The Baggage of Dating a Widow/er or Divorcee (and how to deal with it)

Dating isn’t easy. Just when you think you have it all figured out, along comes a new twist. Now imagine trying to date after the love of your life passes away from cancer. It’s been almost 7 years since Cory passed away and this is my situation.

After Cory passed, I swore I’d never date again. I felt that love rests with one individual. I couldn’t comprehend going through the pain of losing another spouse a second time. It’d be much easier to stay a widower. I was a young parent and my sole focus was my daughter. Plenty of people offered to set me up but I wasn’t interested. I just wanted my life back to how it was previously.

Then along came Tracy. We’ve known each other since we were babies, coming and going within each other’s lives for years. During the quiet moments since Cory’s passing, I confided in her for advice, thoughts, and companionship. When many friends disappeared because of the painful memories my presence invoked, Tracy stayed.

Naturally we began a courtship and I started taking those little steps. The most challenging moments were at the beginning when I was filled with guilt as if I were cheating. Even though I knew Cory would have wanted me to move on, we never spoke directly about it. I was stuck because I couldn’t accept that it was okay. It was very difficult to let go of that notion and still is today. But I continue taking steps forward.

It’s been nearly seven years and my perception of getting remarried is changing. Part of it is my comfort with Tracy. I sincerely appreciate her patience and understanding of the challenges of dating a widower. The other part is that I learned to embrace the mindset that life has much to offer. It’s up to me to seize life’s opportunities. After all, I want be a better person, a better father, a better companion.

When you’re single without children, dating is a simpler ballgame. The focus is on you and the other person because there are fewer scheduling conflicts. Without children, you have more freedom to explore new waters and endless possibilities without any attachments. There’s generally less drama involved.

Dating a divorcee or widow/er is an entirely different ballgame. The fact that a previous marriage ended unfavorably can have a drastic influence on commitments and emotions. Neither of which are ideal starting points to a dating relationship.. but anything is possible!

Sometimes those who come from divorced relationships are more easily able to finding new relationships quickly. In those cases, the divorce process may have dragged on a for while and people feel as though time has been lost. As a result, they make up for lost time within the new relationship. There’s more of a push to start a new life again and move forward.

A widow/er has a different perception. While some feel the need to fill the void of their lost loved one immediately, most people tend to take their time and are resistant to dating again. The very thought of it is unsettling and upsetting. They experience the same emotions of guilt that I did. And when the prospect of dating reveals itself down the road one day, we react slow as molasses and could take years to materialize. Such is my life.

Dating isn’t easy. Perhaps in the end, there aren’t any secrets and labels are meaningless. What’s most important is that you continue to go about your life exploring.

The future may be unknown and we can’t undo the past, so “keep those feet moving.”

Check out my blog Keep Those Feet Moving to read more inspiring posts.

Thanks for reading —


AJ Coleman