This INTRO section gives you a high-level overview and introduction to the types of issues discussed in the rest of the Midlife Dating Advice section of  The purpose of this Midlife Dating Advice section is to enable us (the midlife bachelors and sometimes midlife bachelorettes) to share and leverage the midlife knowledge … so that together we can more easily maneuver our way through our individual midlife bachelor/bachelorette experiences.

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Introduction to the Challenges of Being Single at Midlife
Midlife bachelorhood brings about many new challenges for those of us who are often rather secure and comfortable in the other non-relationship aspects of our lives.  Many of us at our age have very stable professional lives … and some of us are also fortunate enough to have also achieved a measure of financial success.  However, entering or re-entering the dating world at midlife can be a huge issue for a man of any means to face, as it can be very difficult and uncomfortable – especially after having likely gone through some level of trauma or drama associated with the breakup of a long-term relationship.  You can feel like a “fish out of water” … like you are lost.  I’m here to tell you that you are not alone … that there is hope … and that the midlife bachelor journey you willingly or unwillingly are about to embark upon is going to make you a better person overall.

Some of us are midlife bachelors by accident – others by design, or even by nature.  Midlife bachelorhood can sometimes happen quite suddenly – maybe you go home one day, and discover that your wife has cheated on you and is leaving you for another guy.  In other cases, you might see midlife bachelorhood approaching as you experience your long-term marriage winding down – as your mutual interests with your wife change and grow apart slowly.  In yet other instances, midlife bachelorhood can appear to be a systemic or perpetual issue – like the forty-something guy who has never been married, or who cannot seem to get a date (or maybe a second date).  No matter what the cause or the circumstance that got you here – midlife bachelorhood represents a significant OPPORTUNITY for personal growth in many ways.  I emphasize the word OPPORTUNITY because essentially that is what midlife bachelorhood brings you … an opportunity to take a completely fresh look at yourself, and make some adjustments that will set the stage for your own happiness over time.

Do all midlife bachelors need to make adjustments?  What if you feel the reason for your midlife bachelorhood is not your fault – rather you feel it is the fault of your wife or ex-wife?  That may or may not be true – but the point is you are here … you are a midlife bachelor … and no matter the reason, you now have a starting point in common with many other of our midlife bachelor brothers.  Every single one of us faces some fairly similar issues – how to re-enter the dating world, how to maximize your chances of success, and how to minimize our mistakes.  One objective of this website is to leverage the accumulated knowledgebase of many midlife bachelors so that all of us can learn and benefit from the successes and challenges of others in our situation.  This initial knowledge base is composed of what I’ve personally learned, along with what many of my friends in our age bracket have experienced.  Keep in mind that dating is not the only issue we as midlife bachelors face – sometimes there can be other issues … issues related to getting older … like baldness, or obesity, or (gulp) erectile dysfunction.  No matter the challenge, the key to success and happiness is preparation … thinking things through, and developing a solid strategy.  To answer my initial question – yes, every single midlife bachelor needs to make some sort of adjustment.  No one is perfect.  And even a Ferrari needs a tune-up once in a while, right?

Bachelorhood is something that has woven itself into and out of my own life periodically over the years.  After marrying relatively young at age 23, I found myself divorced several years later.  And since then, I’ve shied away from marriage – and instead experienced essentially a serial string of short- and long-term relationships.  With each passing year, I have learned more about myself, and (I believe) more about women.  Now at age forty-two, I often find myself being the go-to guy for many male friends and acquaintances of mine who have recently become single – and who find themselves lost (or maybe at a loss?).  Listening to them – and learning from both them and from myself over the years is what composes the knowledge base that I draw from in putting together this for you, the midlife bachelor.  I don’t claim to know everything – not by a long shot.  I do, however, consider myself to be someone who listens to people, and observes.  I believe my personal gift is my ability to communicate much of what I’ve learned to others.  And you should not ONLY listen to me … you might consider joining our  Midlife Dating Forum, where many midlife dating topics are often discussed.  We have both men and women that participate. Click the link, or on the graphic below to check it out.

Check out the Midlife Dating Discussion Forum!

Why bother writing about any of this?  Actually, there are many compelling topics on this site that I wish I had the opportunity to read about in the context of midlife bachelorhood.  Let’s take ERECTILE DYSFUNCTION, for example.  This is a topic that no one talks about.  None of my friends has ever asked me about it, nor is it one that I’ve brought up with them.  Yet I know it is an issue for some percentage of midlife bachelors because it became an issue for me!  ‘E.D.’, as it’s called, has such an awful social stigma that men fear it … men deny it … and often avoid the topic at the expense of everything, until it eventually becomes undeniable.  If you think you may have a problem with ERECTILE DYSFUNCTION, stop reading here – and go immediately to the section of this site entitled Erectile Dysfunction – Suddenly The Man you Once Were is not the Man You Are Now  After you’ve read that section, finish reading through the remainder of this Midlife Dating Advice section – but start the process of dealing with your E.D. first.

E.D. is certainly one of the scariest issues that I’ve personally had to deal with – but that is just one of many possible physical and social dilemmas that we face as midlife bachelors.  Dating is really the most common issue we face – at least initially.  Successful midlife dating is generally composed of a process or a sequence of events that must be executed in a certain relative order.  For some men, it all comes quite naturally – but for many of us, it is often much more of a deliberate procedure.  The really good-looking guys have it easy – as women generally (or almost literally) simply fall into their laps.  The same can be true for celebrities or for the very obviously rich men.  These guys can do or say whatever they want, and the women still trip over one another to be with them.  It is easy for the rest of us to be jealous of these rich or good-looking guys – but let’s step back a moment, and look at the big picture.  Rich or extremely good-looking men are much more likely to either cheat or to be abusive (mentally and/or physically) than the rest of us.  They do this BECAUSE THEY CAN … since they can quite easily go out into the world, and find a new woman in no time.  The fact that women chase these types of men may reinforce one of my “Fundamental Truths about Women” – Women are Crazy!

For the rest of us “average guys” who find ourselves single in midlife, it takes more effort to just get a date … and often involves some prep-work to get to the unfamiliar and uncomfortable point of being able to ask a woman out.  You’ve first got to take a look at yourself, and determine if you need a makeover.  This doesn’t mean getting a facial or makeup – it means taking an honest look at yourself in the mirror, and figuring out what you can do to maximize your appeal to the opposite sex.  I go into a lot of detail on this subject in the section entitled, “The Midlife Bachelor Personal Makeover“, but basically you might need to go through what I call a ‘personal revision’, and do a Rev. 1.1 or Rev. 2.0 of yourself.  This could include sprucing up your wardrobe, getting a newer hairstyle, shaving the mustache you’ve had for the past twenty years, getting rid of that beater car you drive, stopping smoking and/or drinking, getting in shape/losing weight, whitening your teeth, … the list goes on as there are a lot of possibilities depending on the condition you are in.  It might at first seem a little silly or superficial, but remaking yourself is absolutely one critical determinant of how successful you will become as a midlife bachelor in the dating world, as it contributes to your self-confidence as well as your appearance.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.