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26 Tips for Women Dating Older Men


Advice for Younger Women Dating Older Men

If you're dating - or thinking of dating - an older man, you may be concerned about keeping his interest because relationships, issues in relationships and dating have always have been topics with a lot of uncertainty. Anyone who’s been in a serious long-term relationship knows the journey isn’t without certain challenges and adding a significant age gap into the tricky situations usually heighten the challenges. However, while your concerns for enduring relationship are perfectly natural, keeping his interest is not as problematic as you might imagine. When you are dating a young man, there are always things you have to think about- how to do your hair to suit modern trend, putting on fashionable dress, how to surprise him on some special occasion, etc. But, when that man is a lot older than you, the expectation will be different to some extent. When it comes to dating a man who is older and who already has the clear image of what he wants from life, there are some new challenges that you might encounter; new moments that might come up you didn’t take into consideration and you now have to deal with. Here are some tips for dating an older man you will surely need:

Be understanding

The first thing you need to understand when dating an older man is that there will always be a difference in what both of you expect from each other. Since there is generational gap, it might happen that he is expecting a lot more mature behavior from you, as you are expecting he will always have the time to go out and have fun with you or hang out in a club up to 5 am. Neither of those is wrong, but be understanding of his lifestyle and try to meet him half way. Don’t get mad at him when he doesn’t give you attention you want. One of the biggest allures for younger women dating older men is the fact that older men tend to be more established. While you initially marvel over his fanciful home and progressive career, if you want to make the relationship work, you have to understand that he must work hard to pay the bills and continue climbing the corporate and societal ladders. Sometimes, this means less attention for you and almost always means that you and your man cannot be together every waking moment. Don’t be disappointed if he can’t stay up chatting with you until late every night. Instead, work out a schedule to ensure that you both are able to spend time with one another without compromising your individual responsibilities. You have to understand that different mindset comes with ages and that it takes time for both of you to get accustomed to one another and the way you see things. Just be patient and don’t let new situations defeat you.

Think less of the age gap

When you meet an older man that you want to date, don't let age be a barrier because relationship is usually based on compatible personalities, common interests, and chemistry. Age difference between two people who really like each other is a non-issue because if you both have agreed to begin dating, you have moved past whatever age gap you may have. Treat the relationship the same as you would with a guy your own age. Accept the fact that there is a generation gap but don’t run the risk of making your man feel older than he actually is. Play it cool and think less of the age gap. Some men are just as sensitive about this aging as women so don’t joke around about his first gray hair.

Don’t be a trophy girlfriend

Some men chase younger women as a way of making themselves feel younger or to stroke their own ego. Older men just like their younger counterpart also use women as sex objects. Protect your heart and self-worth by not jumping into bed or accepting expensive gifts too quickly. If your older boyfriend has a nice house and steady income, you might be eager to move in with him. Don't rush things. There's nothing wrong with taking things slow. Otherwise you may wake up one day and realize that you are living in an expensive house, driving a flashy car and using a credit card that is in his name, just for sex. The realization that you have essentially become a prostitute will diminish your self-worth. You have more to offer than a hot body.

Don’t assume he’s going to use you

However, it is wrong for you to assume that the older man is just in for "hit and run" relationship. Yes, there are older men who want to date you simply because you're young and attractive, but that doesn't mean all older men are just looking for a fling. Although some older men treat younger women as trophies, not all of them do. Just as you’d do with a younger man, choose wisely. Pay attention to the way he treats you and the language he uses. This will tell you a great deal about his intentions and you can then make your decision.

Don't become dependent

While men do appreciate a woman who needs them, they also respect a confident woman who is independent. A woman who is able to make decisions, earns money, and takes care of herself. When you become dependent, you place a burden on the relationship. Even if a man earns much more than you and can easily take care of all your expenses, he will feel stifled and will likely loss respect for you if he has to pay all your bills. So stay self-assured, confident, and fairly independent.

Always be yourself

Despite your age difference, you both have accepted one another for who you are. Don’t change who you are only because you are dating someone a lot older and more mature than you. Just because a man is older and has more experience doesn’t mean he knows everything. You have life experiences and knowledge of your own that has value. Don’t be afraid to express your opinions or offer your advice. Keep being yourself and always keep an open line of communication between one another. Remaining true to who you are is important.

Don’t live isolated life

Just because you are dating an older guy, doesn’t mean that you will have to leave all your friends behind and never see them again, start hanging out with his friends or to behave like you’re years older all of a sudden. Find the time for everything and balance your social life. Go out with your girlfriends and do the regular shopping as you usually do, while your darling is at work. You might want to turn down every invitation to hang out with him and his friends, since they're all so much older. No, don’t do that. You should also be careful not to live isolated life, and try to meet with his friends and coworkers when he takes you to some business dinners or cocktail parties. If he's the right guy for you, then he'll find a way to make you comfortable. Don't feel like his friends are judging you, because they're probably jealous that he landed such a beautiful, young woman. Learn a variety of topics that might interest a professional man or one involved in business or current events. While you don't have to be an expert on the things that interest a man with an established career, you need to know enough to discuss intelligently. It's only when you're completely clueless and naive that he might feel uncomfortable talking to you about social issues or inviting you to meet with his friends at cocktail parties.

Make sure he’s not the jealous type

It is a known fact that older men are not going to be as insecure as younger men. They understand that you have a life of your own to live, just as they do. However, if he is prone to jealousy or possessiveness, this will be a problem because there are going to be times when you want to go out with your friends without him. He should be able to understand that being unnecessarily possessive leads to all sorts of trouble and that spending time apart sometimes is important. If he is unable to accept this, move on to a more confident man.

Show off your skills in the kitchen

It is not really compulsory that a woman needs to know how to cook and do domestic chores in order to entice any man, but it’s certainly an attractive trait when men are looking for the woman they want to marry and raise their future families. All the knowledge doesn’t come instantly. You have to learn how to cook and make mistakes as you learn how to cook. So, show off your skills in the kitchen. Your older man is sure to appreciate it.

Learning from each other

The good thing about being in a relationship with a guy who is older than you is that you can always learn new things from him. Since an older man may have a broader perspective on life simply because he is more experienced, you can ask him questions that a younger man might have no clue. He will be more than glad to be the one you come to when you want to learn something new. You can learn about career growth or money management because he is likely to be very supportive, offering you advice from his experience, referring you to professional colleagues, or simply pointing out where you can find your best answers. With a larger age gap comes completely different life experiences. You can equally teach him new and interesting things. When you make a reference he doesn't understand, don't awkwardly move past it. Show him the TV show or movies you were talking about, because he might end up loving it. You’ve heard the saying, “with age comes wisdom”. Use this to your advantage: learn from him. The next time he tells you that you're doing something wrong with your career or friends; hear him out instead of immediately getting mad. He has more experience in life and you should use that and not get angry at him for pointing out something you don’t like.

Don’t try to be his kids’ mom

If the man has kids from past relationship/s, don’t try to be their mom. They already have their mom/s. Think of how you would feel if the shoe were on the other foot. You wouldn’t want a younger woman (complete stranger) trying to take your place in your children’s lives.

Ensure you’re on the same page

When dealing with a man your age, discussing children and marriage with him may need sometime. But if your boyfriend is much older, those things could be on his mind. Discuss his stance on commitment and children. He may be ready to settle down and start a family, while you are just getting started as an adult and have no interest in settling down. You should discuss when you will be ready to settle down so the two of you are on the same page on plans about your future. Or, he may be at the stage in his life where he has already been married, has kids and has no interest in ever getting married again. You need to know to enable you take a decision about your own future.

Be ready for his baggage

One thing that comes with adding more years to your life is baggage. Everyone has it, but some people have more than others. If you're going to date an older man, you have to understand that he has more baggage than you do, because he's so much older. Know what you are getting yourself into before you get in too deep. If you want to be with him, you can't blame him for having baggage like an ex-wife or child. You need to be able to accept his past if you want the relationship to work.

Don’t allow him run your life

His age doesn't mean that he has to run your life for you. He shouldn't always be the one deciding what you'll wear, eat and the destination of your vacation all the time. Relationships should be about equality. He doesn't get the upper hand just because he's a bit older.

Support him

When you are a younger woman dating an older man, you have to accept that he will sometimes have problems you won’t be able to understand quite yet, because you’re at two different stages in life. Whether it’s a career change or a midlife crisis, the best thing you can do is to always remain supportive.

Be spontaneous

Every now and then, stray away from the norm and add an element of spontaneity. While this applies in any relationship, it is especially important when dating an older man. Do something nice for him and surprise him with something cute once in a while. It could be something simple like trying a new restaurant for your weekend date, or a romantic dinner with candle lights or a nice warm bath for him to relax after a hard day’s job. This will make his day refreshed, no matter how many meetings he had at work. Tell him about something new you learned or some new store you saw with the things he likes. He might not always be up for every suggestion you have about doing new and spontaneous things that get him out of the everyday life, but that doesn’t mean you should stop suggesting. He’ll be surprised with how much passion you can provide him with and that will keep him more alive than ever and will appreciate them.

Be respectful to his ex

She is not your enemy or your competitor. Not only will she be less likely to make your lives less of a living hell, but she’s the best resource for learning who this man is because she has known him for a long time. In addition, if he was ever abusive or unkind to her, you need to know. Of course some women are bitter and may not be the best judge of your new man’s character.

Don’t assume he’s wealthy or successful

If you are drawn to older men for the security they bring, it will be disastrous to easy show it. You will be classified a “gold-digger”. It is equally wrong to judge him by his expensive suits, watch and nice car. He may have had a wealthy ex-wife or he may be paying a huge chunk of his salary to his ex-wife as alimony or his kids’ upkeep. Either way, this doesn’t provide any security for you.

Be careful how to handle his friends’ wives

Do not call his friends’ wives ma’am, do not flirt with their husbands and don’t dress too sexy, thereby giving them the impression you are a whore, especially in the beginning. When he takes you out, he wants to know how you will fit into his world. That includes his friends and their wives.

Pursue your interests and don’t sacrifice your own goals

When you do your thing, such as pursue your favorite athletic interests, forms of entertainment, education, or career path, you will give your older man space to do his thing too. Some men, especially men at the height of their career, often need space to just figure out their next move in life or how to resolve work-related problems. You should not allow his plans to interfere with your accomplishing your own goals. If you're busy doing your thing, then you won't smother him with an excessive amount of attention.

Don’t allow your friends make jokes about him

Your friends will have fun joking around about dating “the old guy”, but do your best to nip this behavior in the bud. If you joke around behind his back, they will think you don’t care if they do it to his face. It’s disrespectful and it won’t help your relationship. Think of how you feel when you hear your lover’s friends say things about you that are disrespectful.

Disapproval of your family and friends

There is also the fact that your parents, your friends and other family members aren't going to approve of you dating an older man, but if you have the patience and wait for a while, you’ll see that they will relax and get to see that you are happy with him. If it's clear that they're never going to approve, then you have to learn to not let their opinions bother you.

Keep an open line of communication

If you get into a long-term relationship with an older man, you will need to keep an open line of communication because as you are finding your place in the world your goals at the beginning of the relationship may change. Some of the changes will be, in part, due to the knowledge and experience he has shared with you. It’s extremely important to communicate your needs, desires and goals every step of the way, especially if they affect him and your relationship.

Allow some time

This is one of the best tips on dating an older man, because the relationship with a man who is already matured and pretty much settled is a lot different than the one with a man who is more your age and still indecisive. Mutual respect and affection is gained over the time and there will be a lot to learn from every new situation you come across with him.

Don’t be intimidated

Don't feel like you don't measure up. You just have to be confident. You might not have a stable job or be the best kisser, but it's because you're still young and with time you will gain experience and become better as you have time to learn new things, and he can be the one to teach you. However, every day you are rapidly growing and changing.

Know when to say goodbye

If you have no desire to have anything but a fling with this man, know when it’s time to say goodbye. It is not in your best interest to stay in a relationship that could jeopardize the possibility of involving in a more serious one for too long. If you want kids, you don’t want to wait until you’re close to menopause to find someone new.


Saying that age doesn’t matter when you’re dating is ludicrous. Of course it matters because women are susceptible to biological clock. Dating an older man can be a wonderful experience if treated with dignity and mutual respect. There’s no reason a relationship between a younger woman and an older man can’t work out as long both people are happy and enjoy each other’s company and know exactly what they want.


Anthony Modungwo (author) from Benin on November 30, 2016:

sugarbabywebsite thanks for your encouragement and referral.

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