Dating an Older Woman as a Younger Man: Dos and Don’ts

Dating an Older Woman as a Younger Man: Dos and Don’ts
Photo by Tamara Bellis

The age difference is rarely a topic of conversation when the male is significantly older than the woman. When the woman in a couple is older, though, people often give them weird stares. Naturally, this begs the age-old question of what draws a younger man to a lady of a certain age.

It is hard to pinpoint why younger men find mature women so irresistible. But, the trend of young men dating older women is certainly becoming stronger, as is evident on cougar dating platforms.

The prospect of dating again after a long hiatus may indeed fill a single man or woman over the age of 50 with dread rather than anticipation. Thankfully, dating platforms are now available to meet fascinating singles for all sorts of relationships. And these platforms help even if you are looking for a mature woman for the very first time in your life.

With online dating sites, the odds are definitely in your favor. Yet, it is important to remember a few dos and don’ts of dating an older woman.

Understand Their Types

Before going any further, you should know that not all mature women fall into the same category in the dating world. They are from different age brackets and may have different relationship goals. Knowing these types can help you enjoy more success on a cougar dating site used to enjoy mature dating as opposed to sites dedicated to MILFS or sugar dating.

For instance, it is vital to know the difference between a MILF and a cougar. So many people use these slang terms interchangeably, but there are differences.

When you date a MILF, it means you are with a mature woman who is a mother and has children. However, not every mother qualifies as a MILF; in fact, the term is typically reserved for mature women who look so hot and beautiful that it is hard to tell if they are moms. You can encounter some examples among celebrities.

A cougar is a woman at least eight years older than the men she dates and she usually “hunts” the men she likes. Your cougar woman is often between 35 and 55, though she may be younger. Interestingly, a cougar may sometimes be “tagged” as a MILF when she is old, hot, and has children.

On a dating site, you will find MILFs, cougars, and sugar mommas. While sugar mommas are older women like MILFs or cougars, they are rich and willing to pamper a young guy for his company.

Once you have your concepts sorted, you can go ahead and join a dating site and enjoy some success keeping the following do’s and don’ts in mind.

Embrace Your Do’s

For ultimate dating success, learning what you should do when looking for an older woman and how to impress her is essential.

Stay True to Yourself

Do not try to be someone else just to look impressive to an older woman. It makes you feel lost, and a lost boy still searching for himself and his goals is definitely not something a cougar is willing to put up with.

Having your life together to the degree of a “lifestyle guru” is not required. You should, however, be able to demonstrate that you are actively attempting to improve yourself and that you have a clear idea of where you want to go in life.

Understand Her Needs

They have likely witnessed it all, from significant life changes in their careers to conflicts within their own families. It is essential that you understand her journey and learn what she truly desires.

Paying attention to her dating profile is an excellent way to understand what she needs and what brought her to a dating site in the first place. It could be sex, it could be flirting, or it could be something else. Figure it out!

Treat her with dignity, both as a woman and for the experiences she has had. It is actually easier to win over a mature woman when you show her proper respect and affection.

Make Her Feel Comfortable

Do not push her to make a decision the moment you start chatting with each other. Even if both of you are looking for a casual hookup, give her some time and space to react.

Listen to her. Find out more about her passions and interests. Make her talk about those things. Invest extra effort into making her feel loved and young again. They expect this from younger men, and you certainly do not want to let them down.

Avoid Your Don’ts

Do not spoil it for you just by not paying attention to things older women hate. So here are the “don’ts” you need to remember.

Do Not Pretend You are Too Experienced

It is okay if this is your first time dating an older woman. Be honest about it, and she will love you more for it.

Do Not Come Off as a Shallow Person

If you pursue her only because of her age, you come across as a shallow person, which is a huge turn-off for older women.

Do Not Act Hard to Get While Flirting

It is okay to play around and not look desperate for mature love, do not make them chase you, especially on a dating site where they have hundreds of other options.


Do not bash yourself for being in love with mature women; they are so irresistible that men around the world share the same love. Just be sure to use the right dating site and understand the do’s and don’ts to score big with mature ladies.