10 Things To Consider Before And When You Date Older Women

Updated August 10, 2023by Regain Editorial Team

When you're dating a special woman, you likely aren't really going to put a big emphasis on how old she is. It's becoming more common for young people to date older women in modern times. This might have been seen as more of an oddity years ago, but it isn't too unusual at all now. Regardless, there are some potential complications that you should look out for if you're going to be dating someone older. Take a look at the following 10 things to consider before and when you date older women.

  1. Your Values Might Be Different

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It stands to reason that your values might wind up being quite different from someone older than you. If you are in your early 20s and you're dating a woman in her early 40s, then that is quite a difference. You grew up during different times, and your perspective will be colored differently due to your upbringing. She was raised in a slightly different time, and she might look at the world differently than you do.

This doesn't mean that two people have to be at odds due to not being from the same age group. You could even have similar values, but there are likely going to be differences in how you think about certain topics. This isn't something that a relationship can't overcome, but not everyone will have an easy time dating someone older. Depending on how things go, you might find it hard to relate to your partner.

  1. Clashing Musical Tastes

One common issue that young people encounter when dating someone older is that they have clashing musical tastes. This isn't always the case, but an older woman might not be into current popular music. If you're dating an older woman and she dislikes your taste in music, that isn't necessarily going to be a dealbreaker. It's just something that you have to get used to. Even younger couples often have clashing musical tastes, and your partner might even be willing to warm up to some of your music over time.

  1. She Might Have Children

It's especially important to consider the fact that your partner might have children of her own. When you date older women, there is an increased likelihood that the woman will have children. Depending on how old the woman you're dating is, she might even have children around the same age as you. This could be a little bit strange for you, and it can certainly make things complicated from a social standpoint.

Dating a woman who has children is different from dating one who is simply by herself. If she has young children, then she is going to have to put them first. Taking care of the kids is crucial, which might take precedence over your relationship in many ways. If your lover has adult children, then you might worry about whether these people will accept you being in their mother's life. It can be a tricky subject and gaining acceptance might take some time.

  1. She Might Not Be Able To Have Your Children

Conversely, you should also factor in her age when it comes to your own desire to have children. If you're a young man and you would like to be a father someday, then it is possible that your partner might not be able to bear your children. If she is already in her 40s, she might be beyond the child-bearing age. Generally speaking, an older woman will have to deal with more potential risks when getting pregnant. This doesn't mean that you shouldn't date her, but it is something that you have to consider.

If you're one of those single men who want to have a long-term, committed relationship with women over 40, then this is a reality that you have to face. It doesn't mean that you can't have children together in some way. Adoption is an option, and some people consider surrogacy. This isn't going to be practical for most people, but it is possible. 

  1. People Might Mistake You For Her Son

Another awkward thing to consider is that people might not assume that you're a couple when you're going out somewhere. When you're walking around a store or somewhere else with a person your own age, they might look at you and think you're in a relationship with this person. This isn't likely going to be the case when you go out with an older woman. You might have to deal with some awkward moments of having people call you her son or nephew.

This could even wind up leading to your lover feeling self-conscious about going out with you. She might feel like she is too old for you and that people look down on her for dating a younger man. Some people hold views like that, but it is up to you to decide whether this relationship is worth pursuing. If you really do love the woman, then age doesn't matter so much.

  1. Social Stigma

There is still a bit of a social stigma about younger men dating older women. It isn't as frowned upon today as it would have been a decade or two ago. Even so, there will be people who look down on your relationship, and some might even think that you're an unusual pair. If you want to love an older woman, you have to develop a thick skin and stop caring about what others say about you. What other people think about your love for your partner doesn't really matter at the end of the day. Your love for her is what determines whether or not the relationship is viable and healthy. Just be aware that people will talk and that this can cause your lover some anxiety. You need to be prepared for this so that you can move forward together.

  1. Your Family Might Object

It's also possible that your family might object to this pairing. Your own mother might be a similar age to your new romantic partner. This could cause your family to feel a bit uneasy about your choice. Ultimately, it isn't up to your family to decide whether you're right for one another. You have to understand that not every family will accept you are dating older women. They might take some time to come around, but some of them might find it odd that you're "dating a cougar."

Don't let your family make your decisions for you. If you love an older woman, then that is your choice to make. Just know that some people are going to look at your relationship as strange at first. If your family really loves you, then they will eventually accept your new romantic partner as well. It just might not be a seamless transition at first.

  1. Income Disparity

There is also the potential for an income disparity between the two of you. As a younger individual, you're likely still trying to figure out what you want to do with your life. Most people haven't settled into permanent careers by the time they're in their early 20s. Some people will still be working toward getting a college degree, and others might be working low-paying jobs to make ends meet.

On the flip side, your older girlfriend might already be established in life. She might even be a homeowner with a fairly lucrative career. This isn't always the case, but there could be a big gap between how much money you make and how much money she makes. This doesn't have to hurt your relationship, but it can lead to some confidence issues if you're worried about measuring up to her expectations.

  1. Sexual Differences

There are even sometimes sexual differences that need to be taken into consideration. In modern times, people have become very sexually liberated. It isn't unusual for younger people to be more open to different-sex acts and exploring new things in the bedroom. When you date older women, you might find that they will be a bit less open than you might be used to. This isn't always going to be the case, but there could be a gap between what she is comfortable doing and what you're used to doing sexually.

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It's important to make sure that your partner feels comfortable during sex, and you might need to work with your partner to get her to open up over time. She also might not ever be interested in doing certain acts, and you will have to accept that. Sex is an important part of a healthy relationship, so try to talk about it and move forward in a comfortable way for both of you.

  1. Expectations

Even expectations can be different when you're dating an older person. This can actually go several different ways. For example, your significant other might not be interested in marrying again if she has already gone through a messy divorce. Her life experience might make her want to shy away from certain things, so you might wind up feeling like you aren't being given a chance if you really want to get married someday. It's also possible that the older woman might be more serious than you would like if you were looking for a casual fling.

It's important to make sure that your expectations match up properly. You don't want to hurt your new lover, and you also don't want her to hurt you. If you have open and honest communication, then you can avoid many complications. Do your best to determine what you both want out of the relationship before things get too serious. This will allow you to plan, and you'll feel comfortable with where things are going.

Remember That Couples Counseling Can Help

Remember that online couples counseling can be a big help to you. If you are struggling to get on the same page as a couple, you might need some assistance. Overcoming an age gap is easier when you have dedicated professional therapists on your side. They can work with you to improve your communication skills while addressing any relationship problems that you might be experiencing.

Take the time to speak to an online counselor if you're in need of assistance. They have the right skills to help you overcome even significant relationship issues. It's easy to talk to these counselors, and online counseling is as convenient as can be. You'll be able to reach out whenever it is convenient for you to do so


At the end of the day, if you and your partner are comfortable with each other and the age difference, you can work through challenges such as income, social stigma, family history, and more. If you need additional assistance, relationship counselors at Regain can help

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