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Bobbie’s Dating Diary: A message to anyone who wonders why I’m doing this

You’ve all been asking — here’s my response. Plus, an update about how it’s going with the widower.
In her latest entry, Bobbie Thomas addresses some of the fan questions she's gotten about her dating journey.
In her latest entry, Bobbie Thomas addresses some of the fan questions she's gotten about her dating journey.TODAY Illustration / Nathan Congleton / NBC / Getty Images

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 TODAY.com, “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. 

May 11, 2023

Lots to unpack … 

It’s been a few weeks since my last post. I took a break from writing to just experience dating. I felt the need to “feel” before thinking too much about it.

First and foremost, I wanted to share this diary with the hope that it provides a sense of comfort and reassurance to those who may feel alone in their experiences and emotions. The power of community and connection can be transformative, offering a universal sense of understanding and healing. Reading messages from so many who have been inspired to download a dating app, say yes to someone new, and/or take steps to open the door to a new chapter has been uplifting. I’ve also read some of the comments questioning why I would share something private so publicly. While the nature of social media has opened my decision up for debate, I appreciate that most of the comments, both positive and negative, come from a place of concern. Some asked if I was being pressured, others worried that potential suitors would shy away, or how my transparency may affect my son, Miles, down the line. 

If someone chooses to stay away from me because I express my emotions openly, then they are not the right match for me.

I replied when possible to comments I came across on social media, and I want to reassure others that after spending 17 years in Studio 1A, I am deeply grateful for the love and unwavering support from my TODAY family behind the scenes. If someone chooses to stay away from me because I express my emotions openly (with discretion), then they are not the right match for me. Even when Michael disagreed with me about announcing my pregnancy at 5 weeks, he was my biggest cheerleader and sat beside me on live national television to share the news. That is the bar he has set, and I firmly believe someone else can step up. 

As for Miles, he is a consideration in every decision (big and small) I make, every day. I wholeheartedly believe that it is in his best interest that I am honest, authentic and vulnerable, and that I seek joy and look to the future with hope and excitement. I do not want him to ever feel ashamed about his feelings, good or bad, and I hope he feels confident in being himself and sharing who he is unapologetically. This is the only way to have meaningful relationships of any kind, and what else truly matters more in life than love and connection? There is nothing I feel more strongly about. With profound sincerity, I hope that by adding my voice and story to the fabric woven around widowhood, and simply being someone looking forward to loving again after 45, I can help break down stereotypes, dispel shame, and create a welcoming and inclusive environment that combats loneliness and fosters a sense of belonging.

Transitioning now to a recent realization, it’s been 2 years since Michael’s passing, yet my sense of time still feels distorted. Some days it feels like he was here only yesterday, while on others, it feels like our love belonged to another lifetime. Despite this, the thin membrane separating my conscious thoughts and focus remains fragile, and can be torn apart by a simple poke, unleashing the most excruciating and unbearable pain that leaves me short of breath and wondering if I’ll ever be OK again.

That being said, 2 years on, I am a completely different person. It felt like another loss to acknowledge that the version of “me” that stood by Michael’s bedside now seems foreign. Initially, the realization was scary. However, my body moved forward, and my heart and mind were dragged along somehow. What I was forced to accept, bear and carry with me has shaped how I think and feel today. I couldn’t have fathomed surviving 2 years, let alone embracing the emotional transformation that was to come.

I share this because dating can force you to confront yourself. Questions like “tell me about yourself,” “what do you enjoy,” and “what do you want” can be challenging, especially when you’ve spent some time feeling numb, only to discover that you feel vastly different now. 

It’s been fun to message with some matches online and go out with friends for drinks or dinner, with some chance encounters leading to meetings with new people. However, I’ve found myself struggling to answer simple questions and feeling unsure about how to open up. It’s as if I don’t know myself anymore, which is disconcerting because I enjoy being social and open.

I’ve found myself struggling to answer simple questions and feeling unsure about how to open up. It’s as if I don’t know myself anymore, which is disconcerting because I enjoy being social and open.

Meanwhile, I’ve been seeing the fellow widowed parent I mentioned previously, and we seem to have skipped past the usual introductory questions and clicked naturally. At first, I thought it was because we shared similar losses, but then I realized how much I’ve changed. My priorities have shifted and my walls are down now. I’m vulnerable in a way that I wasn’t — that I couldn’t have been — before. It’s scary to have feelings for someone new. Starting fresh is both exhilarating and terrifying, triggering all kinds of emotions and insecurities that make me question myself.

There have been some butterflies, both good and bad, and some late-night phone calls where only a best friend would indulge my overanalyzing of a text message. It’s exciting to feel these things again, but also daunting to experience the nerves that come with a new connection after so long. It’s funny how just when I thought I had wrapped my head around dating, my heart throws me for a loop with this next "in-between phase," the delicate area between first dates and an official relationship. 

It’s as if I’m a teenager at times, with my emotions bouncing between “yes, YOLO” and “whoa, wait, no,” questioning if feelings are mutual and worrying about getting hurt. How do you navigate the unspoken rules and maintain a certain level of distance while also trying to develop a deeper connection? 

The widower and I just put a weekend overnight trip with our kids on the calendar. I’m really excited about the idea of getting some real time together, as squeezing in time during the week is a logistical blur for two solo parents without a baton, but gulp. Wish me luck.

Stay tuned to "Bobbie's Dating Diary" to find out how Bobbie's weekend trip with her new crush goes.