People.com Entertainment TV These 'Bachelor/ette' Contestants Didn't Find Love the First (or Second) Time Around, So They Tried Again If at first you don't succeed, try again ... and again. And maybe one more time. By Andrea Wurzburger Published on March 2, 2020 10:30 AM Share Tweet Pin Email 01 of 13 Clare Crawley Clare Crawley. Paul Hebert/ABC Total Number of Tries: 5 The newest Bachelorette isn't a new face to the franchise. Fans were first introduced to Crawley in 2014 on season 18 of The Bachelor as she vied for Juan Pablo Galavis' heart. She made it to the final two before their heated split, during which time she told Galavis' she'd "lost respect" for him. She got her second and third shots at love when she appeared on Bachelor in Paradise's first and second seasons in 2014 and 2015. She departed the show early both times, prompting her to announce that she would be retiring from the franchise. They never can stay away for long, though! Crawley returned to the franchise when she competed in The Bachelor Winter Games in 2018, and she ended up engaged to Benoit Beauséjour-Savard. Their engagement came as a surprise to viewers, as despite seeing the pair connect during their time on the spinoff show, their relationship did not get off to a good start. At the time, Beauséjour-Savard was open about his feelings for Crawley, but she ended up telling him that she didn't feel the same way and wanted to get to know German contestant Christian Rauch better. The devastated French-Canadian left the show, but later proposed during The Bachelor Winter Games: World Tells All. They split two months later. Announcing her Bachelorette news on March 2, 2020, Crawley told Good Morning America co-hosts what she's looking for this time around, explaining, "I want a man that will take off his armor. I want a man that is strong but is willing to take off the body armor, open themselves up and be vulnerable. I think that is some serious strength right there." 02 of 13 Hannah Brown RB/Bauer-Griffin/GC Images Total Number of Tries: 2 Hannah first appeared on Colton Underwood's season of The Bachelor, where drama between her and Caelynn Miller-Keyes kept her from getting the final rose. She was the most recent Bachelorette, though she is currently single after finding out that the man she chose, Jed Wyatt, went on the show with a girlfriend. But all hope was not lost for Alabama Hannah - in the premiere of Peter Weber's season of The Bachelor, the man of the hour asked her to come back and compete on the show. The episode ended in a cliffhanger that resolved a few weeks later with her deciding to walk away. 03 of 13 Nick Viall Total Number of Tries: 4 Viall first tried his luck at love on Andi Dorfman's season of The Bachelorette. He received the first impression rose and professed his love for Dorfman, but lost out to Josh Murray in the end. The following year, he asked Kaitlyn Bristowe to give him a chance on her season of The Bachelorette and again finished second. But hope was not lost for Nick, who then showed up on Bachelor in Paradise, hoping to find love with Amanda Stanton (who appeared on Ben Higgins' season), but she rejected him for Josh Murray. Yikes. Viall got his chance once more when the tables turned and he became The Bachelor. Unfortunately, Viall's romance with winner Vanessa Grimaldi did not last. 04 of 13 Brad Womack Brad Womack. Edward Herrera/ABC/Getty Total Number of Tries: 4 Womack famously ended his first season (season 11) as The Bachelor by rejecting both of the finalists, denying viewers their fairytale ending. His love story wasn't over, though, and he is the only bachelor to ever have two full seasons devoted to his quest for "the one." When he returned for season 15, he ended up proposing to Emily Maynard, but the pair broke up 8 months after their engagement. 05 of 13 Becca Tilley Becca Tilley. Steve Granitz/WireImage Total Number of Tries: 2 The California native competed for Chris Soules' heart on the 19th season of The Bachelor, but unfortunately did not get the final rose. Not to be discouraged, she returned for Ben Higgins' season the following year, but was eliminated before getting to bring Ben back to her hometown. 06 of 13 Amber James Rick Rowell/Walt Disney Television via Getty Total Number of Tries: 3 James first appeared on Chris Soules' season of The Bachelor and was unlucky in love. She followed in the footsteps of many former contestants and headed to Paradise in search of some summer lovin'. When she returned empty-handed, she tried again on Ben Higgins' season of The Bachelor, and was eliminated in week 4. 07 of 13 Ashley Iaconetti Steve Granitz/WireImage Total Number of Tries: 4 She is currently living out her fairytale with fellow Bachelor Nation alum Jared Haibon, but before she found love (away from the cameras), Iaconetti tried four times on camera. First, Ashley I. competed on Chris Soules' season of The Bachelor, only to be eliminated in week 6. Then, she traveled to Paradise not once, but twice, both times attempting to win the affections of Haibon but coming up short. Most recently, Iaconetti won Bachelor Winter Games with former Canadian bachelor, Kevin Wendt. Her relationship with Wendt did not last, but she did end up rekindling her romance with Haibon, and the two got married this summer. 08 of 13 Jared Haibon Noel Vasquez/Getty Total Number of Tries: 4 After joining season 11 of The Bachelorette, Haibon went on Bachelor in Paradise for seasons 2 and 3, but quit both seasons in week 5. Throughout his time in Paradise, though he made connections with other women, he dealt with a whole lot of Ashley I.-related drama. He also filmed Bachelor in Paradise: Australia, where he got caught in a love triangle and then refused to give either woman involved a rose. He found his way back to Ashley I. and the two married this summer. 09 of 13 Christen Whitney AFF-USA/Shutterstock Total Number of Tries: 3 Christen originally competed on Nick Viall's season of The Bachelor, but is probably best known for her time on season 3 of Bachelor in Paradise, where the other women called her "Scallop Fingers," and she left without a proposal. She appeared again on season 4 of the show, but was unfortunately did not meet her match. 10 of 13 Derek Peth DEREK PETH Total Number of Tries: 3 Peth headed back to Paradise for season 6, though left in week 4. He first appeared on JoJo's season of The Bachelorette, but was sent home in week 6. His first time in Paradise (season 4) ended with an engagement to Taylor Nolan, but the pair announced their split in June 2018. 11 of 13 Wills Reid Craig Sjodin via Getty Total Number of Tries: 3 Reid was a fan favorite on Becca Kufrin's season of The Bachelorette, but was unfortunately sent home in week 7. Hoping he would find love in Paradise, Wills appeared on the show for season 5, only to be eliminated in the first week. On his next visit in season 6, he made it just one week further, heading home in week 2 12 of 13 Bibiana Julian Craig Sjodin/ABC via Getty Total Number of Tries: 4 The feisty contestant was eliminated from Arie Luyendyk Jr.'s season of The Bachelor in the third week of the competition, but tried her luck during Bachelor Winter Games that year. She walked away without a significant other (and a little chilly) and decided to try her luck in warmer weather. Julian appeared on Paradise season 5, but was eliminated in week two. She joined the cast for season 6 of Paradise - but went home in week 1. 13 of 13 Jubilee Sharpe Total Number of Tries: 3 Sharpe has walked away without a match three times. The first was when she competed on Ben Higgins' season of The Bachelor and was sent home in week 5. Then, she gave Paradise a try two times - once in season 3 and again in season 5 - only to come away without finding love.