5 Questions To Ask Yourself Before You Start Dating A Much Older Man!

Remember when you were 16 years old and had a crush on that guy who was 19 years old who worked in the local petrol station? Back then the 3 year age gap meant nothing, if anything it made him even cooler (if that was even possible) in fact, had he asked you could have easily pretended to be 18 years old if 16 was going to be an issue. I mean, it’s not like you didn’t look 18 – you wore lipstick, perfume, tight jeans the lot!

So you go through your 20s dating men a few years older than you because you realise that for the most part, men who are younger than you, well in many ways they’re still pretty much teenagers and you really don’t have time for immature nonsense.


Men in their early 30s are also an attractive prospect as you suspect they have their life together and may just be ready for a committed relationship? However in your early 20s’s quite often the idea of dating a man older than 39, just wrong seams… well-wrong! He’s old and may have grey hairs- you know, down there; and you figure he’ll definitely have a marriage and child/ren somewhere in the equation and you really don’t need the drama or a man so set in his ways there is no room for change.

Then you get into your 30s and start to find the attention from men much younger than yourself rather flattering; it means you’re still looking hot and definitely don’t look your age but you’re not quite a milf or a cougar. Except now the dynamic has slightly changed and you get irritated if men in their 30’s by pass you for a younger model, and all of a sudden you find yourself looking at men 10+ years older than you as totally viable prospects.

So what happened?

Somewhere between 28-35 the maths, the dynamic and the expectations change and the idea of kissing a man who looks like George Clooney or Robert Downey Junior become as turns you on, rather than makes you want to throw up and go looking for the nearest 26 year broke musician you can get your hands on. We often become more confident as women with age, despite the issue of ever depreciating youth.

So what happens to women 30+, in what I like to call the  “beginning to feel comfortable in my own skin years”; especially those who have never been married and may have yet to experience motherhood?  Well by some anomaly, they often start to consider and actively engage in dating men significantly older than them; that’s if they don’t swing in completely the other direction and start taking up with men 10 years younger, which personally sounds like a living hell to me. However,I have known friends do it quite successfully stating: “he keeps me feeling young”.

But how do you decide your bench mark for dating an older guy ? I mean how old is really just too old…

5 things to consider before taking up with a much older man:

1. Has he been married and does he have children? If the answer is yes, at least you know he’s relatively normal, but it’s important to see what type of relationship he has with his “ex- family”. If the man is on amicable terms with his ex-wife and great terms with his children, that is a good sign. If his ex and kids hate him then you should wonder why? If the answer is no, it’s worth asking him why as maybe he is a confirmed bachelor; is this what you really want?

2. What is his relationship like with his work? By this I mean is he a workaholic? Many women find that after dating an older man for a while, they discover that the only thing he is really committed to is his job and toping up his 401k. It’s important to see whether your ‘potential new man’ already has a healthy work/life balance in place.

3. What is his outlook on life? Whilst you’re probably not after a man who still wants to wear a beanie hat and low slung jeans at 46 years old, my bet is that you’re still after a man who is young at heart and who takes care of himself physically and mentally?

4. Does he actually have a life? If your 33 with your own friends, interest and things you enjoy doing that you plan to keep doing even when you’re in a relationship. Then hooking up with a 50 year old man who wants to now spend his every waking moment with you will soon become suffocating. He should have his own friends and his own interests, but hopefully be over nightclubbing with his mates every Friday and Saturday night, after all – you are!

5. Can he please you in bed? Yes, older men tend to have more experience, patience and can easily make much more skilful lovers than your average’buck wild’ 24 year old who can’t really get over the fact that he is seeing you naked to actually do much about it. But there is also the issue with decreasing virility and stamina as a man ages. If you still plan to be sexually active for quite a few years yet, it’s important to ensure that your partner is sexually compatible with you, no matter what age he is. If he is already experiencing virility issues you may want to rethink whether you are ready to get into a long term relationship which may not meet your sexual needs quite shortly.

These may all seems like common sense things, but quite often women can overlook some of these key factors especially in a situation where their own biological clock may be ticking, or they’re scared they may never get married and end up ‘that women’ who is over the hill and on the shelf!

Deciding to enter into a relationship with someone is an important decision that should not be taken lightly regardless of their age or yours. But if you’re considering dating a man 10 or more years older than you and are already in your 30’s or over; then these are all factors that you really do need to take into consideration before you become his “ girlfriend” or possibly his wife. You should also consider using a public records search to get more information about them. Even though that might not give you the answer to every question we mentioned above, it’d certainly help you to find out if they have any criminal history or legal issues that you should be aware of.