Barbara Corcoran, a renowned mentor on the popular show Shark Tank, recently took to Instagram to reminisce about her past experiences with love and relationships. On March 20, 2025, coinciding with National Proposal Day, she shared an excerpt from her March 2023 appearance on the Chicks in the Office podcast, where she candidly discussed her unconventional approach to proposals.
Breaking Tradition: Barbara Corcoran’s Unique Proposal Strategy
During her podcast interview, Barbara confirmed a bold claim: she had proposed to every significant partner she had married. When challenged about this assertion, she maintained her stance with humor and conviction.
“Really. Oh yeah. I wasn’t wasting time. Proposed to my first husband, my second husband and my first boyfriend,” she replied.
Barbara elaborated on her experiences, explaining that her proposals typically occurred just a month into dating. She conveyed that her method was straightforward; she never believed in waiting for someone else to take initiative.
“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.
She took a bold approach, often addressing her partners directly about their intentions.
“I just corner him. I said, ‘What’s your intention?'” she said, laughing at the memory.
She humorously recounted how she would give her partners a few days to ponder her proposal and then would follow up with them for their decision.
Lessons from Love: Navigating Heartbreak and Recovery
In her podcast, Barbara also reflected on her personal journey through love and loss, particularly regarding her first serious relationship. Sharing the story of her breakup with a long-term boyfriend who left her for her secretary, she painted a vivid picture of the heartache she endured.
“It was debilitating. I could hardly walk,” she reflected.
As she processed this painful experience, Barbara gradually shifted her perspective, acknowledging the qualities of her ex-boyfriend’s new partner.
“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 initial sorrow, she revealed how she eventually reclaimed her strength. Regarding her second marriage, she quipped that she and her husband Bill have been married for 33 years, but it “feels like 150,”emphasizing Bill’s unwavering presence in her life.
Empowerment Through Resilience: Building Confidence
Barbara Corcoran also addressed the topic of confidence in her interview, explaining how it was not something she was born with, but rather a characteristic developed through action and perseverance.
“I looked confident to everyone… I knew I didn’t know what I was doing. I was just inventing as I went,” she explained.
Her philosophy centers on the idea that success hinges not solely on outcomes but on the dedication to continually put oneself out there. She believes that the strength to maintain effort in the face of adversity is key to creating opportunities for success, whether in business or personal relationships.
Barbara emphasized that embracing rejection is a vital part of this journey. Those who continually strive after setbacks inevitably pave the way for future accomplishments. This mindset has been instrumental in shaping her approach to proposals, reinforcing her belief in the importance of taking the lead.
For those interested in following Barbara’s journey and her insights into entrepreneurship and relationships, catch the latest episodes of Shark Tank, which are available for streaming on ABC.