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Bobbie Thomas opens up about experiencing her first breakup after her husband's death

TODAY's style editor writes: "Dating after loss can feel like two incomplete pieces of art, the artists deciding whether they can complement each other."

TODAY style editor Bobbie Thomas has been open about her grief after the loss of her husband, Michael, in December 2020. More than two years later, Bobbie is ready — or trying to be ready! — to get back onto the dating scene, although she says doing so brings up lots of complicated feelings. For “Bobbie’s Dating Diary,” on, she’s taking readers along as she figures out how the apps work, how to juggle dating with being a solo parent to her son, Miles, and how she can look toward the future without forgetting any of her past. 

I'll start this by saying: Sharing this has taken me some time. What I'm about to write is deeply personal and profoundly real to me, so I hope you'll bear with me as I open up.

When I committed to sharing my experiences with dating after the loss of my husband, Michael, in 2020, I made a promise to myself that I would be painfully honest about every facet of this journey. After all, why share if not to contribute an authentic voice to the world of dating, which is often trivialized with humor?

So, picking up where I left you last: You might recall I'd officially begun dating "the widower," and that back in late May, we were preparing for a weekend away together.

Catch up on the "Bobbie Dates" diary here.

I was anxious and excited leading up to the trip, and a little nervous about navigating the daily grind of an extended playdate while also trying to maintain a platonic demeanor. Although it might seem atypical to some, as two people who had lost spouses, we each completely considered it normal for our kids to sleep with us every night, which granted us some personal space as we stayed in separate rooms.

The weekend turned out to be 48 hours of relentless rain with two kids cooped up indoors. But amidst the marathon of dressing, meals, activities, snacks, teeth brushing, baths, and pajamas, we managed to find an hour after bedtime to squeeze in some TV, desperately trying not to succumb to sleep.

Our getaway also gave me a front row seat to witness his devotion to being a #girldad. From gently brushing her hair to meticulously packing her bag with the most adorable outfits (complete with a purse, headband, and all the essential accessories), it all truly melted my heart. And let’s not forget the healthy snacks and enough crafts to host a birthday party.

Dating as widowed parents can make five months feel like five years and only five dates all at once.

The Sunday drive back home was filled with mixed feelings. A wave of grief and moments of insecurity washed over me, but beneath it all, there was a sense of relief that we had survived. We did it! Most of all, I felt that our kids were, and still are, amazing considering the circumstances. These two resilient mini-humans possess the purest hearts that are thirsty for love, just like all of us.

Dating as widowed parents can make five months feel like both five years and only five dates all at once. It demands a level of maturity and almost administrative coordination just to find time together. And the time that is spent getting to know each other requires an even deeper level of communication and context, beyond what’s already required to sustain a relationship.

But that kind of transparency can leave little space for any enigmatic charm or the allure of mystery.

Nonetheless, the excitement and rush that comes with the potential of a new relationship is intoxicating. I forgot what it felt like to get dressed up (aka worry about matching underwear), be somewhere after dark (aka bedtime), and feel butterflies while getting to know someone new (aka I never thought I would date again after saying “I do”).

The first time around, falling for someone can feel like staring at a blank canvas, while you both hold paintbrushes eager to create something beautiful. In contrast, dating after loss can feel like two incomplete artworks trying to decide whether they can complement each other.

As summer unfolded, our routines were tossed aside and our respective social obligations with friends and family were added to the mix. We did our best to tackle it all, and were excited to now try a week-long stay with the kids. It was great to finally be together — but as the week wore on, so did the stress of managing two kids and our own respective responsibilities. Even though we were in the same place, it was still difficult to find one-on-one time.

After the trip, I was finally getting a chance to visit family and friends, while he was starting to juggle more than usual with work and other commitments. The initial excitement and frequent back and forth quietly shifted to a more transactional, casual dynamic, which, in its own way, was welcome. But deep down, I began to realize that casual is also the killer of communication.

Regardless, I wanted to let things I wasn’t focused on defining what “we” were, or where “we” were headed. I recognized the need for grace and flexibility as we both navigated our way to a new normal. That being said, when we did connect, I was hoping he might allow me to peer into the deeper layers of his being. Instead, it seemed he was more comfortable being supportive and thoughtful when I opened up. But with time, I think his reluctance to show me himself affected my ability to fully let my guard down —which influenced my personality with him.

There’s a curious "mirror effect" with trying to keep things "casual." On the one hand, it’s comforting to be held by another person, especially one who can understand the void of loss. It feels “right” to have someone at your side. But keeping it casual fills the immediate need without constructing anything new. My love for Michael and the hurt of losing him will always be a part of me, but I was ready, finally, to build something new.

After a few weeks of travel, opposite schedules, and feeling a bit disconnected, we finally planned a weekend together without the kids, and I was really looking forward to it.

I wish I could have paused and put aside my feelings from the prior weeks, to just be present in the moment that we were together. But I didn’t know how to hold back. Within an hour of my arrival, I dove right into a “talk” in an effort to feel closer. Instead, I could feel his emotional availability was out of reach.

The 2-hour drive home after making the decision to step back from one another was a deeply charged experience. While I was undeniably saddened by the turn of events, grief took over. Exhausted by the veneer of veiled and filtered communication that had settled between us, and disheartened by the complications that had crept in, I mourned the ease, and simplicity I had with my husband.

Why couldn’t we find a resolution together, even if it meant not being a couple anymore? After months of sharing meaningful aspects of our lives, it hurt that he couldn’t, or perhaps wouldn’t, “let me in.”

Or's simple, and he’s just not that into me.

Whether our waves of grief aren’t in sync or something else is meant to be, I’m thankful for the moments we shared.

I felt safe exploring my feelings, both physically and emotionally, with him. In many ways, his actions had earned my trust. I was drawn to him and willing to open up, even though there were no established rules and I was unsure about what the future held. It was comforting to know that we were finding our way forward together. I wasn’t in a rush, but I held high hopes that, regardless of our future as a couple, we, as widowed parents with children close in age, could at least lean on one another.

Whether our waves of grief aren’t in sync or something else is meant to be, I’m thankful for the moments we shared.

Despite each of our losses, we are both lucky to lead full lives. Yet, it’s one thing for our lives to be "full," and another to find depth and stillness amidst the busy schedule and the stream of friends and family with their own immediate lives.

Louise Eldrich put it well in "The Painted Drum," a novel released in 2005. “Life will break you. Nobody can protect you from that, and being alone won’t either, for solitude will also break you with its yearning. You have to love. You have to feel. It is the reason you are here on earth. You have to risk your heart. You are here to be swallowed up…”

After taking some time to reflect, I’ve realized that my feelings for the widower haven’t changed, and I cherish the sparks he created that brought happiness and hope into my life — something I’d sorely missed. Whether our waves of grief aren’t in sync or something else is meant to be, I’m thankful for the moments we shared. In some ways, I’m surprised, perhaps even unexpectedly excited. Not because we aren’t still dating, but because this connection helped me realize that I can feel...and that I’m ready to be open.

Now, I refuse to be guarded and will move forward with this knowledge.

The pain of losing someone you love is indescribable. Understanding this layer of his life, as well as my own, prevents me from passing judgment or harboring negative feelings toward him. We’re both doing our best to rebuild and let go of the future we had spent so many years imagining.

So now, I step forward, wiser and unapologetically open to feeling it all — because I can, I did, and I will.