On Dating Much Younger Men (Like Cher). Should You?

It should not come as news that some women “of a certain age” are attracted to men of a certain age — young. Just how young? Ask Cher; her most recent beau, Alexander Edwards, is 40 years her junior.  

Of the age difference and what it means to her? As reported in an article in Vulture, the actress and singer recently tweeted, “LOVE DOESN’T KNOW MATH.”  

The question, however, remains: Will this same equation work for you? To find out, ask yourself the following five questions.  

1. What am I looking for from a relationship with a younger man? 

Before entering into any relationship, asking yourself what you are looking for is critical. As a general rule, if you and your potential partner have different relationship goals, as in you want to travel the world, but he does not, your relationship will likely not work long-term, regardless of age

With the added element of a larger age gap, it is important to ask this question in the context of age, as there are added considerations that come from being in a relationship with someone in a completely different life stage than you. Most obvious among these considerations is the desire or ability to be a parent or where you are in your respective careers.  

Several less obvious driving forces can also direct you into a relationship with a much younger man. Perhaps you are starting to feel your age and want to be around someone significantly younger to feel young again. Or maybe you aren’t attracted to men your age and are drawn to younger prospects. Or perhaps you usually don’t date younger but have found your soulmate who happens to be a few decades your junior.  

Once you understand your reasoning for entering an age-gap relationship, you can navigate that relationship and your expectations accordingly. But you are not out of the woods yet. The follow-up questions you ask are equally relevant, beginning with this next one.  

2. What is a younger man looking for from a relationship with me? 

Since two people have to agree to be in a relationship, it means similar to how you have your reasons for wanting to pursue this relationship, the guy you are considering has his. With that in mind, ask yourself — and him (you might be surprised how brutally honest people can be when posed with a direct question) — why he is looking for a relationship with an older woman. The reasons might surprise you.  

It could be that he is simply “into” older women. Or it could be that he is trying to find a sugar-baby-type situation. Or perhaps he is interested in you for you, and age is not a factor for him. 

Whatever it is, it is important to understand his motivations in dating you so that you can protect yourself. For instance, if you suspect that he wants to date you because he thinks you have money, you either need to be OK with that reality or move on, as financially motivated relationships can be destructive not only to your bank account but also to your heart. 

Additionally, you need to understand his reasoning for being in your relationship because it contributes to compatibility. Even if you are both looking for an age-gap relationship, you may still be incompatible if you have different motivations for being in your specific relationship. 

3. Do I care what other people think and say about me dating a younger man? 

To address the elephant in the room: Age-gap relationships can be controversial. When the woman is older than the man, the relationship may become even more controversial or be judged more harshly. 

Inevitably, you will probably face some judgment for dating a man significantly younger than you. Whether it is from acquaintances who tease you for dating someone young enough to be your son, from strangers who glare at you or roll their eyes at you in public, or from a misguided onlooker who tells you that you and he have the same eyes, people will perceive your relationship a certain way. They may go so far as to express those perceptions to you, mean-spirited or not. 

Such comments may bother you. Or they won’t. The point is that you are honest and ask yourself from the get-go if you care what other people think and say. While we can all express platitudes about how it doesn’t matter what people think as long as you are happy — which is true, and you shouldn’t let other people’s biases dictate how you live your life — it is also true that relationships don’t exist in a vacuum.  

The external pressure of people shaming you for who you love could penetrate your relationship and ultimately apply pressure. If you feel ashamed of being seen in public with your partner out of fear of judgment, your relationship will probably not work. If you know yourself and that this type of judgment will affect you, then it is best to end the relationship now. Going against the grain requires thick skin. 

4. Will I be able to keep up with a younger man? 

Being “older” can be a concern if you and your partner have different energy levels. For instance, if your younger partner is currently running marathons, but you have problems with your knees and cannot walk too far, you may suffer from incompatibility.  

Similarly, you may have issues with sexual compatibility. A younger man may want to have sex several times a week, for example, while an older woman may not have the same needs. That said, generalizations abound regarding age, making this last question a must …  

5. Will a younger man be able to keep up with me? 

Being an “older” woman doesn’t mean you don’t have energy or desires, sexual or otherwise. Quite the contrary. Many single women 50 and over find their stride, exploring new careers, hobbies, and interests with renewed or even a new vitality previously unmatched in their lifetime. 

So just as you need to know what you are getting into when you become involved with a younger man, the same will go for him. A word to the wise: Make sure he can keep up — with you.