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Navigating Grief and New Relationships: It’s Complicated

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The challenge of navigating grief and new relationships is the reason that I always want to select the “it’s complicated” option as my relationship status. It’s hard to tell a date about your divorce or the death of a partner. I’ve had to learn to do both things.

Not ideal, I know. But it does mean that I know a thing or two about dating after loss. This particular story starts where nobody wants to be. Ever. This tale begins at the dentist:

Grief and new relationships: It’s even hard to tell the dentist!

I went back to my childhood dentist the other day. We hadn’t seen each other since I left town for college some 15 years ago, so we had some catching up to do. As he maneuvered a long inspection mirror into the back of my mouth, he asked:

It is amazing to me that dentists can somehow understand the strangled gibberish that escapes a mouthful of instruments.

We politely talked about sustainable alternatives for traditional toothpaste and dental floss for a while before he tentatively asked about my last name.

Of course, I thought, here I am mumbling around his gloved hands about writing as a solo traveler and single woman, while he is wondering about my maiden name — or lack thereof. He knew me by an entirely different name.

My marriage lasted just five years and ended in 2008

“I’m divorced,” I explained, quickly adding the part that makes people feel better when they stumble down this line of questioning. “More than 10 years ago now.”

Conveniently, we reached a part of the exam that requires silence on the part of the patient, so I closed my eyes against the glare of the overhead lighting and thought about the part that’s even harder to say.

How do I bring up the reason that I am a solo traveler? How do I bring up the fact that my fiancé died?

I can tell you this much, I wasn’t about to bring it up while my dentist had stainless-steel instruments in my mouth.

Not a good time for a deep chat

Reactions to a grieving person are all over the map

Because I have seen all sorts of reactions as I’ve navigated this tricky bit of background information.

The eyes tend to widen slightly and, in most cases, there is a spontaneous show of sympathy. Sometimes that is as simple as a pat on the hand with watery eyes, other times arms are flung around me in a sudden hug. Often an “oh, I’m so sorry” is followed by an effort to exit the conversation as quickly as possible.

I’m not criticizing these responses. Honestly, there is no perfect way to react to a grieving person. I have, however, learned that there is one response that gets me to stop holding my breath when I broach this subject.

That response goes something like this:

The best way to tell a new person about your grief

See, the subject of Jeff’s death is not hard for me to talk about anymore. It’s the opposite. I like to remember Jeff and the short but transformative relationship that I had with him before esophageal cancer ended his life at the age of 40. He was, in fact, a great guy.

My late partner. My immortal love.
Jeff just two months before he was diagnosed with cancer

It took me 18 months to learn the reaction that puts me most at ease. But I’m still working through how best to bring up Jeff and keep others at ease. Calling this a tricky subject is an understatement.

I mean, if it’s hard to bring it up with the dentist, imagine how hard it is to bring it up with a date!

I do have hope, though. I figure that just as I’ve managed to find a response that puts people at ease when they stumble on that chapter of my life that includes divorce, I’ll manage to find a way to work in the chapter that includes death.

So far the best way that I’ve found to navigate grief and new relationships is to say something like:

Navigating grief and new relationships takes trial and error

It will take trial and error and, I’m sure, a few terrible dates filled with trial and error. (Which, at least, will result in good writing material!)

As for my dentist, when I explained that I have been traveling and writing because I quit my nine-to-five after my fiancé died, he gave the obligatory “oh, I’m so sorry,” and left the room as fast as possible.

Which was just fine with me. Nobody wants to spend more time than necessary with the dentist.

Do you have a good way to navigate grief and new relationships? Tell me in the comments below!

About the Author

Hi! I’m Jen!

I’m a freelance writer and travel blogger who quit my nine-to-five after my fiancé, Jeff, died of cancer at the age of 40. When he died, I realized that life is just too short to delay our dreams. Since my dream was to travel and write, I now travel and write full-time. Today I wear hiking boots instead of heels and collect experiences instead of things.

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Resources for Grieving


Grief Works: An app to guide you through your grief


Hot Young Widows Club: Stories of love & loss on Instagram; also a book


Modern Loss: Essays & resources to navigate life after death


Good Mourning Podcast: Authentic conversations about loss


Soaring Spirits: Peer-based support programs for widowed men & women


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