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Bobbie's Dating Diary: I never thought I'd kiss another man again — and then, the butterflies came

I’m trying to make sense of this newness in my life, but it’s equal parts unsettling — and exciting.
TODAY Illustration

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. 

April 1, 2023

A confession

I stepped into this world of online dating unsure if I was really ready — but I had no idea how many feelings were sitting just below the surface. Something about saying “okay, yes” out loud has allowed me to acknowledge how much I miss feeling close to someone: the hello hug or kiss goodbye, their hand on my back, the tucking of my hair behind my ear.

It spirals into so much self doubt at times. A part of me wonders: ‘How could I ever love someone so deeply again?’ I also doubt how someone could ever love me — all of me, with the baggage, responsibilities, and permanent mark on my heart left by Michael. And I also wonder how I'll ever get the guts to let someone new see the ‘now’ me, with my older not-so-tight bod, post-baby tummy, scars and all.

Michael had the preview but had also evolved alongside me over the years. Without context, I feel less confident baring all. Someone new sounds exhilarating, but a supportive, caring, loyal and lasting partnership makes every inch of you feel loved unconditionally.

April 5

Houston, we have a message!

Wow, getting a conversation off the ground is so much tougher than I had expected. I was excited to see a few messages pop up in my app, but I was nervous to read them, let alone respond.


“Hi Bobbie! Nice to meet you here.”

And now the ball is now in my court. For some reason, I couldn’t think of anything beyond: “Hi, you too.” What am I doing? Note to self: ice breakers needed. And I’m embarrassed, but I have to be honest here: I dropped the ball on many of the app messages because I just couldn’t think of anything — nothing, nothing at all! — to say. There were a few OK chats, thanks to info shared in the profiles, but I've found it’s really hard to know if you like someone when you can’t experience someone’s in-person vibe. Thinking back to my past, I've always been most attracted to someone’s actions: how he treated others, made me feel, and carried himself.

I was beginning to get discouraged by the online chats, and then the text I had been hoping for flashed across my screen. Remember the fellow widowed parent I had met up with for coffee? He finally reached out. I’ve been telling myself that if he asks to get the kids together again, then I’d know where his interest was. Sure enough, he wrote: “Let’s do something!” … with the kids. My heart sighed.

But when I looked back at my phone 30 minutes later, I had missed a second text: “I would also love to go out without the kiddos.” Eek! I’m not sure I remember the last time I felt this way. There it was: that sudden spark that zaps your stomach with butterflies.

24 hours later, I was sitting across from him, still slightly unsure if this was a date or a "let’s trade widowed parenting tragedies" dinner. We cautiously poked around with a few questions, but the anxiety was quickly replaced with knowing nods and mutual understanding of topics I usually dread explaining to someone. It was nice to just... be. To be both present and understood...and yes, to be kissed! But best of all, it was nice to receive this text right after he left: “Tonight was amazing. Thank you for being so thoughtful and funny and loving and interesting and beautiful.”


April 8

Reality Check 

I know that I am “a lot” in some ways. And while that’s okay in certain aspects of my life, in others, I can’t help but question if I’m too much for someone else to handle. Will my complexities, my vulnerabilities, and my insecurities be too overwhelming for someone else? Being a widow is not just a part of my story, but a stark reality that I have to face every day. Caring for my son (and his big feelings) alone, managing a household and life without a partner, all while navigating an atypical career can be overwhelming at times. (Not to mention sharing my dating diary with the world!) I also need to balance keeping up with family and friends, both mine and Michael’s, while doing my best to squeeze in self-care.

I’m trying to make sense of this newness in my life, but it’s unsettling. It’s like navigating uncharted waters with the constraints of a life built. I remember when getting to know someone new used to be easy, when I was more flexible and less tired. Oh, how I miss the days when I was in my 30s, full of brightness and optimism. 

April 11

All or Nothing

“I thought it was all or nothing? Wouldn’t that leave like...a stripe?!” I’m floored, gutted, and crying laughing at my 20-year-old assistant’s reaction. I don’t think there is any better confirmation that so much has changed: An appointment on my calendar read “bikini” (shorthand for bikini wax), which she understood to be something different.

With dating now a daily topic in the office, our conversation shifted to what she and her friends considered as the going standard for "down-there" care. It was a hysterically confusing chat, as it took me a minute to realize she genuinely did not get what I meant by "options" (ie. strip, triangle, brazilian, lol).

“I’m like, trying to picture it?” She says, confounded. Then she Googles and responds, wide-eyed: “This can’t be real.” I only wish Hoda and Jenna had been in my office. You might think this is a taboo topic for morning television, but no... Hoda and Kathie Lee Gifford’s “waxing poetic” chat from 2013 is still seared in my memory.

A conversation I never thought I'd be having, but here we are! Until next time...

Stay tuned to Bobbie’s Dating Diary to find out: Did she go all or nothing?! Will Bobbie continue dating her new mystery man? And... what's happening on those apps?