13 Red Flags When Dating An Older Man

As someone who has always fancied the idea of an older partner, trust me when I say I get the appeal. The maturity, the slight brooding, worldly wise vibe, the confidence, and, oh, that salt-pepper hair. Older men have a lot going for them that can make any woman weak in the knees. However, there are two sides to every coin. You mustn’t let the charm and enigma blind you to the red flags when dating an older man.  

Older men have flaws, quirks, and shortcomings like any other human being. Add to the mix the emotional baggage or even unresolved trauma from the past, and dating older men can mean setting yourself up for complications. This is not to say that you shouldn’t pursue a romantic connection just because there’s a significant age gap.

However, it’s equally important not to place the man you’re dating on a pedestal just because he is older and wiser, as it may lead to you ignoring red flags early on and then finding yourself embroiled in a complicated relationship. If you’re already too emotionally invested by then, breaking free can mean putting yourself through the pain of heartbreak. To make sure that doesn’t happen, I’ve put together this checklist of red flags in a relationship with a man who is significantly older than you.

13 Red Flags When Dating An Older Man You Shouldn’t Overlook

When you like someone a lot, it’s easy to overlook red flags on a date or even in the early stages of dating. You see something that bothers you, but you don’t want to ruffle any feathers or spoil a good thing you’ve going on, so you tell yourself it’s not a big deal. If you have to do this often enough when dating an older man, know that you’re dealing with problematic behavior patterns and not just minor irritants that you can simply ignore.

Sooner or later, these relationship red flags will take a toll. Just as they did for Kathy and Mark. Kathy was 28 when she met Mark, 48, through mutual friends. Despite the 20-year age gap, they quickly bonded over shared interests in art and travel. Kathy was attracted to Mark’s confidence, life experience, and the stability he brought to her life. Mark, a successful business owner, appreciated Kathy’s youthful energy and creativity, which he felt was missing in his past relationships.

After two years of dating, Kathy began to feel overwhelmed by the red flags she had initially overlooked. The power imbalance, unresolved emotional baggage, lifestyle differences, and Mark’s growing insecurities made her question whether the relationship was sustainable. Despite loving Mark, she realized that their age gap created fundamental incompatibilities. After much reflection, Kathy decided to end the relationship. The breakup was difficult, and she still isn’t ready to let someone else into her life.

To make sure you don’t have to suffer similar consequences of dating an older man, you need to go in with your ears and eyes wide open. Be watchful of these 13 red flags when dating an older man:

1. Control issues

One of the oft-reported issues with dating older men is that they tend to exert control in the relationship, using their age or experience to make decisions on your behalf, limiting your independence. However, just because the person you’re dating is older does not mean that you should hand over the reins of your life to him nor should he expect you to.

If you’ve noticed that your man says things like, “Just trust me, I only want what’s best for you,” “I’ve been where you are, so I know exactly what you should do,” or “Don’t worry about it, I took care of it for you,” to deny you your agency, it’s one of the red flags you should ignore. Explaining why a need for control is dangerous, psychiatrist Dr. Laura Dabney says, “Control in relationships often stems from insecurities. It’s important to maintain autonomy while building a healthy connection.”

Related Reading: 11 Red Flags When Dating In Your 60s | DON’T Ignore These

2. Emotional baggage

Another one of the red flags when dating an older man is the unresolved emotional baggage from their past relationships, including divorces or strained family ties, that can impact the new relationship. My uncle, Greg, reconnected with an old flame after his divorce, and soon enough, they started dating again. However, the impact of toxicity from his marriage ran so deep that he never could let his guard down and be 100% present in the connection.

At 50, his girlfriend, Linda, had little patience for mind games and putting up with dating a divorced man red flags, so she called it quits. Uncle Greg is still licking his wounds. Talking about how it’s not uncommon at all when people start dating at an older age, clinical psychologist Dr. Carla Manly says, “Unresolved emotional issues can affect the way someone relates to you. It’s crucial to understand how this baggage influences their ability to form healthy attachments.”

3. Power imbalance

An age gap can result in skewed power dynamics where the older man holds more influence, whether emotionally, financially, or socially. This can mean,

• Setting rules about who you can or cannot meet
• Not respecting your privacy
• Not compromising
• Disregarding your interests and desires
• Shaming you

All of these behaviors can leave you feeling uncomfortable standing up for yourself and leave you at risk of being manipulated. You see how ignoring red flags can be detrimental not only to the health of the bond you’re trying to establish but also to your mental health and emotional well-being.

4. Lack of flexibility

One of the red flags on a date with an older man to keep an eye out for is his lack of openness to try new things because it suggests a propensity for rigidity. Psychotherapist Esther Perel says, “A partner’s rigidity can stifle personal growth in a relationship. Flexibility is essential for navigating the evolving dynamics of any partnership.” Older people can be set in their ways, resistant to change, or unwilling to adapt to new ideas. However, when embarking on a new journey with a potential partner, one has to make room for adjustments and compromises.

If the older man you’re dating is unwilling to do that, it can not only be frustrating but also impede the growth of the relationship. There are only so many times you can ignore his refusal to try new things, budge from his schedule, or agree to do something just because you want to before it turns into a sore point in the relationship.

5. Misaligned life goals

This can be one of the unpleasant consequences of dating an older man that is no one’s fault really. Simply because you’re in two different places in life, there is a high probability of misalignment in life goals such as,

• Career aspirations
• Family planning
• Financial choices
• Spiritual outlooks

“Being at different life stages means you may want fundamentally different things, and those differences can widen as time goes on,” says Dr. Terri Orbuch, marriage therapist. If a couple fails to find common ground over these areas of misalignment, it can create conflict over time. The best approach would be to have an open conversation about these subjects when you begin dating an older man so that there is clarity about how far you can make it as a couple. 

Related Reading: 15 Examples Of SMART Goals For Relationships And How To Set Them

6. Unwillingness to commit

If you’re looking for a long-term partner to build a life with, a reluctance to commit can be one of the most glaring red flags in a relationship with a man who is older than you. This is a real possibility because older men, having been there and done that, can be wary of committing and emotionally investing in a new partner and may prefer to keep things casual. Psychologist Dr. Samantha Rodman says, “Commitment is about shared vision and goals. If someone has been burned before, they may approach new relationships with hesitation or even avoid commitment altogether.”

7. Age-related insecurities

Picture this: It’s Saturday night, and you want to go out and have fun, but the person you’re dating is not on board with the idea because he wants to “turn in early” or “night clubs are too noisy” and he’d much rather stay in and catch up on some reading. You make plans with friends, go out, have a blast, and splash it on your stories.

Your man sees them the next morning and is green with jealousy and throwing a hissy fit because you’re hugging a guy friend in one of the photos. What a dampener, right? But not uncommon age-gap relationships. An older man may be insecure about your interactions with younger men, especially your peers. This can lead to jealousy and controlling behavior.

8. Financial control

An older man’s financial stability can be part of his appeal since it translates into greater confidence, ease of living, and a taste for finer things in life. However, it can be a double-edged sword if he starts using his financial resources as a form of control, subtly or overtly. Trying to use money to have his demands or expectations met is one of the red flags when dating an older man you need to be watchful of. This can look like,

• Love bombing you with grand gestures
• Buying expensive gifts to get you to agree to do something you may not want to
• Offering financial support to curtail your freedom. For instance, giving you a car but then controlling where you can go

Psychologist Dr. Susan Krauss Whitbourne explains, “Money can become a tool for control in relationships, especially when there’s a significant financial imbalance. This can lead to dependency and power struggles.”

Related Reading: 15 Examples Of Manipulation In Relationships

9. Cultural or generational gaps

When the age gap is so wide that you and the man you’re dating belong to different generations, finding common ground to connect over can prove to be a challenge, creating a disconnect. This gap can also manifest in differing

• Values
• Communication styles
• Expectations about gender roles
• Perspective on relationships

“Cultural and generational differences are often overlooked, but they can deeply influence how partners connect and understand each other,” says Dr. Gary Chapman, relationship expert and author of The Five Love Languages.

10. Fear of aging alone

Some older men may rush into relationships out of fear of aging alone. The consequences of dating an older man in such a situation can include,

• Emotional burnout
• Loss of personal space
• Misaligned relationship goals
• Pressure to fill a void

“The fear of loneliness can drive individuals to settle into relationships that aren’t necessarily based on compatibility, but on filling a gap,” says relationship expert Dr. Harville Hendrix. Naturally, such relationships can be hard to sustain. Even if you go along with your partner’s escalated relationship timeline, the bond is likely to crash and burn if you constantly feel forced to do things you’re not ready for.

11. Past relationship drama

If his past marriages didn’t work out, you also need to keep an eye out for dating a divorced man red flags, which can be as diverse as they come. Some of the possibilities include:

• Lingering resentment
• Unhealthy boundaries with ex
• Ongoing legal, financial, or custody battles
• Commitment issues

“Untangling from past relationships can take time. If someone isn’t fully free emotionally or financially, this baggage can negatively influence new relationships,” says clinical psychologist Dr. Judith Sills. Before you give into the temptation of dating an older man you have the hots for, see to it that there is no drama involving ex-partners, children, or financial obligations because it will invariably impact your dating life.

12. Fear of rejection

Another one of the common red flags in a relationship with a man who is older than you is his constant fear of being rejected, dumped, or abandoned because a part of him cannot shake off the feeling that you’re too good for him. He may fear that his age makes him less desirable to you, leading to:

• Insecurities
• Jealousy
• Attempts to overcompensate

13. Parenting conflicts

If the man you’re with is also a single parent, then there can also be red flags when dating a man with a child to contend with. For instance,

• The dynamics of his co-parenting relationship with his ex can influence your relationship
• Parenting responsibilities may get in the way of your dating life
• There may be conflicts about your involvement in his child’s life

Tips For Dealing With Red Flags When Dating An Older Man

These red flags when dating an older man while concerning, don’t have to mean the end of the road for you and your partner. Provided he, too, acknowledges the underlying issues and is willing to work on them, you can find a way to date successfully and go on to build a fulfilling relationship.

Relationship counselor Dr. Stan Tatkin says, “It’s essential to recognize when differences in age and life stages create incompatible dynamics. While age-gap relationships can work, they require strong communication and mutual respect to bridge these gaps.” With that in mind, let’s look at these 7 easy-to-implement tips on dealing with red flags when dating an older man:

Related Reading: How To Improve Your Relationship: A Therapist Advises

1. Open communication

Ignoring red flags like control issues, emotional baggage, or power imbalances isn’t going to make them magically disappear. So, focus on addressing them early through open and honest conversations. Be upfront about how his behavior makes you feel and establish healthy boundaries. Emphasizing the importance of open communication, clinical psychologist Dr. Sue Johnson says, “Effective communication is the foundation of any healthy relationship. Don’t wait until resentment builds—discuss issues as they arise.”

2. Set clear boundaries

Psychologist Dr. Henry Cloud says, “Setting boundaries shows that you value yourself and your personal space. It is vital to ensure mutual respect in the relationship.” Setting clear boundaries can be especially effective if you’re dealing with power imbalance or control issues when dating an older man. Through boundary-setting, you can make it clear that you value independence and equality in decision-making, whether it’s financial decisions or daily activities.

3. Assess compatibility

Before you get too emotionally invested, it is important to assess your long-term compatibility given that you and your partner are in different life stages. Discuss your future plans and expectations to determine if you’re on the same page regarding major decisions like career, family, or lifestyle.

Marriage and family therapist Dr. Terri Orbuch says, “Being at different life stages doesn’t mean you’re doomed, but it does require careful discussion about what both of you want and how those desires can evolve.” If you can’t find common ground, it’s best to keep things casual and enjoy each other’s companionship while it lasts and not get too emotionally involved.

4. Nudge your partner out of his cocoon

If your partner is rigid or set in his ways, nudging him out of his cocoon can foster personal growth and adaptability in the relationship. You can do this by,

• Introducing new activities
• Shared hobbies
• Exploring new perspectives together

Psychotherapist Esther Perel says, “Relationships thrive on curiosity and willingness to grow together. Encouraging personal development can breathe new life into an otherwise stagnant relationship.”

Related Reading: How To Balance Independence In A Relationship?

5. Foster independence

Relationship expert Dr. Margaret Paul says, “Maintaining independence in a relationship is crucial for your well-being. It fosters balance, keeps you grounded, and prevents codependency.” Don’t let the excitement of a new relationship overshadow your life. It’s a slippery slope to giving control of your life to your partner. Ensure that you maintain your independence—financially, socially, and emotionally. Having a strong support system and personal interests outside the relationship helps.

6. Address the elephant of emotional baggage

Dealing with emotional baggage is par for the course when dating older men. The extent may vary but it exists. To make sure that this baggage doesn’t loom large over your romantic life, it’s important to address it head-on. One handling a partner with emotional baggage, clinical psychologist Dr. Carla Manly advises, “Unresolved issues from past relationships can become toxic in a new one. Encourage healing, whether through counseling or introspection.”

7. Seek professional guidance

If the red flags persist or you feel overwhelmed, consider seeking relationship counseling to help you and your partner navigate these challenges. A neutral third party can offer insight and guidance that is sometimes difficult to find within the relationship itself. If you’re looking for help, skilled and experienced counselors on Bonobology’s panel are here for you.

Final Thoughts

While red flags can be concerning, they aren’t always deal-breakers. Addressing them with maturity, patience, and honest communication can help resolve underlying issues. However, if the red flags persist, it may be a sign that the relationship is not compatible long-term, and recognizing when to move on is just as important as trying to fix the issues.

Age Difference In Relationships – Does Age Gap Really Matter?

Older Man Younger Woman: 9 Reasons Why Dating With Age Gap Works

Dating An Older Man In Your 20s – 15 Things To Seriously Think About

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