make you feel like you’re losing your grip on reality.

Trust is a fundamental component of any relationship, and consistency is vital. If he promises to do something, you should be able to count on him to follow through, and if he can’t, he should acknowledge it and apologize.

The consistency between what someone says and what they do is critical in building trust within a relationship. Therefore, being wary of any partner who engages in gaslighting tactics is essential.

4. He Claims To Be Separated, Although He’s Still Married.

If you’re dating an older man who frequently uses the term “separated,” it’s essential to understand that he is still legally married.

Claiming to be separated while still legally married is one of a relationship’s most significant red flags. It’s possible that he’s lying to you or not entirely over his previous relationship.

Although there may be several reasons for this behavior, you should not be with someone who isn’t single. Therefore, it’s essential to approach such situations cautiously and avoid getting emotionally invested until you’re sure of the circumstances.

5. He Wants To Marry You Too Soon.

If an older man is pushing to get married immediately, it should be a cause for concern. While it’s natural to develop strong feelings for someone and envision a future together, rushing into marriage without laying a foundation for a healthy relationship can be a major red flag.

There are many potential reasons why an older man may be in a hurry to get married. Perhaps he’s seeking a quick fix for his loneliness or trying to cover up a questionable past.

Whatever the case, it’s important not to rush into anything without taking the time to truly get to know your partner and build a strong foundation.

Consider this: how can someone propose marriage after only a month or two of knowing you? The answer is that it’s not about you but rather something he’s not telling you.

Instead of jumping into a marriage proposal, take the time to ask questions and get to know him and his past relationships before making any big decisions.

6. He Has A Bitter Disposition Toward Love.

It’s common for older men to have emotional scars from past relationships, such as being cheated on, lied to, or manipulated by previous girlfriends or wives. Due to these negative experiences, they may hold a grudge against women and love.


If the older man you’re dating has these emotional wounds, expressing genuine love will be difficult for him unless he works on himself and heals.

It’s best to advise him to take the time to heal before pursuing a new relationship because he won’t be emotionally available for love. If he still holds anger and resentment towards his ex-wife or previous partners, he’ll likely have a negative attitude toward you.

So, paying attention to his past experiences and how he talks about them is essential to understand his emotional availability for a relationship.

7. He Suffers From Depression.

It’s important to be aware of the potential for depression and low self-esteem in older men for financial difficulties, homelessness, divorce, and a lack of purpose or direction in life. These factors should be considered potential red flags when dating an older man.

If your partner is consistently down or struggling with depression, it can be challenging to maintain a healthy relationship.

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

This is a major red flag in any relationship, but it especially concerns an older guy who has likely been through more and longer relationships.

If he’s still talking about his ex or if she’s still a big part of his life, there’s a chance he’s not over her.

This is a warning sign that you should take seriously, and it’s best to back off until he has it sorted out.

If he takes satisfaction in the attention he receives from his ex and frequently reaches out to her or gives her the liberty to access him at all times, it indicates that he still has feelings for her that must be addressed.

9. He Tries Comparing You With His Ex.

Comparing you to his ex is a major disrespect and a sign that he still has her in mind. Instead, he should concentrate on the present and making you feel special.

If your older man starts talking about his ex on your first date, it’s a warning sign. It becomes a bigger red flag if he starts comparing you to her later. Reflecting on past relationships is normal but unhealthy compared to the current one.

10. He Makes You Feel Embarrassed.

If you’re feeling ashamed because of your older partner, it might be a sign that something is wrong. Even if there’s an age difference, your partner should never embarrass you.

Older men may have more dating experience and be more confident in getting what they want, but this can sometimes lead to them crossing boundaries and making you feel uncomfortable or ashamed.

This behavior can take many forms, from making jokes at your expense to pressuring you into doing something you’re not ready for.

11. He Suffers From Peter Pan Syndrome.

Just because a man is older doesn’t mean he’s emotionally mature. Many men in their 40s still behave like they’re in their 20s and have yet to grow out of destructive behaviors and habits.

It’s important to watch for signs of Peter Pan syndrome when dating an older man. This condition is characterized by immaturity, irresponsibility, and selfishness.

Men with Peter Pan syndrome may struggle to form meaningful relationships and rely heavily on others for emotional support.

This can be a red flag that they need more time to be ready for the responsibilities of a serious relationship and may be unable to provide the support and stability they need.

12. See-Saw Effect

The “See-Saw Effect” refers to the balancing act of dating someone in midlife with other obligations like work and children.

While it’s important to respect their schedule, it’s also crucial to ensure that they prioritize the relationship.

Finding a balance is important if you’re in a serious relationship with an older man with other responsibilities.

It would help if you understood his schedule but also ensure you’re not constantly taking a backseat to other obligations. If you’re not being prioritized, it could be a red flag that the relationship could be more serious than you thought.

13. You Both Have Different Life Goals.

If your relationship is progressing, it’s important to discuss your future goals and plans. This includes starting a family, relocating, and supporting each other’s goals and happiness.

It’s crucial to ensure that both of your visions for the future align and that you’re both on the same page. This conversation can help avoid potential conflicts and ensure that you’re both moving forward in a mutually fulfilling way.

Remember that as you discuss your plans, you should be open and honest with each other about your goals and aspirations.

14. Having Different Sex Drives

Having different sex drives from your partner is a significant dating red flag. Maintaining a healthy sexual relationship is crucial, and having mismatched sex drives can make it challenging.

It’s important to keep the spark alive in any romantic relationship, and sex plays a vital role in achieving that.

Although your partner may be a great guy, having one partner constantly wanting more sex than the other can cause tension, frustration, resentment, insecurity, and even anger.

Therefore, it’s essential to address this issue and find a solution for both partners to avoid any long-term negative impacts on the relationship.

15. He Is Emotionally Unavailable.

If you’re dating an older man who is emotionally unavailable, it’s a red flag. Emotionally unavailable men can be hard to love as they often don’t show their feelings or allow you to get close to them.

This could be due to several reasons, such as not being over an ex or being afraid of getting hurt.

Observing negative attitudes towards ex-partners or women, in general, is important, as this may be a sign of emotional wounds.

Look for clues that he is working on himself and have a conversation with him to understand his emotional availability and whether he needs more time to heal.

16. He Becomes Controlling And Possessive

While being possessive can seem harmless, it can easily lead to an unhealthy relationship if not addressed.

Controlling behavior can take many forms, including dictating what you wear, who you hang out with, or where you go.

An older man may try to take the lead, but this can quickly turn into him trying to control your life, which is unacceptable and a major red flag. No matter how much he loves you, a man you’re dating should never control you.

17. He Treats You In A Derogatory Manner.

Although some older men may be nurturing and caring towards younger partners, it’s important to be aware that some may exploit their partner’s lack of experience and youthful naivety.

If he only treats you like a child and not others his age, it could indicate that he doesn’t respect your maturity or independence.

This behavior may stem from a superiority complex, a sign of underlying insecurity or a desire to control you. In either case, it’s a red flag, and you should consider running from the relationship.

Ultimately, it’s essential for your partner to trust and respect your decision-making abilities, regardless of age or experience.

18. He Has Commitment Issues.

It could be a sign of commitment issues if you’re ready to take your relationship to the next level, but your partner isn’t willing to commit. Perhaps he hasn’t healed from his previous relationship or has trust issues due to past hurts.

Investing only a little time and effort into someone who is not ready for a committed relationship is important. This won’t be fair to you or lead to a lasting and fulfilling relationship.

19. He Abuses Drugs And Drinks A Lot.

Frequent use of drugs and excessive drinking can indicate multiple problems, such as substance abuse, difficulty handling relationships or stress, and an unhealthy lifestyle.

If you are in a relationship with an older man who engages in these activities, it is crucial to take action.

These behaviors are often a result of desperation during tough times, but they can affect your mental health and overall well-being.

Staying in this kind of relationship will only make things worse over time. Remember, you cannot change someone who does not want to change.

It is not your responsibility to rehabilitate him. It is essential to prioritize your health and safety and seek help.

20. He Has Kids

While having children is perfectly acceptable, some women may not be ready for the responsibilities that come with it and may view it as a significant commitment.

If your partner is actively involved in parenting, he may have less time to spend with you due to the substantial amount of time, attention, and energy required to care for children.

Additionally, several potential issues may arise, which you may not initially consider, such as:

  • Your partner may be occupied when you want to spend time together, such as on weekends.
  • His children may not approve of or accept you.
  • He may not want to have children with you in the future.

Therefore, you should carefully consider how your partner having children may impact you and approach the situation thoughtfully, using your head rather than solely your heart.

21. He Is Not Interested In Knowing Your Friends And Family.

If you are dating an older man and he doesn’t make an effort to get to know your friends, it may indicate a potential problem.

He needs to show an interest in the people who matter to him and try to build relationships with them. It’s not uncommon for older men to feel like they have nothing in common with their friends or fear being judged by them.

Moreover, it’s even more concerning if the older man shows no interest in meeting your family. While you don’t necessarily need their approval, it’s natural to want your loved ones to like the person you’re dating.

While meeting family members can be daunting, he should still try to connect with them, at least to some extent. If he refuses, it’s a cause for concern, and you should proceed cautiously.

22. He Refrains From Introducing You To His Family And Friends.

If your partner is hesitant to introduce you to his friends and family, it’s a warning sign that should not be ignored.

While there may be various reasons for this behavior, it’s often an indication that he’s not genuinely interested in the relationship or is hiding something from you.

It’s crucial to address this issue with him and express your concerns. If it’s not a significant matter, he should be able to come up with a resolution promptly. However, if he continues to avoid introducing you to the important people in his life, it may be time to reevaluate the relationship.

23. He Normalizes Flirting With Other Women In Your Presence.

When an older man comes out of a long-term relationship and finds himself single, he may not be accustomed to flirting or view it as harmless fun.

Nonetheless, if he engages in this behavior in your presence, it should be considered a warning sign.

It indicates a lack of respect for you if he is willing to flirt with other women openly in front of you. He may be relishing his newfound freedom too much following his marriage.

What Are The Reasons For Individuals Disregarding Red Flags In Romantic Relationships?

It’s crucial to take heed of the red flags mentioned above when others display them. Refrain from dismissing them outright.

Loving someone without expecting anything in return can lead to unreciprocated affection, wherein you adore someone unsuitable for your life, who ignores you, or fails to invest in the relationship. It’s a calamity, a misplaced generosity.

When an individual discloses their negative qualities or shows that they’re mean, selfish, or unkind, it’s imperative not to ignore them. They’re informing and demonstrating something about themselves, and we should presume they have no reason to deceive us.

So, why do we disregard it when people exhibit their true selves? It’s due to the notion that our duty when we love someone is to attempt to fix them.

We overlook the red flags because we see the best in them. However, we don’t have just one role in life. Expressing love or demonstrating it is only one aspect of our responsibilities. Our other job is to safeguard ourselves.

When We Notice Red Flags, How Do We Deal With Them?

The boxing referee’s famous line “protect yourself at all times” is a lesson that can be applied to relationships. In love, no referee stops the fight when one person can no longer protect themselves.

It is important to be both the fighter and the referee and to recognize when it’s time to remove yourself from a harmful situation.

On a related note, it’s important to be aware of red flags, such as anger issues and commitment problems, when dating an older man. Still, it can also be an opportunity to learn from someone with more life experience.


In conclusion, dating an older man has advantages and disadvantages. While some women may find the stability and maturity of an older partner appealing, there are certain red flags when dating an older man that should not be ignored.

These may include controlling behavior, an unwillingness to compromise, and a large age gap that can create power imbalances in the relationship.

It’s important to trust your instincts and not dismiss warning signs in the early stages of a relationship.

Remember, a healthy relationship is built on trust, mutual respect, and open communication. By being aware of the red flags when dating an older man, you can make a more informed decision about whether this type of relationship is right for you.


Leave a Reply

Your email address will not be published. Required fields are marked *