3 Pearls of Wisdom Dating A Widower

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

Deborah Holmén
Change Becomes You

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Couple holding hands on beach facing each other.
Photo by Joanna Nix-Walkup on Unsplash

If ever there is tomorrow when we’re not together… there is something you must always remember. You are braver than you believe, stronger than you seem, and smarter than you think. But the most important thing is, even if we’re apart… I’ll always be with you. ~ A.A. Milne

I waited almost seven years to write this since experience is the best teacher. If you’re not prepared to love someone unconditionally and embrace the fact that people will always prefer the alternative, then maybe dating a widower isn’t for you.

Here are three tips that might help you overcome the intricacies of this unique type of relationship and create new lasting happiness.

1. The Outer Circle of Friends Will Be Happy For You

This was my experience when Rich and I met six years ago, three years after his wife passed. It was also the first time I dated a widower.

It wasn’t planned when we met that night.

Neither of us wanted to attend Saint Patrick’s Day festivities, but we both rallied for our friends. We each tell the story of our meeting a little differently, but that’s because we were in two different places in our life.

He was reluctantly pulled back into the land of the living by a dear friend while I was preparing to move back East to start a new life, sending my daughter to college.

Photo by Kelsey Knight on Unsplash

No matter whose side you heard, we were both intrigued by seeing where this would go. A week after our first date, we became inseparable. Yes, it was genuinely romantic in all the ways Nora Ephron’s romantic films play out. Rich was ready to live again.

Friends were thrilled to see Rich dating since they knew how much he had struggled losing his beautiful mate. I was also excited by the newness he brought to a town I had spent over twenty years in and had so many brokenhearted memories from my marriage.

Friends that intimately understand the grief will most likely rally around both of you when they see your happiness. I met many of his friends on our dates, and it was always the same; genuine happiness that he had found someone, and I was lucky they liked me! Bonus!

2. A Ghost Amongst the Living: It’s Not That Scary!

The first thing you will notice when dating anyone who’s lost a spouse is that an entity resides not only in the home but in the heart and minds of everyone you meet.

Several of my friends assumed that being with a widower was much easier than being with a divorsé; no ex-wife to contend with or alimony squelching their bank account. That could make things seem more straightforward, but in reality, it’s the unseen that could make dating a widower insurmountable if you don’t have the right fortitude.

Photo by Lindy Baker on Unsplash

Embrace any family photos as a way to learn about the spouse, their relationship, and family dynamics. Think of it as a stroll through a museum of his heart and mind and how he ticks.

You will also learn a lot if you don’t take the reminiscing personally and engage in meaningful dialogue about his past life and experiences.

Regardless of the type of relationship you’re in, never compare yourself to someone else. Not only is this an unhealthy approach to your self-growth, but you would lose the chance to gain insights into his ability to create a healthy relationship and if he is ready to start a new one with you.

Here’s a tip I wasn’t expecting yet helped immensely. I felt very fortunate to “meet” Rich’s spouse during an impromptu reading by a psychic friend.

I had been dating Rich for about two months when I spoke with Mesina, a Medium I had met when researching a manuscript. During the reading, his wife popped in to say hello.

Whether or not you believe in connecting with those on the “other side,” it might well be worth your peace of mind knowing they are aware of your presence in their family’s lives.

Mesina described her looking angelic and peaceful. She validated her presence by a funny recount that happened in his home when I was struggling to learn where he kept things. His wife relayed my concern about how he liked his socks folded and other things I wanted to know about him and what he preferred. It was reassuring that she seemed delighted that he found someone she approved of for him and his family.

She also shared that he wasn’t meant to be alone. This was crucial in understanding Rich’s grief and how his dear friend saw the signs that he wasn’t doing well.

3. Accept What You Can’t Change — But Find A Tribe!

So here is the most brutal advice I can give you. You will always be Plan B.

Although Rich makes me feel special every day in every way, family members may have a difficult time accepting you in his life if they are in a different place in their grieving process.

They may accept that their father/grandfather should be happy, but there will be this unspoken rule that you’re never really going to be a part of their inner circle.

You will notice this during special events that pull the family together. Do not feel slighted when asked to stand out of a photo or not invited to an intimate affair. Understand that you represent what they can no longer have. A family photo would be proof of this, and that may be too hard for them to accept.

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

Emotional maturity isn’t related to their age but to an individual’s ability to both manage and understand their emotions. Emotional maturity helps us to cope with the difficult situations life throws at us.

Photo by Museums Victoria on Unsplash

Finding your tribe helps immensely with this dilemma. Luckily, I connected with several close friends of Rich’s who understood that all things change, and we must accept what life brings us.

They have been my support system during those difficult times and helped shore up my beliefs that I am a good person and that I do matter.

If you are struggling in your relationship with a widower, I hope you can see it is truly a unique situation and understand that it has challenges. Relationships can be beautiful when you understand the complexities and have some skills that can make them even more special.

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Deborah Holmén
Change Becomes You

Sharing my musing on the human experience, tapping into our greater purpose. Find me at The Good Men Project, A Parent is Born, Illumination, & Guide magazines.