Brett, a 35-year-old with a career in information technology from Gretna, LA, shared in the clip he was previously engaged and the woman unfortunately cheated on him.
"So it didn't work. After my engagement fell through, I went on a lot of dates in a row -- just stacking them up," Brett noted in the clip.
"In the last few years, I've probably dated, I'm going to ballpark it, about 45 girls. It wasn't with the intention of them not working out; I want to find someone to spend the rest of my life with. I think I've been ready to be married for a long time."
Jamie therefore asked Brett how he knew he was ready to get married after having to get over the heartbreak of his failed engagement.
"That was a long time ago, and I have grown a lot since then," Brett replied.
"And I've actually had some more significant relationships since then as well, so that's all in the past."
Jamie also asked Brett why he thinks things didn't work out with one of the dozens of girls he had dated after breaking up with his former fiancee, especially since many people say "dating is a numbers game."
"I just think it's a lot of the 'I wasn't in the right place for them or they weren't in the right place for me' at any given time," Brett explained.
"Just finding someone you're compatible with in the first place is tough enough, and then making sure you're both in the same place in your lives where it's going to work, it's difficult."
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While viewers might view Brett's extensive dating history as a red flag, Married at First Sight expert Pastor Calvin Roberson apparently didn't see it that way when selecting Brett for the show's eleventh season.
"If you've dated a lot of people, I get it. People are trying to find The One, and with disposable relationships out here -- I mean, you're swiping left, you're swiping right [on dating apps] -- people get tired of that," Pastor Cal shared on Unfiltered.
Pastor Cal said he and fellow Married at First Sight experts Dr. Pepper Schwartz and Dr. Viviana Coles "have a few secret weapons" for getting insight into who a person really is during the casting process.
"What I want to know is, 'Do you have any strings that are attached?' It's okay that you've dated 45 people as long as there aren't 45 people out there waiting for you!" Pastor Cal said with a laugh.
While Brett has gone on a jaw-dropping number of dates, fellow MAFS participant Woody also gave off a smooth, player-like vibe during the Matchmaking Special. Even Woody's family and friends were shocked to hear that he wanted to wed.
"I like these guys, [Woody and Brett], because we want people who actually have a social life, who know what they want. The three of us picked them because we like them," Pastor Cal noted.
"We believe they are there, ready for the task."
However, Brett's wife Olivia, a 30-year-old nurse from Bossier City, LA, questioned Brett's motive for marrying a stranger in her Us Weekly blog after the premiere episode of Season 11 aired on Lifetime last week.
"It sounds like looks are everything to Brett, and the flirting ... eek! Some of the things Brett says are so shocking to me. He sounds like a playboy," Olivia wrote, adding that Brett's family and friends seemed taken aback Brett would even consider rushing to the altar.
Olivia added at the time, "It is not cool to hear about all of his past dates and canceling of dates. It makes me feel like he maybe isn't ready to settle down."
Olivia was also rubbed the wrong way when she watched Brett flirt with fellow MAFS groom Henry's female friend Kristin, who was invited to the men's bachelor party.
"I feel so bad for Kristin as Brett clearly made her feel so uncomfortable. Brett doesn't appear to be into the experiment based on the bachelor party," Olivia concluded in her blog post.
The other guys in the experiment even acknowledged during the premiere that Brett needs a woman who "can put up with a lot" and he seemed like the "consummate the marriage on the night of [the wedding] kind of guy."
"I'm a consummator," Brett admitted to the cameras.
Olivia was also pleased about her match and the fact he loves cats and enjoys watching a good movie at home. The pair learned they were pretty compatible during their first conversation after saying, "I do," and they both had hope they could have a long, fulfilling marriage.
In addition to Brett and Olivia, Married at First Sight's eleventh season also stars Woody and Amani, Henry and Christina, Karen and Miles, and Amelia and Bennett.