Dating An Older Man

Dating an Older Man: Pros, Cons & Things To Know

by John Santana

Love defeats all geographical and emotional boundaries. No one is ever unlovable. You could be attracted to anyone. Age is just a number for many daters out there. But, is it?

When you are dating an older man, the generation gap fully manifests in your relationship. There will be lots of mending to do for this romance to blossom.

Learn about all things dating an older man, from how to get them aroused to marrying them.

How To Get An Older Man To Fall In Love With You?

1. Show Him Your Ambition

Being as experienced in life as he is, he will not be interested in bimbos with pretty faces only. Unless you want to be a vase with no real skills, you need to make sure you are ambitious to catch his attention.

Successful women tend to be more attractive to older men, especially when you have achieved so much at such a young age. Show him all the things you are capable of. Sometimes, older men despise younger women. They think they are better because of their age. It is important for you to set the tone to establish authority. This keeps the attraction alive.

2. Be Mature

His partying and immature stage is long behind him. You don’t want to start a small fight with him over the littlest things. These fights could be cute when you were young, but not anymore. An older man will find you annoying if you keep bringing up fights.

At this point in their life, they long for peace. A loving relationship is all they need. If you do encounter relationship problems, sitting down and talking about them is the best way. They do not appreciate unnecessary drama, nor do they feel this is the right way to show love.

3. Do Your Own Thing

Once he is passed that age where he wants to be lovey-dovey all the time, he values privacy and space. He likes spending time with you nonetheless but he no longer seeks constant physical companionship.

He is happy to be doing his thing and get together whenever possible. It should be the same for you. Being clingy will drive your man away. You should be investing more time in yourself and showing him your independence.

What Should You Expect From Dating An Older Man?

Couple Holding Hands While Reading Books

1. He Is Here To Give Logical Advice

When you feel emotional, you may find your partner to be overly calm. It doesn’t mean he doesn’t care. He shows his love differently. Being the practical one, he wants to solve your problems by giving logical advice.

Don’t be frustrated if it sounds like he is being a boss instead of a lover. He wants to tackle the root problem by giving a helping hand. With him, nothing will feel too difficult to deal with. But you may feel a bit sad when he is not there to give you a shoulder to cry on.

2. There May Be Kids Involved

It is quite likely that his ex-wife or children will be in the picture. You need to think about how likely you will accept it. If you are strict on the “ex is off-limit” policy, this may be the wrong relationship to pursue. He will never cut ties with his previous family and it is not right to ask him to do so.

They could be genuinely good friends or maintain good communication for the sake of their children. Either way, they will interact frequently. There will be times when they attend school events for the kids. It is none of your business and you can’t intervene. You may feel left out but that is part of the package when you date a divorced older man with children.

3. You Will Be Trying Lots Of New Things Together

Since you were born into a different era, your mutual language could be different. You may be too slangy for him to understand. Your favorite leisure activities sound so foreign to him. It takes time to get to know each other.

The end result will be rewarding. You learn so much from someone older while he learns about trending activities. Both of you will be trying lots of new things together. Some of these things can be hard to accept for either one of you due to the age difference. This is when you show respect by supporting his beliefs. Likewise, he will try his best to understand your point of view.

4. This Relationship Will Either Go Too Fast Or Too Slow

It is hard to depict the speed of the relationship as it comes down to his preference entirely. Some older men will jump into moving in together after a few dates because they have wasted time in the past. Others will take their sweet time to observe.

It is easy to separate these two groups of older men. As soon as you go on your first date, it becomes clear which group they belong to. They can either be overly excited about doing couple activities together or too cold to even suggest establishing a relationship. Rarely will an older man goes in between.

How Do You Know If An Older Man Is Interested In You?

1. He Asks About Different Aspects Of Your Life

An older man does not express his love the traditional way. He is not going to stare at you and exclaim at your beauty. Rather, he wants to know everything about you. His questions about your childhood and your parents are signs of love.

Not a lot of men care about other things in your life but an older man will take an interest in things you never knew mattered. You would be astonished by his knowledge of you. He cares and remembers every little detail by heart.

2. He Listens To Your Past Without Giving Judgment

It is easy for an older man to be critical. With his life experience, he could have a lot to say about you. But when he is in love, he retains the judgment of himself because he understands the most about the repercussions of judgment.

At his age, he has probably lost relationships due to it so he knows when to keep his mouth shut. The entire relationship feels refreshing because you can be true to yourself and get accepted. He will not try to change you because that is what love should be.

3. He Buys You Things

He is not trying to be a sugar daddy but he is likely earning significantly more. Therefore, he is willing to shower you with gifts. For him, this is in no way saying he is buying you. This is how he expresses love.

He wants to be the provider of this relationship. With different purchasing powers, he wants to step up so you don’t have to worry about not getting the material life you deserve. It can be confusing at times as you may feel he is treating you like a sugar baby. He means well and is not demeaning.

Our Favorite Online Dating Sites To Date An Older Man

  • Adult FriendFinder – casual and open minded, you can find plenty of sexy older men here
  • Ashley Madison – filled with loving but married older men, this place is packed with mature men looking for love and excitement that they have lost in their relationships

What If The Older Man Can’t Satisfy You Sexually?

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Being unable to perform sexually is a big problem for many older men. As they age, their sex drive seems to proportionally drop. Even if they desire sex, they are no longer able to perform as they could in their prime days.

Regardless of age, being unable to satisfy your other half sexually is humiliating. Therefore, knowing how your partner’s age limits him, you should not be vocally dissing him. There are plenty of ways to get him into the mood. It may take longer than your previous partners but that has to be done for an older man to be aroused.

Try different tricks and see if a particular one works for you. Don’t hesitate to introduce toys in bed. Sometimes, an older man may prefer to use toys to give his partner an orgasm. That way, he does not have to worry about his physical shape while being happy about satisfying you. It is a win-win situation.

On the other hand, if his struggle seems to suggest a problem deeper than age, you should encourage your partner to seek medical advice. Older men may have other underlying health issues that prevent them from getting aroused or performing in bed.

Attend couple’s therapy if necessary. It is a great way to drop the mental stress and discuss how you can maintain a healthy sex life. Due to the different expectations, couples with a huge age gap may find it challenging to confront each other. With the help of a therapist, you can take a better look at your own circumstance and how to solve the issue.

How To Communicate With An Older Man?

Dealing with an older man is different from dealing with a teenager. He does understand all the little hints you drop but it is unlikely that he will respond. For the most part, he believes hints are a stupid way to express your needs. If you want something, say it. Playing games with him is not intriguing.

He expects an open discussion where you lay out your thoughts logically. Being irrational or overly emotional will annoy him. He will not hesitate to walk out of a confrontation if you are being emotion-driven.

Unfortunately, your man will not lower his standards because you are much younger. He lives by his rules, which extend to you. Compromising is a big part of the relationship but it is a mutual responsibility. He is not going to cave when you are unreasonable.

Older men can come off as arrogant but they are simply being real. Giving you everything you want may make you feel like a princess but eventually, it will be the bullet that kills the romance. He is here to balance the tone so you both get what you want.

Do Older Men Want To Get Married?

Woman Looking at Her Husband

It really depends on his circumstances.

Some older men came from complicated households with troubled past relationships. They may have been divorced several times with kids. The battle of alimony and a series of failed marriages has led him to believe marriage is just a paper. It does not signify your love, nor does it make romance last forever.

In this case, he can be advertently against getting married. He believes it complicates things. You could be as in love as ever but he knows nothing lasts forever. This relationship could fall into pieces. Facing another divorce is not on his to-do list. You are unlikely to change his mind because of his personal experience.

His refusal to get married does not mean he loves you less than his exes. Life is a constant lesson, and he has learned his. Staying together without a contractual legal agreement elevates this love for him.

This does not describe all men. For some older men that have been searching for the right one their entire lives, meeting you is like winning the lottery. You are one in a million. He desperately wants to marry you immediately and is not shy to say it. After all the missing chances, he is not going to let this one slip.

How your man will act truly depends on this experience and take on marriage. It is hard to generalize what an older man wants. That said, there is one thing for certain.

It is impossible to change an older man’s mind. He has lived long enough to know pleasing someone by going against their belief is not love. So, if his take on marriage differs from yours, don’t expect to change him because it will never happen.


Dating an older man comes with lots of fun and security. At the same time, you need to grasp their expectations so this relationship will work. Don’t be discouraged by your previous failed relationships.

Hop on Adult FriendFinder and Ashley Madison to find the best dates possible.

John Santana

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