Dating As A Widow

May 6, 2025

I was a widow, I just lost the love of my life, and dating was not on my radar.  Before, my love Jeff, passed away, I stated that I would never want to enter the dating world.  I felt that I had lived a fairytale with Jeff, our love was magical, so there was no need to be on the dating circuit or look for love again.  As a young widow, I was healing from the painful loss and learning to build a new life without my love.  At times it felt paralyzing, but I moved through the pain and was determined to discover who I was without Jeff and find joy again. During my healing and self-discovery as a widow, I noticed pockets of joy and laughter returning to my life; it had been a long time, and it felt refreshing.  Then one day, unexpectedly, during the healing journey, it was as if a light switch was flipped when I least expected it and I decided to try dating again.  The thought was exhilarating and terrifying.  I hadn’t been dating since my twenties, now I was a widow in my early fifties looking for a committed relationship and hopefully love. I was optimistic that love would find me if I kept my eyes and heart open in this new uncertain dating world of online apps.  This was all new to me, and a bit unnerving.  Some of my concerns were things like safety in online dating, but also the idea that there would be some unscrupulous men that would attempt to take advantage of a widow, as they can be typically more emotionally vulnerable.  With this in mind, I kept my guard up and leaped into the dating world with my children’s blessings.

In some of those early dating conversations, I found it difficult to talk about being a widow. While the wounds that gave me that title were becoming less raw, and I acknowledged and accepted the term widow, this whole experience was new—dating in my fifties as a widow felt like uncharted territory. I wasn’t sure how much to share or leave out about my life and the love Jeff and I had. Yet, over time, I became more comfortable and discovered that dating could be a fun and adventurous journey. This new world of online dating came with its share of bloopers and men I had to block, but overall, the dating experience was exciting. Although I still missed my love every single day and my love for Jeff will never end, I was learning to embrace widowhood at such a young age, something I never anticipated would be my reality. I also grappled with guilt as a widow. I wasn’t trying to replace Jeff or erase our past; I would always carry our love in my heart. I knew that emotionally it would take time in the dating world to balance my past and future as a widow. I realized that finding new love doesn’t mean letting go of Jeff’s memories; instead, it’s a way to move forward, create new possibilities, and find happiness while still carrying my love’s memory with me on this journey. 

I understood that some outsiders might always perceive me as a widow and may not support my dating after losing my love. However, I recognized that prioritizing my happiness was essential, rather than worrying about what made others comfortable. 

Although it was challenging, I did my best to avoid comparing the men I was dating to Jeff.  As a widow, I needed to adjust my expectations and remind myself that my love for Jeff would not be the same with anyone I was dating, and comparing anyone in my mind would not serve me well.  I viewed this as an exploratory period in my life where I embraced my new role as a widow and appreciated the vibrancy that a new relationship can bring. 

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