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  • Writer's pictureDeborah Holmén

Navigating Love After Loss: Essential Advice for Dating a Widower

How the complexities of dating a widower are not for the faint of heart.


By Deborah Holmen, M.Ed., NBCT, Previously published

Couple embracing on the beach

I was approached by a Widowhood group online to share my experiences dating a widower. A member of this group was struggling with whether to stay or leave the relationship, and it was eye-opening to hear the members' struggles. I came up with these tips to help them understand the complexities a bit better.


Experience is the best teacher, and after almost nine years, I've learned some valuable lessons about dating and marrying a widower.


If you're not prepared to love unconditionally and accept that people may sometimes prefer the alternative, then maybe dating a widower isn't for you.


Here are some tips to help you navigate the intricacies of this unique relationship and create lasting happiness.


The Outer Circle of Friends Will Be Happy For You

When I met my future husband nine years ago, three years after his late wife passed, I had no idea what to expect.


It wasn't planned; we met at a Saint Patrick's Day event we both reluctantly attended for our friends. Our stories of that night differ because we were in different places in our lives—he was re-entering the world of the living, and I was preparing to move back East as a single mom sending my daughter to college.


Despite our different paths, we became inseparable a week after our first date. It was like living in a Nora Ephron film, romantic and heartwarming. He was ready to live again, and his friends were thrilled to see him happy.


They knew how much he had struggled with losing his beautiful life partner, and their genuine happiness extended to me as well. However, there were some friends who needed coaxing to embrace this new normal. Grief is a tricky emotion, and it can surprise how it rears its unflinching head.


When dating a widower, you'll find that friends who understand the intimacy of grief will likely rally around both of you. They were genuinely happy that he had found someone, and ultimately, they understood that no one deserves to be alone.


A Ghost Amongst the Living

Dating a widower comes with its own set of challenges, the most significant being the presence of an unseen entity—not just in the home but in the hearts of everyone you meet.


Some of my friends assumed dating a widower would be easier than dating a divorcé since there was no ex-wife to contend with or alimony issues. But the reality is that the emotional complexities can be insurmountable if you're not prepared.


  • Embrace the photos and stories as a way to learn about the late spouse, their relationship, and family dynamics. Think of it as a stroll through a museum of his heart. By asking questions, you understand the influences and perceptions of all around for a fuller and richer experience.


  • Don't take the reminiscing personally or compare yourself to the lost loved one. Comparing is a trap that prevents personal growth and understanding.


  • Take a walk on the spiritual side! Here's an unexpected tip that helped me immensely. I "met" his late wife through a medium friend. About two months into dating, I spoke with Mesina from Psychic Whispers, a medium I met while researching a manuscript. During our conversation, his wife popped in to say hello. Whether you believe in the "other side" or not, it brought me peace knowing she was aware of my presence in their lives. Mesina described her as angelic and peaceful, validating her presence with a funny recount of my struggles learning where he kept things in his home. His wife shared that he wasn't meant to be alone and was happy he found someone she approved of. This was crucial in understanding my boyfriend's grief and his friend's efforts to bring him back to life.


Accept What You Can't Change - But Find A Tribe!

Here's the hardest advice: You will always be Plan B.


My sweetheart makes me feel special every day, but some family members may never fully accept you, especially if they're in a different place in their grieving process. They might accept that their father or grandfather should be happy, but you'll never truly be part of their inner circle.


This becomes evident during special family events. Don't feel slighted if you're asked to step out of a photo or not invited to an intimate affair. Understand that you represent what can no longer be, and that's a hard pill for some to swallow.


What helped me through this process was understanding that each person has a level of emotional maturity, especially during trauma.


Emotional maturity helps us cope with difficult situations life throws at us and isn't necessarily related to age. It helps us manage and understand our emotions, especially during trauma.


Finding your tribe is crucial. I was lucky to connect with several of his friends who understood that life changes and we must accept it. They became my support system, reassuring me that I am a good person and that I matter.


Every relationship is different, and so is your willingness to accept certain things. If you're struggling in your relationship with a widower, find your tribe, learn about the grieving process, and embrace the journey of life with all its different paths.



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