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Bobbie’s Dating Diary: Going on my first date since the death of my husband

Two years after the loss of my beloved husband, Michael, I’m dipping my toe into the world of modern dating … slowly.

TODAY style contributor 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. In a new series for, “Bobbie’s Dating Diary,” she’ll take 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. 

February 15, 2023

Do you ever feel ready?

After one of my regular segments for TODAY, I was in the dressing room, undressing (yes, the heels are swapped back for sneakers ASAP), when Sheinelle Jones came over with a warm hug. She told me about her recent interview with fellow widow, Julie Thomason (aka @SpilledMilkMamma), who had talked about sadness and joy coexisting. She’d shared with Sheinelle that she met someone new and found that “her heart expanded” to love more.

Can we make space for the past while also being open to the present? That’s the question I’ve been asking myself lately after a series of moments like that with Sheinelle and other friends. Two years after losing my husband, I find myself intimately acquainted with my grief, yet anxious about not wanting to put my life on hold until I feel “better” or “healed.” I wish those were attainable goals, but I know we carry memories and experiences from the past with us, which shape who we are. 

Can we make space for the past while also being open to the present?

Michael’s absence still leaves a gaping hole in my heart. But in addition to the place he occupies, my son, Miles, also monopolizes my heart. And that is what pushes me to move forward. I want Miles to be surrounded by positivity, and I want to be one of the people to inspire him. I want to show him how to look for the way forward and seek happiness. That starts with making space for my own joy and love.

I’m a people person, and I value relationships. I like sharing my life with people because it makes all the moments more special. So yes, I hope there is someone out there who is like-minded and who I can share my life with. It’s scary to think about all the challenges and checklists, but I’m learning to trust myself, and I’m willing to step out of my comfort zone.

But, of course, I’m also trying to brace for the unknown. I still have a lot of questions — which way do you swipe, again? — but I’m excited to start this journey. I didn’t expect to find myself in the dating world again, but I’m not going to let fear hold me back. Life is too short to wait for the perfect time or the perfect person. I’m ready to make space for the past, embrace the present and see where this journey takes me.

March 6

Here we go!

I’ve walked onto sets a thousand times, but I’ve never been as nervous to turn the page as I was when I arrived at the shoot to kick off a new series on TODAY with Hoda & Jenna called “Bobbie Dates!” Despite knowing that my longtime producer, Kelsey, was there to guide me through “a simple girlfriend chat” with my friend and Tinder CMO Melissa Hobley, I was bracing myself. Until now, my routine of Miles, family, friends and work had made it easy to avoid social invitations and hide from my own emotions.

Thankfully, Kelsey’s giant heart and smile beamed from behind the camera, while Melissa, who had stepped up to be my professional guide into the world of online dating, literally held my hand to download the digital dating scene and answer a million questions. My heart raced as she tapped “enable discovery,” followed by us both jumping when the first “like” appeared. Though my conflicting emotions were overwhelming, I knew that these “feels” were a nerve ending to connect with others. Direct message after message, comment after comment, conversation after conversation — so many stories of love and loss, heartache and hope. I realized that I’m not alone.

Later that night, I struggled. I finally got Miles to bed, stepped away from Netflix and attempted to get set up on two apps. My brain was exhausted, and I settled for “Bobbie, NY, Hello” in the “about me” section. Over the next 24 hours, I asked my best friend to help with my profile, swiped in the wrong direction, tried to come up with the perfect opening line and nervously waited for responses. 

March 21

Getting to know the apps

Over the past two weeks, I’ve done my best to learn the ropes. Here are some cliff notes: First up, Tinder. It was free, and in less than two minutes, I was in the mix. Gulp. The setup process was surprisingly short, and I was relieved that I didn’t have to share too much personal information. If you’ve ever felt like there’s no one out there, this one’s for you. I was surprised by how many people were on the app. Before I adjusted the filters, I was seeing potential matches ranging from 21 to 76 years old (Vinny, I’m flattered 😉). And cool sidenote: You can set your location to anywhere in the world. My experience was exciting, but a bit overwhelming since it felt like going from 0 to 60 in minutes.

I also downloaded Hinge, another free app. I was quickly sold by their motto that it’s “designed to be deleted.” I loved the prompts that helped me to fill out my profile, such as “First round is on me if ... ” (it’s before 5 p.m.!) and “We are the same type of weird if ... ” (you would rather order in versus face the crowd at a trendy spot). The answers give you a glimpse of someone’s personality and make for a great conversation starter if you match. Additionally, I have to say that there’s nothing quite like the feeling of stumbling upon an audio snippet on someone’s profile and being completely taken aback by an unexpectedly sexy British accent (cue my immediate swooning for “the creative type” who’s “only grumpy when it rains”). It’s moments like these that make the online dating experience all the more exciting and memorable.

Last but not least, The League is an app that Jill Martin, my TODAY colleague, used to meet her husband. Her story inspired me, and I loved that the app was founded by a woman. It’s designed for busy professionals, and I liked that it connects to your LinkedIn profile so you can avoid seeing coworkers. My friend Melissa liked that it takes longer to set up a profile, which hopefully weeds out guys who aren’t serious. However, you have to be approved to join the app, it’s not free and it’s also not available in every city. 

March 28

My first date

I’ve secretly started to love Mondays over the past two years because they bring structure with Miles in school and me having work to tackle. But on a Monday in late March, I had something else on the schedule: My first official (blind) date was scheduled for 7 p.m. That’s right: After all my efforts figuring out the dating apps, my first date was … not from the apps. My friend set me up. I was distracted with anxious thoughts all day, which led to me running behind with meetings and tasks. I couldn’t stop thinking about how and if I’d approach this with Miles — but that’s a diary entry I’ll save for another day.

It was lovely to have an adult conversation and a break from routine, but I couldn’t help feeling disconnected.

When I finally got home, I had only 15 minutes to get ready. I rushed out the door and arrived awkwardly at the restaurant. Was he there? Unsure of what he looked like, I stood there staring, then looked at a text that described where he was sitting. He was kind and exactly what I had asked for. Polite to the staff, warm and easy to talk to. It was lovely to have an adult conversation and a break from routine, but I couldn’t help feeling disconnected. As I sat across from him and he shared things about his life, I heard what he was saying but the energy was louder. He seemed so ready to plan a wedding, start a family — that first chapter of adult life, one that feels long ago for me. 

March 29

The morning after

Despite nothing being wrong, today I woke up feeling overwhelmingly sad. I’m missing Michael more than ever, and I’m feeling angry that he doesn’t get to be part of my second chapter. I’m also thinking about someone — not the date from last night. 

A day ago I had a platonic meetup, initiated by friends of my in-laws, with another parent who had also lost his spouse. Unexpected feelings are coming up. I can't stop circling back and thinking about the ease and shorthand we shared. We checked our baggage at the onset, and could uniquely understand the context of each other’s current lives. Although the focus was on introducing the kids, there was an instant comfort with someone I had just met minutes before. It was something I hadn’t been able to do: focus on the now, and not what had happened. But it wasn’t a date … was it? I can’t stop thinking about the connection, and now I’m secretly hoping for a one-on-one coffee with him — but I’m not sure how or if that would ever happen. 

Now that Miles is snoring, I keep my promise to my producer (“Just 5 minutes a day!”) and open the apps. Cycling photo, hiking photo, “active, fit and adventurous” bio lines from men scroll by.

Stay tuned to Bobbie’s Dating Diary to find out if she gets any responses on the apps — and if her relationship with her new friend becomes something more romantic.