Dating Advice for Older Men

This week’s offering is more educational in nature. I apologize immediately to many of my colleagues who have reached that point in their life, where they are comfortable with their acquired knowledge and no longer feel the need to learn anything new.

The target audience for my little tutorial on the mature dating world is for the small subsection of much older adult males who find themselves in the peculiar position of spending weekends alone. They are spending weekends alone because they have somehow, through absolutely no fault of their own, and the occasional secretarial dalliance, find themselves chronically single. The advice your are about to receive will fundamentally change your personality, your look, your approach and most probably get you on next year’s cover of People Magazine when they release their “Sexiest Man Alive” issue. My counsel is directed specifically to hetrosexual males though, as with most of the wisdom I share weekly, my advice tends to have a certain universality to it, and more than likely will appeal to all adult single genders including Bruce Jenner.

As we all learned, most successful people spend 90% time preparing and 10% presenting. I will up the percentage to 100 % preparation as I painstakingly prepare you for memorable first dates.

Preparing: There is much to do as you prepare for a first date, and to help you I ask that you pay particular attention to the themes here. I have shamefully stolen most of the ideas directly from the multiple dating sites that are readily available to single people around the world. I have categorized what I believe to be essential topics to help you master the art of preparing for the adult version of a first date.


It seems most of the dating sites out there want adults to introspect and communicate within very strict guidelines and describe in great detail, who they are. This journey of discovery use to happen on actual dates, but now you can eliminate that painful step by making stuff up about yourself, so first dates can still be a time of discovery, however the discovery is now about how inaccurate your profile is. So lets start…


Under occupation simply put astronaut.


Capture how much you like children even if you don’t. The truth is we all like children… except your own.


You have two choices here. 1. Yes I like to pet. 2. I enjoy cats, dogs and giraffes. Ensure you mention giraffes, so you don’t eliminate the taller single ladies from your dating world options.


Some more progressive sites insist you declare your current income. Once again you have two choices here. 1. Filthy rich. 2. Filthy and rich


I workout seven days a week, I volunteer to multiple charities, I paint, I play violin, love to cuddle and I love gazing at the stars, though because I am an astronaut, I get a much better gaze than you do.

Note: Do not put fishing as a hobby even if it is the only hobby you have. The graphic visual of sticking a hook into the eye of a poor innocent worm tends to turn a lot of women off. This may disappoint you, as you don’t get to expose your skill as a master baiter, but trust me, this is an important skill to avoid in your profile.


I am only interested in making the world a better place to live.


Within 27 years of what your birth certificate states or the birth certificate of a very close friend.


6 ft. 2 in.


I can’t weight to meet you.

Now the tricky part comes when they ask you to write a brief description about yourself. Again the most important thing to do here is reflect on your life, consider the joys and the pain you have experienced, celebrate your greatest personal achievements, and then make something up. Let me help.

Let me expose myself, I mean let me describe myself a little. I enjoy long walks on the beach, but not too long as my feet tend to get itchy with all that sand. I love sunsets, but only at night. I enjoy quiet romantic dinners, where neither of us speaks but we communicate through miming. People say I am a great listener, or I think that’s what people say, as I tend not to listen to most people. I am considered very handsome, which is why I am not comfortable posting a picture, as that might intimidate you. I am looking for my soul mate but will settle for my coffee mate. Allow me to paint a little picture ( as I do like to paint; see hobbies) on what our first date together might look like.

We meet in a coffee shop where the stringed quartet I have hired, plays Vivaldi and some Nickelback. As we sit and talk about me it begins to gently rain. I glance and notice you don’t have an umbrella so I offer to rent you mine. As the perfect date winds down you suggest that I come back to your place, but I say no because I want to get to know you better. Of course you insist because I am the best thing that has ever happened to you. I propose a compromise, because men are so good at that. We go to your neighbour’s house, as they are out of town, and gave you their key to feed their pets. We feed the giraffe and then drink all of their expensive scotch, and I pass out on their nice leather couch. Life is a journey not a destination, so you call a taxi, to ensure my journey ends at another destination.


There is much pre-work to do as you make your final first date preparations. Time is not your friend so I will focus on just the important stuff here.

Cuddling: Since you have already mentioned this in your profile you better show some level of competency as this will be a deal breaker. To use the sport’s metaphor, 110% of current female profiles support the idea of cuddling on the couch while watching movies. I share this because men are visual and women are smart. Men do not read profiles, but just stare at pictures because men are visual and woman are smart. I repeated that line as I have no pictures to make my point. You must be a good cuddler and that status can only be achieved with rigorous rehearsal. I strongly suggest practicing this with your sister while watching the movie The Notebook repeatedly. This practice will separate you from your male competition. If you do not have a sister, rent one.


It is important to look good and make a favourable 1st impression. Take a good look at yourself in the mirror. If you do not own a mirror a long strip of heavy-duty tin foil should do. If you are slightly overweight, there is no time to diet and exercise. You can hide any imperfections by simply wearing larger shirts that are not tucked in. This mysterious dangling of fabric over most of your body will entice woman with a sense of mystery to your body shape. Woman love mystery!


Well it’s almost date night so this is the final piece of advice. Find a local plastic surgeon, make an appointment for a free consultation. To prepare for that medical conversation, ensure you bring picture clippings of Johnny Depp, Matthew McConaughey and George Clooney. Now your resemblance to these male heartthrobs is not relevant as a skilled plastic surgeon, should be able to transform any normal face into your choice of this holy trinity of men. A very skilled surgeon will select the best parts of each of these three men and you will be transformed into a multiple celebrity look alike, and there is a thriving business for that kind of look. Changing your legal name to Johnny McClooney is an option you might give some serious thought to, as you are now ready for a magical first date.   As with all great ideas there is a down side to this suggestion. You may find that your physical appearance may become more important than your personality to the prospective dates. This is where the years of intensive astronaut training will serve you well, as you appreciate and adapt to the gravity of your new situation.

So there it is, you are now fully prepared to get out there in the scary adult dating scene, and make memorable impressions with all you meet. By just reading this little tutorial you are now ready to stun your next first date. I can’t promise you any second dates, as my focus here was strictly for your preparation of first dates.


The Blong

I wrote this song as a tribute to all the bad dates of my youth.  Speed dating on steroids.



2 thoughts on “Dating Advice for Older Men

  1. Laughed out loud during this blog especially loved the Nickleback comment – excellent choice!
    Also loved the broken heart story

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