The Most Iconic Seasons of The Bachelor

The Bachelor
John Fleenor via Getty Images

Season 28 of The Bachelor kicked off in January and is coming to a close on Monday, March 25. The season began with thirty-two women vying for the heart of 28-year-old tennis instructor Joey Graziadei, who originally appeared on Charity Lawson’s season of The Bachelorette.

Joey is now down to two women, Kelsey Anderson and Daisy Kent. We can’t wait to see who Joey gives his final rose to but until then, let’s brush up on our Bachelor history. This year marks 22 seasons that the franchise has been on the air. In the last two decades, there have been several memorable seasons but a select few really solidified the show’s place in pop culture.

Here are the most iconic seasons of The Bachelor.

Season 23: Colton Underwood

Photo by Lou Rocco/Disney General Entertainment Content via Getty Images

Colton Underwood’s season of The Bachelor in iconic more so because of everything that transpired after. The Football pro ended up with Cassie Randolph in the finale but the relationship turned sour after a year of dating. According to Us Weekly, the couple announced their split via Instagram in May 2020 in a since-deleted post.

In September 2020, the former couple were back in the news after Cassie filed a restraining order against her ex. E! News reported that a judge granted the temporary restraining order on September 14, 2020 ordering the former Bachelor to stay at least 100 yards away from Cassie. According to court documents obtained by the outlet, Colton “stalked” his ex, sent her “unsettling text messages,” and placed a tracking device on her car. She dropped the charges in November of that year.

Fans thought the couple’s tumultuous breakup was the last time the former Bachelor would make headlines for his personal life, but that was certainly not the case. In April 2021, Colton shocked fans when he came out as gay on Good Morning America.

“I’ve ran from myself for a long time. I’ve hated myself for a long time,” he said on the morning news show. “I’m gay. And I came to terms with that earlier this year and have been processing it. And the next step in all of this was sort of letting people know.”

Colton was the first gay Bachelor and we didn’t even know it. The aftermath of his Bachelor journey makes it one of the most memorable seasons to date.

Season 25: Matt James

Craig Sjodin via Getty Images

Matt James made history in 2021 as the first Black Bachelor and the third Black lead of the franchise, alongside former Bachelorettes Rachel Lindsay and Tayshia Adams. We can’t believe it took 25 seasons for there to be a Black Bachelor. He also broke a longstanding standard of former Bachelorette contestants becoming The Bachelor.

Matt’s season featured important conversations about race after news surfaced that his final pick, Rachael Kirkconnell, attended an Old South, Antebellum-themed party in college. The two split over the controversy but late reconnected. They are still going strong today.

Season 17: Sean Lowe

Photo by Noel Vasquez/Getty Images

Sean Lowe’s season is one of few love stories to come out of the show. Sean and his final pick Catherine Giudici have proven you can find a lasting relationship on reality TV. Since their time on the show, the two have tied the knot and welcomed three children. They are pretty much the poster couple for the franchise. Pretty much every lead since Sean has referenced him as “the right way” to be The Bachelor.

Season 13: Jason Mesnick

Paul Hebert/Disney General Entertainment Content via Getty Images

Jason Mesnick was the first Bachelor to pick the wrong girl but he wasn’t the last. The Washington native initially chose Melissa Rycroft but later broke off the engagement to pursue a relationship with Molly Malaney. The decision was controversial at the time but the couple has since proven their love is the real deal. They got married in 2010 and have since welcomed a daughter named Riley Anne. Molly is also a stepmom to Jason’s son, Ty, from a previous relationship. 

Season 24: Peter Weber

John Fleenor via Getty Images

Peter Weber’s season of The Bachelor is iconic because it was messy as h***. He was all over the place, the women were all over the place, it was perfection. During Fantasy Suite Week, Peter’s front-runner Madison Prewett decided to leave the show after discovering he had been intimate with another contestant. The conversation arose after Madison brought up her faith and her decision to save herself until marriage. Many fans thought Peter wouldn’t get engaged after Madison left but that was not the case. In the finale, he proposed to Hannah Ann Sluss, the recipient of his first impression rose. Shortly after filming wrapped, he dumped Hannah Ann and confessed he still had feelings for Madison. Oh boy.

He revealed on the After the Final Rose special that he and Madison were dating but it didn’t last long.

Peter’s season gave us so much reality TV chaos and we loved it. Between the break ups and his iconic mom Barb’s presence of the show, it was truly one to remember.

TELL US – WHAT IS YOUR FAVORITE SEASON OF THE BACHELOR?

X