How to Have a Relationship with a Much Older Man

Last Updated: December 5, 2022 References

Relationships are hard work to begin with, but it can be even more difficult when there’s a significant age gap between a man and a woman. Not only will you face criticism from outsiders, but there will often be difficult situations within the relationship that will test your love for one another. Luckily, there are many ways to strengthen your relationship with an older man to ensure that it stands the test of time. With a bit of hard work and open communication, an age gap in a relationship can seem non-existent.

Method 1

Method 1 of 3:

Loving Him for Him

1
Focus on personality more than age. An older person can seem full of life and enthusiasm. Likewise, a younger person can be mature and have a lot of meaningful life experiences. Instead of focusing on the number, always focus on the person and how they make you feel.
- If the difference in age does present an issue, make a list to remind yourself of why you fell for this person in the first place.
2
Be on the same wavelength. Being on the same wavelength means that you’re on the same page or that you are both thinking in the same manner. Determine what you both have in common: sense of humor, hobbies, values, goals, etc. and know that none of that can be limited by age.^{[1]
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Expert Source

Alessandra Conti
Celebrity Matchmaker & Dating Coach
Expert Interview. 19 March 2021}
- This is also another chance to connect to your mate through sharing interests or learning new things about one another.
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3
Let go of preconceived notions. Making prejudices and judgments before getting to know a person can be dangerous because it tends to lead to negative thoughts that can change behaviors towards others.^{[2]
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- The first step is to acknowledge that you have prejudices. For example, maybe you think that older men only seek younger women to make them “trophy wives.”^{[3]
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- After you recognize your preconceived notions, challenge the irrationality of them by examining how untrue they are. Seek out examples that disprove your prejudices.
4
Treat him as you would any other boyfriend. If age is nothing but a number then you should have no problem treating your mate with the same love and respect as previous (younger) boyfriends. Don’t put him on a pedestal and don’t think that he should be “more than” any of your other boyfriends: more mature, more established, more financially stable. Get to know him before passing judgment on whether or not he deserves your love and affection.
- If you find yourself expecting more from him, remind yourself that those are your prejudices creeping in. Challenge them by telling yourself that he is just like any other man.

Method 2

Method 2 of 3:

Prepare for Difficulties

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Prepare for awkward questions. Many outsiders will find your relationship interesting and weird and will ask all kinds of annoying questions because of it. Be prepared to face questions that are loaded with prejudices and assumptions about what type of people you are. Prepare stock responses to the most common questions, and learn how to ignore the negative responses that you’re bound to receive.
- For example, many will ask how you met and assume that you were seeking an older wealthy man or he was seeking a younger trophy wife. Try to prepare responses to questions like this. For example, you can respond by saying, “What’s in his heart is more important than what’s in his wallet” or “I love the fact that he matches my confidence and my stability like no other man has been able to.”^{[4]
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- You can always respond to negativity by being patient, calm, and trying to explain your perspective to those who will listen.^{[5]
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- You can also grow thick skin and learn to respond to negative responses by ignoring them and showering more love on your relationship.
2
Avoid being a trophy. While it is a stereotype, it is also true that some older men only seek younger women for their looks. Not only does it stroke their ego, but it also makes them feel younger. Avoid jumping into a sexual relationship too soon so you can focus on building a solid foundation for a relationship.
- Be clear about your intentions. If you are seeking a long-term relationship be clear about that from the beginning. If he realizes that you are looking for more than he’s willing to give, he may stop pursuing you and save you some time and energy.
- Be honest about the status of your relationship. Living in a condo in his name, driving a car he’s paid for, and going on shopping sprees with his credit card all sound great, but if he’s only coming by for sex, then the dynamic of your relationship needs to be reevaluated.
3
Accept his baggage. The longer you live the more experiences and baggage you accumulate. For older men, it could mean more sexual partners, an ex-wife (or two), and children who are close to your age. You have to be prepared to accept his past, and to also face with it occasionally.
- The first step is to determine if it is something you are willing to accept. If you said you never wanted children and he has a gaggle of them, you’ll have to reconsider your priorities.
- Realize that baggage can also be seen in a positive light. Think of it as a past, a commitment, or a lesson learned that has helped him grow into a better person.^{[6]
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4
Realize that your friends are different. When there is a significant age difference in relationships, there are also typically age differences among groups of friends. That often makes it difficult to do group activities because it tends to lead to bored partners or awkward exchanges among friends.^{[7]
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Research source} Realize that it is okay to not include your mate in all your plans and vice versa. Otherwise, be prepared for uncomfortable interactions each time.
- Pick and choose your events. For example, instead of inviting your mate to a double keg house party, try inviting him to a night of bar hopping instead.
- You can also learn to compromise or meet in the middle.
- Don’t avoid hanging out with your friends just because your mate doesn’t fit in. There are always ways to divide your time among them.
5
Prepare for late-life changes. If you’re in the relationship for the long-haul, thinking about life in the future is necessary because you and your spouse will be at different stages in your life. Consider late-life changes such as retirement, caregiving, failing health, and drops in sexual drive. Prepare for these inevitable changes by having open and honest discussions with your mate.
- Before having a conversation with your mate, be honest with yourself and determine whether or not you are willing to stick with your mate through all of these changes. If you cannot see yourself accepting these lifestyle adjustments, then you may want to reconsider your relationship.

Method 3

Method 3 of 3:

Being More Mature

1
Be understanding. There will always be differences between you and your mate and these can usually be more extreme than in typical relationships. There will be differences in lifestyle, career, behaviors, and friends. The best thing you can do is understand these differences instead of getting emotional. Learn how to meet him halfway and understand when things don’t go your way.^{[8]
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- When you find yourself getting emotional, put yourself in his shoes. Being able to feel empathy will limit your need to be right and will instead strengthen your love.^{[9]
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- For example, imagine you want to go out to a rock concert on a Tuesday night but he opts out due to work. Understand that he has different priorities and that he doesn’t love you any less because of his response.^{[10]
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2
Support him. In every relationship there will come a time when your mate will be down and out and your job will be to support him. Even though he may be facing problems that you may not understand, you should still be there to show him that when he breaks down, you will always be there to lift him up.^{[11]
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- Sometimes just being there to listen is a big help. Give him time and space to speak and listen without judgment.
- Avoid false or empty reassurance such as “everything is going to be okay.” Instead, offer genuine words of encouragement only if he is willing to hear them.^{[12]
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3
Inspire him. Sometimes older men tend to settle into a certain lifestyle to the point that it becomes boring and routine. Try to inspire him to do more and to be more. Usually it is the older man who motivates the younger female to achieve her dreams, but break that stereotype by encouraging him to do more with his life.
- For example, encourage him to take the guitar lessons he always wanted or tell him about a new venture you’re taking on. ^{[13]
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4
Embrace differences. Instead of allowing differences to create conflict in your relationship, realize that differences can be a learning opportunity. With age comes completely different life experiences. Embrace them by teaching each other new and interesting things.^{[14]
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Expert Source

Alessandra Conti
Celebrity Matchmaker & Dating Coach
Expert Interview. 19 March 2021}
- When disagreements do arise, remind yourself to walk in his shoes. Just as you would respect a foreigner’s culture, you should also learn to respect your mate’s opinions and experiences.
5
Be patient. Learning to be good-natured and tolerant are great skills to learn. Your relationship will always present difficulties: whether it’s his busy work schedule or your frustration with new situations. Instead of getting overly emotional and throwing in the towel, be patient and attempt to work through problems.^{[15]
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- Learn to sit in your discomfort. Sometimes you will be angry, sad, or upset but instead of acting on your emotions, remember that your feelings are uncomfortable, not intolerable.^{[16]
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- When you recognize your feelings, learn to talk yourself out of them. Say things like, “I don’t like this feeling but I can manage it” or “This is what happens to me when I’m bothered, but I can handle it.”
- Once the initial emotion passes you can effectively communicate concerns with your mate.

Expert Q&A

Question

How much of an age gap is OK?

Alessandra Conti
Celebrity Matchmaker & Dating Coach
Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).

Alessandra Conti

Celebrity Matchmaker & Dating Coach

Expert Answer

It depends on how old you are. Teenagers really shouldn't be dating anyone who isn't a teenager; however, if you're under 21, a 2-3 year age gap should be safe. Ultimately, the older you get, the less age gap matters. At a certain point, it becomes a free-for-all.
Question

What are red flags when dating an older man?

Alessandra Conti
Celebrity Matchmaker & Dating Coach
Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).

Alessandra Conti

Celebrity Matchmaker & Dating Coach

Expert Answer

A big red flag is when you both have different life priorities, like marriage and children. If you aren't on the same page there, you should take a step back and decide if this is a relationship that you want to invest your time into.
Question

What are the advantages of dating an older man?

Alessandra Conti
Celebrity Matchmaker & Dating Coach
Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).

Alessandra Conti

Celebrity Matchmaker & Dating Coach

Expert Answer

Dating an older man can be really fun and interesting! If you both grew up in completely different eras, it could be really fun to learn about his cultural experience growing up. If you both grew up in the same era, you could still view your relationship as an exciting adventure, especially if you have different perspectives.

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Warnings

Never lose sight of who you are. Always remember that the only person that can satisfy all of your emotional needs is yourself.

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Never date an older man if you are under 18--it can get both of you in major legal trouble.

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Just like you can make him feel young, you can also make him feel old. You have to find the balance.

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Sometimes, older men see younger women as more of a daughter. Avoid misreading these feelings for love.

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Some older men seek out younger girlfriends because they think women over 21 are physically unattractive. Despite his objections, you're going to get a little older every day. Be sure that he's with you for you, and not your youth!

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