Older Women Dating Younger Men: A frank, honest comparison of the Pros and Cons

To Date or not to Date?

Dating an older woman can be the stuff of fantasy. Not having to pay for anything, having the status of a young boy toy, being with a woman who is experienced in the bedroom… The truth is the reality is not always like this. Often this situation only gets played out in our heads or in movies. The reality is there are many factors that must be considered by the modern gentleman before deciding to date a significantly older woman.

Here are the pros and cons in dating an older woman.


An older woman is more often more independent, knows what she wants in life and has an established career. She will be selective about when she spends time with you, which means a relationship where you will have more time to do your own thing. She will be less ‘needy’ and understand the importance of quality vs quantity.

An older woman is more experienced. This is a great thing as there is always much to learn about culture, wisdom, and all that other good stuff that only an experienced person can have. You will find yourself less at the local pub on a Friday night, and more at classier places like nice restaurants and the theatre. Expect the intelligent conversation to pick up.

An older woman has career experience. This translates to a lot of useful wisdom and tips with regards to your own career. Often, there are better networking opportunities through her colleagues and friends than there would be with a younger woman.

An older woman is less likely to ask you to pick up the check for dinner. She will have her own money, be more confident in her self and is less interested in ‘traditional’ date behaviour like that gentleman picking up the check.


An older woman may be looking to get married sooner rather than later. Dating is ultimately the search for a permanent partner, and an older woman is more commonly looking to settle down faster than a younger one.

Does this older woman have children? This is something that all young gentlemen should consider. Can I have the time, responsibility and genuine effort it takes to raise children that are not mine?

A divorced older woman may have baggage. Often marriages end bitterly, and it is important to fully understand if she has left behind a resentful ex husband that may be looking to rip your head off.

It is known that mentally, a man matures later than a woman. By dating an older woman you are bridging the ‘mental’ gap further. What this translates to is that an older woman’s tolerance for loutish behaviour would be lower than a younger woman. Gentlemen, good behaviour is absolutely necessary.

Yes, there are cougars out there. Although it is great to feel desired sexually, the pay off may be a feeling of lack of respect or not feeling like the ‘man’.

To date or not to date?

I would say, when dating an older woman the relationship should be built on honesty and communication. As long as both parties are completely honest about their intentions and expectations then there is no reason that a relationship like this cannot work.

Obviously, situations differ with each individual and what might be true for some may not be true for others. My sole interest in writing this article (and others) is to assist people in finding relationships that are happy, and not to make generalisations or cause offence – AMG