The cheat sheet for dating an older woman

By Sasha Fedorovsky

Times have changed and dating a younger man seems to be all the rage! In this particular instance, I’m referring to women in their late 20’s and into their 30’s dating men in their early 20’s. I’ve never found younger men to be that appealing, however the market seems to be overflowing with them and after some inspection *cough* research… I discovered they ‘aint half bad! The older ‘mystery man’ seems to be old news and we single ladies are taking advantage of a younger and fresher approach to romance. There lies plenty of potential in this nevou style of relationship and I’m all for younger men stepping up to the challenge. There is no denying the challenge is a significant one, as the female psyche is a confusing place at the best of times – sometimes even to the female herself!

Having a soft spot for the younger gentleman and understanding the challenges they may face with a demanding *cough* – I mean experienced older women, I’ve come up with a ‘cheat sheet’ on conquering her and feeling like the man in the relationship…


1. Be The Decision Maker

Don’t make her feel like she is your mother, man up and make the decisions. Tell her what, when and where. Do it with confidence and don’t worry too much if she had something else in mind, she will respect you for taking charge. On the other hand if you fail to do this you will loose the power in the relationship automatically and it will be very hard to get back.

The fact that she is older and more experienced will definitely make you a little bit nervous, it’s a very different world from the 18-year old girls that giggle and blush at all your jokes, this one maybe laughing at you. To win her over you will have to work overtime at playing the man in the relationship, primarily because your natural instinct will allow her to take charge. Don’t give in! Play the lead role, even if this means showing a little more chivalry and dominance then you usually would. Being the decision maker is setting the structure that will make her take you seriously and not be left craving for the days when she used to date ‘actual men’.


2. Don’t Put on a Façade

Whatever you do don’t put on a façade of being older or wiser then your years. It is a very unconvincing act and the moment you are with your friends it will be very difficult to balance the two personas! If you don’t know anything about wine, stick to beer. If you don’t have money in the bank yet, don’t go out and finance a hot car, but most importantly if all you really want to do is party and travel the world in the next few years don’t make out that you are saving for a house and planning for the future. Be true to yourself or else you will come across like a big schmuck. Even if she falls for it, her friends won’t be fooled so easily and are sure to give her the heads up sooner or later.


3. Watch Out She Can Almost Read Your Mind

You may have to come to terms with the fact that she will always be a few steps ahead (in the early days of the game at least). She’s dated before and she isn’t hard to fool, so if you are planning to cheat or act shady then plan to get caught. She will also know how to push your buttons and position you in a certain direction, take note and learn quickly. The upside of this for you is that she won’t expect you to know what she is thinking, and will likely spell out what she wants (a leniency older men aren’t privileged to). This is one of the greatest parts about being the younger guy as you aren’t expected to read her mind. She thinks you are too stupid to ever work out what she wants, thus she will get straight to the point and spell it out for you like an Ikea instruction manual.


4. Make The Extra Effort 

Even if you think that your age gap makes no difference because you are rocking her world, think again. In the back of her mind she will be questioning if you are too young for her and if you will really fulfill the ‘potential’ you are showing or if she needs to go out and find herself a grownup. Whatever you do don’t drop the ball, you need to put in 10 per cent more then you usually would to overcome her early day insecurities of feeling like a cradle snatcher. Putting in the extra effort will exceed her expectations and make her think again about how eligible you really are, it will also distract her from the fact that your mum still buys your socks and underwear and that your most serious relationship was back at high school.


If all else fails you will leave with your balls intact as a wiser man, with plenty of stories to tell your friends.


Till next time lovers!


Love S. xox

About Sasha Fedorovsky - S from 'The V&S Show'!