’90 Day Fiance’ Star Darcey Silva’s Dating History: From Jesse Meester to Georgi Rusev

She wears her heart on her sleeve! Prior to meeting her ex-fiancé, Georgi Rusev, 90 Day Fiancé star Darcey Silva was in a few serious relationships that showed her exactly what she was looking for in a long-term partner. Take a look back at the TLC personality’s dating history and find out how she found love.

Was Darcey Silva Married Before? 

Before her rise to fame on reality TV, the star was married to now ex-husband Frank Bollok, the father of her two kids, daughters Aspen and Aniko Bollok.

“We just felt we grew apart and [were] searching for our soulmates,” Darcey told Heavy about why they split after eight years of marriage. “My relationship with my daughters’ father is good and respectful. I’m grateful for my daughters Aniko and Aspen and always will be. We are blessed to have them. They are my beautiful blessings and my angels! I love them with all my heart and soul and so does he.” 

Who Has Darcey Dated Since?

Darcey documented her long-distance relationship with Dutch boyfriend Jesse Meester on two seasons of 90 Day Fiancé: Before the 90 Days, detailing their tumultuous moments as well as the times they were head over heels. 

TLC viewers watched the couple’s messy breakup in a 2018 episode, which ultimately led her to move on with Tom Brooks, with whom she appeared on two more seasons of the spinoff. Darcey split from Tom on season 4 because they weren’t seeing eye to eye about how they envisioned a future together.  

After her breakup from Tom, Darcey connected online with a masseuse from Bulgaria named Georgi. They finally got to see each other in person in Miami during Super Bowl LIV in February 2020. By October of that year, Georgi got down on one knee to ask for her hand in marriage. 

How Many Times Did Georgi Propose to Darcey?

Just months before she announced their engagement, he proposed over the summer in June 2020. 

“I still feel newly engaged. I haven’t been able to really celebrate it yet with everybody. I want to be able to shout it to the world,” she told People. “It was definitely a total surprise for me. Georgi and I have a very deep connection, and I feel like in that moment I was not expecting it at all.”

He did a lot of preparation before the special moment, telling the publication, “It was really hard to find the ring, make calls, make the reservation for the boat, for dinner.”

However, the couple hit a rough patch shortly after and split briefly, calling off their engagement. After reconciling and going to couples therapy, their relationship was in a better place by the summer of 2021 — which is when Georgi re-proposed during a romantic beach proposal. Darcey, of course, said yes for the second time.

Did Darcey Use a Matchmaker?

During season 4 of Darcey & Stacey, fans watched the reality star go on a few dates with the help of a matchmaker named Michelle. However, she began to wonder if the matchmaker wasn’t a good fit when she was stood up by a man named Cicero.

“This whole situation makes me want to have a sit-down talk with Michelle and tell her how I’m feeling,” Darcey said in a confessional after Cicero didn’t show up to the date, noting that she also saw a photo of him on social media with another woman. “She vetted him for me, so it’s not just an issue between me and him, it’s an issue with her too. Like, what did I get myself involved with? I didn’t go into this dating journey with a matchmaker to get stood up.”

While talking to Michelle, the matchmaker warned Darcey that she might have been representing herself in an “inappropriate” manner on her past dates with Cicero.

Darcey admitted she felt “very disrespected” by Michelle’s comment and chose to stop working with her.

“I just feel like it’s not really working out. I’ve done a lot of the work that you’ve suggested, being open to dating older and different types that I’m not used to,” she said. “But this whole journey with matchmaking and dating has been totally disappointing. Maybe I just kinda need to do it on my own.”

Scroll through the gallery below to see the men Darcey has dated.