Barbara Corcoran, mentor on Shark Tank, recently shared a moment from her past on Instagram. On March 20, 2025, on National Proposal Day, she posted a clip from her March 2023 interview on the Chicks in the Office podcast, where she spoke about her approach to relationships.
During the conversation, Barbara said that she had proposed to everyone she "ever married.” When asked if that was really the case, she affirmed.
“Really. Oh yeah. I wasn't wasting time. Proposed to my first husband, my second husband and my first boyfriend,” she replied.
The 2023 podcast episode covered many parts of Barbara’s life, including her early days in New York and her experience as an investor on Shark Tank. She explained her thoughts on taking the lead in relationships. In her words, waiting wasn’t part of the plan. She explained that once she knew someone was right for her, she didn’t hesitate to ask the question herself.
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Shark Tank mentor Barbara Corcoran explains her approach to marriage
Shark Tank star Barbara detailed how her proposals usually happened about a month into dating.
“You know what happens— you know who you don’t like more. You know this ain’t gonna work. So when you find somebody good, I would look at them and think, would this make a good husband?” she shared.
Instead of waiting for her partners to make the first move, Barbara said she was direct with her intentions.
“I just corner him. I said, ‘What’s your intention?’” she said.
She laughed while recalling how she gave them a couple of days to think and then followed up asking what have they decided about her proposal.
Reflections on love, loss, and moving forward
Barbara also reflected on her first serious relationship, sharing how it affected her when it ended. Recalling the breakup with her long-time boyfriend, who left her for her secretary.
“It was debilitating. I could hardly walk,” she said.
She described how she was initially devastated, but over time, she found a way to view the experience differently.
“She was prettier than me… she had long blonde hair and she’s five years younger than me. I didn’t blame him,” Barbara admitted.
Despite the effect the break up had, she discussed how she eventually regained control. Speaking about her second husband, she shared, that they have been married for 33 years but it "feels like 150," and she added that Bill wasn't "going anywhere."
Building confidence through trying, not waiting
In the same podcast, Barbara Corcoran spoke about confidence and how it shaped her choices over time. She shared that it didn’t come naturally but was something she built by continuously putting herself out there.
“I looked confident to everyone... I knew I didn’t know what I was doing. I was just inventing as I went,” she said.
Shark Tank mentor Barbara Corcoran explained that her focus was not on outcomes but on consistent effort. She believed that her strength lay in trying again and again, even after setbacks. Instead of seeking perfection, she chose persistence. She also said that becoming comfortable with rejection was essential.
In her view, people who continued to try after failure eventually created space for success. This mindset, she noted, influenced how she navigated both business and personal relationships, including her decision to take the lead in proposals.
Catch the latest episodes of Shark Tank currently available to stream on ABC.
