The Season 5 Bachelorette began her answer by stating that their relationship "has been really unconventional," much of which could do with the fact that Justin is 10 years younger than she is.
Jillian explained that when she met Justin, she had "given up."
"I started my find my success as a human. I’m starting to enjoy my alone time," she said on the podcast. "I had guys in every area code, and I was proud of it. I’m not ashamed of that time in my life at all, because I was confident in myself. I had a boyfriend in Holland, in Hollywood, one here [in Canada]. I was confident in myself. I had really strong boundaries."
At this point, Jillian was 32 and she told herself she would look into artificial insemination when she turned 36.
She recalled thinking, "I’m going to have babies on my own, and whenever a relationship happens for me, it happens for me."
One night, Jillian was in line for a bar when she met her future fiancé.
She explained, "I was like, 'Oh, he is cute! He’s 10 years younger than me.' I was like a black widow and this is my next victim. We started chitchatting and I could tell he was raised well," meaning she could tell he had a "nice heart."
The Jilly Box owner continued, "Normally what I would do with a nice guy like that is I would sabotage it before the first date. I would be like, 'He’s too nice.' I was going for the bad guy because I knew how to handle them. I already set myself up for failure and I didn’t want to get myself heartbroken again. I was self-sabotaging myself the whole time in terms of a relationship. That’s all I knew."
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She said that before "The Bachelorette" and her relationship with Ed Swiderski, the men she went out with were "not good guys."
Jillian told Becca and Rachel, "When I met Justin, I found out he was 23, and I was 32. I was like, 'What are we gonna do? I want to have babies and you’re not ready to have babies at 23. This is a disaster.' We dated for a good four years. I was turning 36 and we talked about engagement a lot. We had a really rough relationship because of our age difference and also the difference in our careers and where we were."
Justin was a pro snowboarder and quit, which, according to Jillian, Justin "felt like he was the famous one with the crazy career." Then he met the former Bachelorette and it wasn’t always the case.
She admitted, "We really struggled in our relationship and I think that’s why we never got engaged, because we were both like, 'I don’t know if we’re going to get through this.' One day I said to him, 'Honestly, I know you haven’t proposed yet, but do you think I’m going to be the one you’re going to have babies with?' He was like, 'Yes.' I said, 'Because my clock is ticking, which means your clock is ticking.'"
Justin and Jillian said they'd "start trying" to have kids when she turned 36. A month before her birthday, she found out she was pregnant with their first child, Leo. Five months after Leo was born, Justin proposed (the first time) on Christmas morning.
To hear the rest of Jillian's conversation with Becca and Rachel, be sure to listen to the full "Bachelor Happy Hour" episode now!
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