Despite a happy engagement in the finale of The Bachelorette Season 18, Michelle Young and fiancé Nayte Olukoya have called it quits after only about six months. Young and Olukoya both shared the news over Instagram, explaining that while they have love for each other, they’re going their separate ways.
Which begs the question: Did Michelle get to keep the ring?
According to Bachelor tradition, no. Several Bachelor/Bachelorette contestants have spoken in the past about the details of the contract they sign before joining the show, sharing that if couples break up within two years of the finale, they must return their ring. However, if they make it past two years, the bling is theirs to keep.
So, which couples have gotten to keep their rings? There are plenty of contestants and winners who haven’t stayed together for two years — but what about the ones who stuck it out just long enough to hang on that jewelry?
Without further ado, here are five couples from The Bachelor franchise who made it past the two year mark and got to keep their rings, despite not truly finding their happily ever after — and ten who didn’t even come close.
The Engaged Couples Who Could Keep The Ring
Byron And Mary - The Bachelor Season 6 (5 Years)
This couple from the early days of The Bachelor stayed together for five years. It wasn’t a perfect happy ending though — Mary Delgado was arrested for assaulting Byron Velvick in 2007.
Allie And Roberto - The Bachelorette Season 6 (18 Months)
This is a controversial one. Allie Fedotowsky and Roberto Martinez didn’t make it past the two year mark — but when producers came to retrieve the ring from Fedotowsky, she refused to give it back.
Claiming 18 months was long enough to keep the ring, she convinced the Bachelor team to let her keep it anyway. I highly doubt that would ever happen today, but given that the show was in its early years, the producers made an exception.
Ashley And J.P. - The Bachelorette Season 7 (8 Years)
Ashley Hebert and J.P. Rosenbaum were once considered one of the most successful Bachelor franchise couples of all time. They were even married on TV as part of a Bachelor TV special. However, the pair announced their divorce in October of 2020. They still co-parent their two children together.
Eight years is still quite an impressive relationship though, especially by Bachelor standards. They pass the ring clause with flying colors.
Kaitlyn And Shawn - The Bachelorette Season 11 (3 Years)
Kaitlyn Bristowe is a seasoned veteran of the Bachelor franchise—she’s been a contestant on The Bachelor and starred on The Bachelorette, and even stepped up for some hosting duties after Chris Harrison’s removal from the role.
Unfortunately for Bristowe, her Bachelorette journey didn’t end in marriage. She and her Season 11 winner, Shawn Booth, split in 2018, with Bristowe citing “important fundamental values” as one of the reasons they couldn’t quite see eye-to-eye.
Carly And Evan - Bachelor In Paradise Season 3 (4 years)
Carly Waddell and Evan Bass got engaged on Bachelor in Paradise and got married soon after. They even have two children together!
Despite being one of Bachelor Nation’s favorite couples, Carly and Evan split after three years of marriage. They tried to make it work, even attending couples therapy, but ultimately made their separation public in 2020. We’ll likely never know the full story behind their downfall, but we do know they lasted long enough to beat that sneaky ring clause.
The Engaged Couples Who Couldn't Keep The Ring
Jesse And Jessica - The Bachelor Season 5 (1 Month)
Most people know that current Bachelor host Jesse Palmer was actually the Bachelor himself back in the day. But did you know that his relationship with winner Jessica Bowlin only lasted one month?
There was no ring involved, since Jesse didn’t propose during his finale, but it’s not like they would have gotten to keep it anyway.
Juan Pablo And Nikki - The Bachelor Season 18 (7 Months)
With a reputation as one of the worst bachelors of all time, it’s no surprise that Bachelor’s Season 18 lead, Juan Pablo Galavis, didn’t really find his true love on the show. While he chose to give his final rose to Nikki Ferrell, the two split after only seven months.
Not even VH1’s Couples Therapy could save this doomed relationship, so the pair went their separate ways.
Chris And Whitney - The Bachelor Season 19 (6 Months)
While the exact timeline of this relationship is unknown, Chris Soules and Whitney Bischoff definitely didn’t make it down the aisle. After an alleged six-month engagement, the couple split.
It’s probably for the best, as Chris Soules was arrested in 2017 for fleeing the scene of a car crash where one person was left dead.
Ben And Lauren - The Bachelor Season 20 (1 Year, 2 Months)
Ben Higgins and Lauren Bushnell definitely put a dent in that 2-year agreement, but made the choice to split after just over a year of engagement. To answer the question posed in the couple’s Freeform reality show, Ben and Lauren: Happily Ever After?: No. Unfortunately, it was not happily ever after. No ring for you, Lauren.
According to Ben, the relationship was over long before the split became official. Maybe having a camera crew document your every move isn’t the best way to create a loving relationship, after all.
Nick And Vanessa - The Bachelor Season 21 (5 Months)
Like Kaitlyn Bristowe, Nick Viall has been around the Bachelor block a few times. He’s been a contestant on The Bachelorette twice, and appeared on Bachelor in Paradise before returning as the lead of The Bachelor Season 21.
Nick’s experience in the Bachelor game didn’t help his relationship with Vanessa Grimaldi, and the two ended their engagement less than six months after the finale. Not even Allie Fedotowsky could convince producers to let a woman keep a ring from a five-month engagement.
Colton And Cassie - The Bachelor Season 23 (1 Year, 2 Months)
This one’s no surprise: Bachelor Colton Underwood didn’t find the woman of his dreams on The Bachelor. While his relationship with winner Cassie Randolph lasted over a year, Colton came out as gay in April of 2021, during an interview with Good Morning America. His coming out was documented in the Netflix reality series, Coming Out Colton.
Good for Colton! No one from the couple gets to keep that ring, though.
Hannah B. And Jed - The Bachelorette Season 15 (5 Weeks)
The Bachelorette princess Hannah Brown chose Jed Wyatt as the winner of her Season 15. The dreamy romance came to an end, however, when rumors began to surface that Wyatt had only come on the show to boost his music career and also had a girlfriend at home waiting for him the whole time he was on the show.
Obviously, that didn’t pan out well for him, and the former beauty pageant winner ended the relationship in a matter of weeks.
Clare And Dale - The Bachelorette Season 16 (????)
Ah, Clare Crawley and Dale Moss. They single-handedly created the messiest season of The Bachelorette, and their on again, off again relationship has been the source of a lot of speculation since the pair left the show together only a few episodes into Clare’s season.
I’m guessing Clare had to return the ring after their first breakup, but did she get it back when they got back together? Probably not. The couple is allegedly separated now, meaning it hasn’t even been two years since the premiere of Crawley’s season of The Bachelorette. The producers likely took the ring back, assuming Clare didn’t do something wild like burn it in effigy.
Tayshia And Zac - The Bachelorette Season 16 (1 Year)
This one is truly heartbreaking for me. Tayshia Adams, who appeared on The Bachelor before taking over Clare Crawley’s spot on Season 16 of The Bachelorette, was put in an uncomfortable position as the co-host of Katie Thurston’s season. During the Men Tell All, co-host Kaitlyn Bristowe asked Adams why she wasn’t wearing her ring, after which Adams made a tearful exit off the stage, letting fans in on the fact that she and Zac Clark were no longer engaged.
There are plenty of scripted moments in The Bachelor, but Tayshia's reaction seemed completely genuine. This is one couple I really wish could have made it down the aisle before things went south.
Katie And Blake - The Bachelorette Season 17 (6 Months)
Katie and Greg — sorry, I mean Katie Thurston and Blake Moynes — left Season 17 of The Bachelorette engaged, but announced shortly after that they were no longer together. Katie then shocked Bachelor Nation by making her new relationship with Bachelor franchise alum John Hersey public during her “12 Days of Messy” posting spree on Instagram.
There seemed to be a bit of bad blood between Katie and Blake, who was “frustrated” that she hadn’t discussed her new relationship with him prior to going public. Sorry, Katie. That ring definitely has to go back.
The next Bachelor franchise season airs on ABC in July, which will be the first season of The Bachelorette with two leads for the entire season. Will we add more happy couples to the list of Bachelor contestants who got to keep their rings? Or will we have to send another Neil Lane diamond to the ring graveyard?
Previous seasons of The Bachelor, The Bachelorette, and Bachelor in Paradise are available to stream with a Hulu subscription.
She/her. Lover of female-led comedies, Saturday Night Live, and THAT scene in Fleabag. Will probably get up halfway through the movie to add more butter to the popcorn.
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