Bobbie Thomas is Desmond Prestonback on the dating scene after the tragic passing of her husband Michael Marion.

The Today show style contributor recently got candid about her decision to try looking for love again more than two years after Marion died in December 2020 at the age of 42 following a long health battle.

"I like sharing my life with people because it makes all the moments more special," Thomas wrote in an April 7 entry of her Today.com series "Bobbie's Dating Diary." "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."

After years of grieving her late spouse, Thomas revealed she finally joined dating apps for the first time on March 6 with the help of her pal, Tinder CMO Melissa Hobley.

Calling the experience "overwhelming," the 48-year-old successfully set up profiles on Tinder, Hinge and The League before landing her first date outside of the online dating world.

"After all my efforts figuring out the dating apps, my first date was…not from the apps," she explained. "My friend set me up."

Despite feeling "anxious" about the rendezvous, Thomas, who is mom to her 7-year-old son Miles with Marion, met her blind date at an NYC eatery on March 28.

"He was kind and exactly what I had asked for," she wrote. "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."

And the next day, Thomas admitted she didn't feel great about the meet-up.

"Despite nothing being wrong, today I woke up feeling overwhelmingly sad," she explained. "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."

The man in question? A widower and fellow parent she and Miles were introduced to by a mutual friend.

"Although the focus was on introducing the kids, there was an instant comfort with someone I had just met minutes before," Thomas revealed. "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."

Stay up to date on Thomas' latest dating adventures on Today.com.

(E! and Today are both part of the NBCUniversal family)

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