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A Dating Guide for Senior Men


Whether you’re a divorcee, a widowed man, have never married or even been in a committed relationship, you may someday decide that you are tired of being alone. I completely understand. You see, I’ve been in your shoes as have millions of other men. As a result, there are many useful lessons and best practices for you to learn from as you emerge from the shadows of your life. So I have compiled a list of Dating Tips for Senior Men. To start, all you may desire is a companion, even if it’s only to have someone to complain to about the weather or our government or to have a casual dinner with occasionally.  If things go well, your new relationship may have even more significant potential.

Dating tips for Senior Men

Men have various reasons for wanting a new friend.  Some men hope to discover love while others are happy having someone who can cook meals or perhaps take care of them should they ever become ill. Others are just lonely and desire someone they can share a bed with them.  Yes, like the women they seek, men too have their motives.

Some men are desperately lonely, usually the result of a divorce or the death of a spouse.  Still, others are wounded following an unwanted breakup or a bad previous romantic experience; causing them to be frightened at the thought of exposing their emotions, not to mention their wallets to more pain. As a result, they forego any future entanglements. To them, it’s just not worth it.  Still, others see a real upside to dating and are willing to give it another try. Good for them.

Dating Tips for Senior Men

But gentlemen… go slowly.  

There are many risks associated with late in life dating. From the emotional dangers of rejection to the financial risks presented by a predator woman, dating has its downside.  But that should not deter a single or widowed man from seeking a companion or more. Dating is exciting. It’s fun. So don’t miss out if this is what you desire. Dating can complicate one’s life, so be sure to seek the sage advice of your trusted family members, friends, and advisors, and go about it with your common sense fully engaged.

Where does an eligible man begin?

If you are considering re-entering the dating scene, you first need to understand your own motives clearly. What is missing in your life; a life partner or a hot date? Do you seek the companionship of a woman of deep faith, an intellectual who can debate the issues of the day or someone who can make you laugh and has a great figure? I know, I know… you want all of the above. But what are your MUST WANTS?  No matter your wants, it’s good to make a list of what is important to you and then concentrate your search in the locals where you are likely to find them.

If you’re reading this article, you are likely of the vintage where you have accumulated baggage.  It is also fair to assume that anyone you may hope to have a relationship will come with some baggage too.  New romances can become complicated yet still rewarding and worth exploring. And when you do, you are likely to want to move things along pretty fast, but you would be better advised to be a bit more patient. Men can be impulsive, a character flaw that triggers potentially devastating errors in judgment. Relax and move forward but do so with intent and purpose.  

Following the passing of my wife in 2008, I came to the point where I wanted a companion. I did my research and eventually tried the online dating service, Now when you speak of dating services, be aware all are not created equal. Fortunate for me, eHarmony paired me with a computer engineer named Maria.  Maria used eHarmony because she happened to know the psychologist that designed the matching software used by eHarmony.  He confirmed how the engineering that drives eHarmony was scientifically valid.  I suspect not all online dating services can make the same claim. Maria and I were married a year after our first meeting on a cruise ship off the coast of Italy. Needless to say, I endorse eHarmony, but I have also read good reviews about other online dating services so shop around and do your research.  


Regardless of your circumstances, I want to encourage every man to seek the joy and rewards life has to offer.  When I was young, my mother once said to me, “If you want to meet nice girls, go to church!” Regardless of your religious beliefs, my mother’s advice is worth considering too.

A Dating Checklist for Senior Males

  • Know yourself

      • What void in your life are you attempting to fill?
      • Are you emotionally ready to share an evening or the rest of your life with someone special?
  • Identify your Must Have or Never Want

      • Children? A smoker/drinker? Someone younger/older? Someone healthy or likely to need a caregiver soon? Someone who may need financial assistance or is self-sufficient?
  • Clean-up

      • Women prefer men who take care of themselves physically as well as visually.
      • Don’t invite a woman back to a cluttered or messy home.  
  • Define your strategy

      • Blind dates.
      • Online dating service such as,,, etc. If you use an online service, be honest when completing their questionnaire.  
      • Join groups or volunteer where you are likely to meet others with common interests.
      • Tell your friends and family you are open to meeting someone.
  • Get off the sofa

      • Be where people are found; civic and public events, at a house of worship or by joining clubs.
      • Get a part-time job where women will need to interact with you.   
      • Avoid bars.  
  • Be honest about your intentions

      • Don’t say you’re the “marrying type” if you are not.
      • Be sure you can spend time getting to know one another.  Doing so in the dark confines of a movie theatre is hard.
      • First dates over lunch at a favorite restaurant make for a safe environment for both parties.
  • Enjoy the moment

        • Plan for dates that both you and your new friend will genuinely enjoy.
        • Be Some of the most enjoyable dates don’t have to cost anything.  

    Herb Knoll is a retired banking executive, an advocate for Widowers, a professional speaker and author of the breakout book, The Widower’s Journey. Herb is the founder of the Widower’s Support Network featuring the Widowers Support Network – Members Only, a private Facebook group page for men, and a second Facebook page which is open to the general public at Widowers Support Network.
    Contact Herb at 


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