DATING AGAIN?
As we become widowers, many of us struggle with the question of “if” and “when” is it appropriate to start dating? Some of the things we are fearful of are:
making unforgivable mistakes,
embarrassing ourselves,
being taken advantage of,
offending children, family, and friends by dating too soon.
This can lead to a long difficult internal discussion about the wisdom of ever dating again, much less next month. This is just one article I have written about this difficult topic. If you are reading this, you probably have been thinking hard about this. I do recommend that you take your time to consider whether it is the right decision for you, even though your body and mind may be screaming for you to jump into dating, right now!
Once you have decided to date again as a widower, prepare yourself for the shock of entering a dating scene that has changed dramatically since your younger days.
I only decided to date again after an emergency hernia operation that led to my desire to re-engage with life again. A humorous incident that included an untimely infatuation with a young dental hygienist (see my book for full story) prompted me to see my therapist, who then advised me to consider dating again… And soon!
This led me to sign up for Match.com and other websites to place myself on the market. Filling out the bio, interests, and desires for possible matches, as well as providing a photo, was a mentally challenging experience. You want to be honest, but let’s face it, our self-image can be terribly skewed either for or against ourselves after losing our wives. You want the biography to put your best foot forward while not distorting the truth. If you are going to sit down with someone over a cup of coffee, they will quickly figure out if you lied.
And photos! Try finding a good photo of yourself that is current without hiring a headshot expert. Eventually, I ended up taking several self-photos to get one I liked. As you will find out, many online-dating participants give up and use photos that are clearly outdated. This becomes obvious when you meet them. See some television series such as “Later Dater” to better understand how awkward this can sometimes be for both parties.
I discovered that many women in wealthier areas (Boulder, CO in my case) often spent over a thousand dollars on photos and biographies for their online dating page. (My book delves into detailed tips for online dating) Sometimes the biography sections sound like a fantastical story.
Knowing that my emotional and physical states were fragile at best when I started dating, I decided to seek a woman who came across as nice, but not challenging. In other words, I was not looking for the hottest, youngest, and sexiest first date. More than anything I just wanted to find out if I could date again while enjoying myself and maintaining my balance.
I was fortunate as the first woman to approach me was the perfect first date. We met over wine and cheese after she got off work. The conversation was surprisingly easy, my physical discomfort (arousal) was minimal, and emotionally I felt in control the whole time.
This encouraged me to seek more dates, which led to a period of “binge dating” (something that other widowers reported to me as happening to them as well). I was fortunate to have several “get acquainted” dates with six different women over the next two weeks. With each date my self-confidence, my ability to control my physical reactions, and my comfort with women in a dating environment grew steadily. Though at times exhausting, dating provided me with many benefits, including distraction from dwelling on my loss, a chance to re-engage with life, self-esteem, and most importantly, the female companionship I so desperately wanted.
My experiences with the dating scene helped prepare me for when I met someone special who I am still with eight years later. Because of my prior experiences I was in a much better psycho-emotional state and was more understanding of what a new and good relationship would look like now that I was over 65 years old, and single again.
After meeting many other widowers in my role as founder and facilitator for men’s grief groups, I now know that not all widowers are as driven as I was to re-enter the dating scene. However, many of them are, and the fear of it will often discourage them from taking a chance.
One acquaintance of mine was very fearful of reentering the dating scene and was disappointed when responses to his website page were minimal. However, after some sprucing up, improved photos, and encouragement from others he tried again. This time he met some wonderful women and eventually relocated with one of them.
I can only say that for me it was an early and important step to emerging from the deep dark grieving in which I had found myself submerged. And I know many others who would say the same.
For that reason, I encourage my fellow widowers to give it a try when they get to the point where they are willing to take a chance. Good luck my friends.
© Copyright 2025 Fred Colby
All rights reserved
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Fred Colby is the author of:
Widower to Widower - available through most booksellers and libraries.
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