The DOs And DON’Ts When Dating An Older Man

Last Updated on January 18, 2024 by Lori Pace

You are in love with an amazing man who is 15-20 years older than you. However, you don’t know how to deal with him or what you can expect from a relationship. Let me tell you, dating an older man can have its perks and stability.

However, it is important to realize that things may not always go according to plan even if you feel an intense emotional and physical attraction towards him. Because such unconventional partnerships, like yours, are often influenced greatly by external factors.

2 Major Disadvantages To Dating An Older Man In Your 40s (Or 20s And 30s)

Major Disadvantages To Dating An Older Man

Past Baggage

It is important to understand that he may have a past, especially in the context of relationships. You may have children that are younger than you. You may not be able to see the age difference if he is a handsome, well-mannered man until you meet his children. It can be a harsh reality.


He might be rigid in his beliefs. His personal experiences and opinions would inform his attitudes. He may lack the openness that we had when we were younger. He doesn’t want to change like younger men who are still in the process of their own journey. You are either dating a completed product or a work-in-progress.

Dating an Older Man Rulebook – What You SHOULD Do:

Discuss What Dating Means To You Both

It is important to be clear about your goals and desires when you start a relationship with an older man. Are you open to the possibility of it becoming something more permanent and lasting? Are you open to the possibility of a long-term, committed relationship with your potential partner at this stage in his life?

A candid discussion at the beginning of a relationship can help you avoid heartbreak and a bad breakup. This is a question you should ask your older man if you’re dating. 

Leverage The Benefits Of Dating An Older Man And Learn From Him

A man who is older brings a lot of knowledge to the table, which is one of the greatest benefits of dating an older woman. Keep an open mind and learn from him. You might find yourself pulling the “at your age” card more often than you would like. If not handled with care, it can be a problem. Your older partner will likely be correct about many things, just like anyone who has more experience and years. Instead of trying to outdo him, learn from his mistakes.

Relish Your Youth

You don’t have to be ashamed of having your youth, just because you are dating an older man in your 20s and 30s. Secretly enjoying the fact that your man has his charm and wisdom but you also have the gift of youth is a good thing.

Do not put off the Grand Canyon hike you want to take because your partner isn’t able or willing to go. Your age difference doesn’t have to be a problem when you are dating an older man. You can do that by being true to yourself at this time in your life, without feeling ashamed or embarrassed.

Find Time For Age-Appropriate Activities

People in different age groups, and even generations, may have different ideas about fun and relaxation. He might prefer to read and drink his scotch on Saturday nights. You might want to go clubbing. 

Accept the differences. You don’t have to live with an older man. He doesn’t have to completely change who you are. Make plans with your friends and have fun. It is healthy to pursue your personal interests in relationships. This is especially true for those in age-gap relationships. One of the many benefits of dating an older man is that he will always support your desire to be your own person. You just need to say it.

Brace For Opinions From Family And Friends

Brace For Opinions From Family And Friends

There is a chance that your family and friends will react negatively to you starting a relationship with an older man. There are many negative reactions to breaking the news. These can range from asking questions about the attraction of a younger woman to older men to telling you to stop.

One of the downsides to dating an older man is having to be able to challenge societal norms and other’s ideas about what a romantic partner should look like. But don’t let this get you down. These are the consequences of dating an older guy.

Your family will view their situation as if it were viewed by a judge. How will your family explain this to the community and other members of their family? You may not understand the concept of personal choice. Anything that is radical or outside the norm is unacceptable in society.

Be In Tune With Your Feelings

You must feel connected to your feelings as your relationship develops. Do you feel in love with an older man or are you just falling for him? Are you able to feel a deep emotional connection with him? These questions are essential to help you decide on the future.

After you have found the answer to your questions, it is a good idea for you to ask him how he feels. This will ensure that you are on the same page. Ask the right questions to older men you are dating in order to find the answers you need. Don’t pressure him into committing to something he isn’t ready for. Don’t let him push you to agree to the next step of the relationship.

Accept His Baggage To Understand Dating Older Men Psychology

You might be dating an older man in your 40s who has a 15-year age gap or more. He may have a spouse who has died, children, and maybe even grandchildren. You must be open to the possibility of your partner having children. This will allow you to gain a better understanding of the psychology of ‘dating older men’ and help you to understand your partner’s behavior on certain issues.

Show Affection When Dating An Older Man

Romancing a man older than you may be by years or decades might not be an easy task if he is not your closest friend. It may not be easy at first. You may be wondering, “How do you date older men?” Don’t let dad syndrome stop you from having a great relationship.

Show your affection by touching, talking, and gesturing as often as you can. If he’s comfortable with it, you might try to get into some PDA. You will eventually find your comfort zone together, even if it seems awkward at first. Relax and let no pressure or stress get in your way.

Have Fun

You bring maturity and stability to your relationship if he is older than you. Don’t be afraid to have fun with him. Do not worry about dressing for an older man, or how smart you sound to impress him.

You can let your hair down, have fun, and make him laugh. This will keep your relationship fresh and full of positive vibes. You might be surprised at the joie de vivre he can bring to your relationship if you help him tap into his carefree side.

Initiate Intimacy When Dating An Older Man

Initiate Intimacy When Dating An Older Man

No one is surprised that aging can cause a decline in libido. However, this doesn’t mean your man has to stop having fun in the bedroom. To get your man in the mood, you may need to start to have intimate conversations with him. Do not be afraid to show your wild side.

You can take charge of your bed and try out different sex game for couples such as role-playing. Be prepared to lead and follow, and be ready to be amazed at how well he knows your body.

Treat Him As You Would Any Partner

You don’t have to treat him differently because you are separated by years. Don’t be afraid to show your romantic side, and don’t treat him with reverence. Let go of the fear and accept him as he is.

Dating an older man can be fun and enriching if you have the right mindset and approach. This could change the way you view relationships. Don’t let anyone stop you from pursuing your dreams. These tips for dating an older woman will help you to make the right decision when you are ready to let go.

Dating an Older Man Rulebook – What You SHOULDN’T Do

Push For What He Doesn’t Want

What if you get emotionally involved in the relationship at some point, even though you have agreed to keep it casual? If you want to ask us about tips for dating an older woman, we suggest that you don’t push him into anything he isn’t ready or wants.

Tell him what you feel. The rest is up to him. Before you can set your expectations and goals, it is important to understand the psychology of “dating older men”. Understanding the emotional baggage from his past and his knowledge about his death can have a significant impact on his choices in a relationship.

Lose Your Individuality

It’s wonderful to have someone to guide you and offer wise advice, but you shouldn’t let him take control of your life. It’s important to keep your own identity intact when you’re dating an older man.

You can speak up if you feel strongly about something. Even if it means that you will make the same mistakes he warned against. Without making mistakes and falling, he wouldn’t be as wise as he is today. He learned from his mistakes and was able to move on. You don’t have to miss these important learning opportunities.

Rub His Old Age In

Your partner’s aging years should not be compromised by your youthful joy. It is not a good idea to point out gray hairs or make comments about wrinkles on the hands of your partner. Never use an older man’s age against him. This is one of the most important tips for dating an older woman. It can hurt your relationship, even if you do it in good faith.

Pester Him To Accompany You Everywhere

Doing things together is a key part of a relationship. But, you don’t have to push him to do the things you enjoy. It may not be a good idea to go on a pub crawl until 4 AM. This could not only make him uncomfortable but also cause physical exhaustion. How can you date an older man without coming off as insensitive?

To get to know each other better, find common interests. A Sunday morning spent at the library, or in a bookstore with a coffee or brunch date is a great way to spend it. You can do so many things together, including wine tasting, fishing, and romantic trips to the beach.

Let Your Peers’ Opinions Change Your Mind

Let Your Peers’ Opinions Change Your Mind

Don’t let anyone’s opinion influence your decision if you are certain about your feelings for the man. Parents or friends may not approve, but that doesn’t mean you shouldn’t be able to date an older man with whom you feel a connection. You can make your parents understand why you chose to be with him. You can wait and see if they come around. It doesn’t matter if you see the benefits of being with an older man and are happy with them.

Don’t Assume How He Is Feeling When Dating An Older Man

He may be older than you and have been through the trials of relationships, but that doesn’t mean he will just enjoy the thrill. It is possible for him to develop feelings for you, even if they started casually. Don’t make assumptions about how he feels.

Talk to him if there’s any ambiguity. One of the best tips for dating an older woman is to not let communication obstacles in your relationship slow you down. You can have open and honest conversations about the important things.

Let His Baggage Overwhelm You

Don’t let the baggage of an older man’s life stop you from falling in love. It can be scary to imagine that you might be a stepparent to his children who may not be as old as you. You might be afraid of how his family will react to this relationship.

As long as the arrangement works for you both, it is a good thing. You can trust that the rest will fall into place with a little bit of effort and time. You must both know that his past relationships and family are not yours until you are ready. This will make the most of one of the greatest perceived disadvantages of dating an older man easier to accept.

Try To Make Him Jealous

There’s a chance other men may make passes at you to express their interest or win your favor. It is not a good idea to make your man jealous. This approach will backfire regardless of your motives. Your relationship could end up in shambles. The greatest advantage of dating an older man? He is more likely to be secure in your relationship. Instead of trying to undermine his security, enjoy it.

Be Immature When Dating An Older Man Is A Big No-No

Be Immature When Dating An Older Man Is A Big No-No

It is important to be able to distinguish between being a breath of fresh air from acting like an immature teenager. You should aim to be the former and not fall for the latter. Avoid temper tantrums, unreasonable demands, and doing irresponsible actions that can make your partner feel like you are parenting, not just romancing.

You shouldn’t be able to let him watch you have a ‘knocked-out of your senses’, get you drunk, take you home, or care for you because you want unbridled joy. You should avoid any behavior that makes you want to say “you’re grounded”, as this is immature behavior.

Disregard his Limitations

If you are dating an older man, it is important to recognize that his inability to get things moving between the sheets could be more than just a reduced libido. Older men are more likely to experience back pain, digestive problems, and Achy Joints.

These could be deterrents to intimacy. Do not ignore any health issues he may be experiencing just because you are feeling energized and full of energy. These limitations can seem like disadvantages when you’re dating an older man. There are pros and cons to every relationship. You’ll work out a solution if you are both emotionally invested.

Things You May Be Asking Yourself When Dating An Older Man

How can I tell if an older gentleman loves me?

An older man who loves you will do anything to make you feel special. You will be closer to each other. Once he feels confident, he will not hesitate to share his feelings with you.

Is Dating An Older Man Better?

Dating an older man is possible because of the stability and security he brings to the relationship. He will not play mind games with you or send you hot-and-cold vibes.

What Is An Older Man Looking For In A Partner?

He might be looking for a casual relationship or a committed relationship. It is impossible to predict what kind of relationship you want based solely on your age. It can vary from one person to another.

What Is The Acceptable Age Range For Dating An Older Man?

It’s not unusual to date a man who is 15 years older than you or 20 years younger than you. The old dating age rule states that the maximum age difference acceptable is half his age plus 7 years. If you are 25 years old, your partner should be between the 38 and 40-year age range.

Lori Pace
Lori Pace

Lori Pace is a single mother of three daughters ages 7 and under. As a working mom from home, she balances kids, work and two crazy dogs with humor and love. Follow Lori as she honestly gives tips and advice based on her own experiences as a single mom!