'Bachelor(ette)': 20 'Two-Timers'

Trista Rehn

Bachelorette season: 1
Bachelor season: 1
Rejected by: Alex Michel
Believe it or not, The Bachelorette's biggest success story started out as The Bachelor's biggest sob story. Trista first became known in Bachelor fandom as the girl who didn't get the guy after making it to the final two with season one's Alex Michel. However, that didn't stop her from finding true love as the first ever Bachelorette. Ten years later, Trista and husband Ryan Sutter have two kids and go down as this show's most successful love story. They even had their own ($4 million) wedding ceremony televised by ABC. Not too shabby.

Bob Guiney

Bachelor season: 4
Bachelorette season: 1
Rejected by: Trista Rehn
Bob was the funny guy who knew how to own a room, but he couldn't quite figure out how to beat out the competition for Trista's heart. He didn't seem to mind all that much, so long as people were laughing and the drinks were flowing. When it came time for him to be the Bachelor, the good times kept rolling. Despite rumors that Bob slept with more women than any other Bachelor, he did end his season by giving a promise ring to Estella Gardinier. That promise was later broken. (SPOILER: It would become a franchise trend-slash-punchline.)

Meredith Phillips

Bachelorette season: 2
Bachelor season: 4
Rejected by: Bob Guiney
After signing up for Bob's season of The Bachelor at the last minute, Meredith made it all the way to being crowned third runner-up. But the former model and chef had charmed her way into the hearts of viewers, which made her the perfect choice as the second ever Bachelorette, where she chose Ian McKee. After living together for almost a year, Phillips and McKey ended things.

Jen Schefft

Bachelorette season: 3
Bachelor season: 3
Rejected by: Andrew Firestone
Another of the chosen ones gone wrong, Jen knows what it feels like to receive a final rose from one of the richest Bachelors to ever grace our television screens. However, she also knows what it feels like to have that relationship end and then embark on her own journey as the Bachelorette. The second time around, she left the show without a ring, but that's another story.

DeAnna Pappas

Bachelorette season: 4
Bachelor season: 11
Rejected by: Brad Womack
After Brad let go of Phoenix Suns dancer Jenni Croft, viewers (and DeAnna) were certain that Brad was going to get down on one knee and propose. After Brad started sweating a little more than usual, frantically loosening his tie, and walking away to get some air, DeAnna got the feeling something was amiss. In the end, Brad wasn't ready to say those three words to DeAnna so instead, he said six, ''I have to tell you goodbye.'' Once DeAnna was in charge, she chose the long-haired snowboarder Jesse Csincsak and, well, it didn't work out. However, she's now married to the twin brother of Michael Stagliano, the dancer from Jillian Harris' season. It's a tangled web we weave?when we allow ourselves to believe that you can find love on reality TV.

Jason Mesnick

Bachelor season: 13
Bachelorette season: 4
Rejected by: DeAnna Pappas
The single father with a heart of gold made it all the way to the final rose ceremony, where he even went so far as to get down on one knee and pull out a ring?box. Before he could get any further, DeAnna said three little words: ''No, I can't.'' Jason then got rejected in what goes down as one of the most painful goodbyes the show has ever seen. It was only the start of the drama for Jason, who proposed to Melissa Rycroft at the end of his Bachelor season, only to change his mind and pick his runner-up Molly Malaney at the taping of After the Final Rose. Now his many, many tears are from joy — Jason, Molly, and Jason's son Tye (from a previous marriage) welcomed baby girl Riley Anne in March 2013.

Jillian Harris

Bachelorette season: 5
Bachelor season: 13
Rejected by: Jason Mesnick
Jillian's bubbly personality and active sense of humor caught the attention of both Jason and the viewers. However, she didn't hold Jason's attention for long, which might not have been the worst thing, considering she inadvertently saved herself from getting Mesnicked. Back as the Bachelorette, Jillian chose Ed Swiderski, whom tabloids painted as a huge flirt. The couple didn't last, but Jillian and her nose job are perfectly happy with her current man, a snowboard instructor.

Jake Pavelka

Bachelor season: 14
Bachelorette season: 5
Rejected by: Jillian Harris
The talking six-pack with an affinity for spontaneous first kisses seemed like a sure thing for the upbeat Jillian. But, after Jillian admitted to having a preference for bad boys, viewers started to fear for the good guy. That fear turned out to be valid, when Jillian let Jake go, but this good guy wasn't going down without a fight. Jake returned to the show to tell Jillian that her favorite bad boy Wes had a girlfriend. In the end, she still chose the bad boy?for at least a little while longer. During a Bachelor season hilariously subtitled ''On the Wings of Love,'' Jake went on to choose his own bad girl in Vienna Girardi. Let's just say their relationship went sour quicker than a pint of milk left out in the Texas summer. Perhaps he should've learned something from Jillian.

Ali Fedotowsky

Bachelorette season: 6
Bachelor season: 14
Rejected by: Jake Pavelka
From her first one-on-one, it was clear that Ali was a frontrunner to win Jake's heart. It was also clear that she was becoming sworn enemy number one of eventual winner Vienna. After making it to the final four, Ali had to make the tough call of returning to work or losing her job and continuing her journey with Jake. She chose her job, a decision she would later regret when she called Jake to ask for the chance to return. By that point, though, his heart knew what it wanted?and it was someone a bit younger. For her second try at love on The Bachelorette, Ali chose the super sexy Roberto Martinez. The couple stuck it out for a little over a year (including several engagement extensions), but their love wasn't built to last either.

Brad Womack

Bachelor seasons: 11 & 15
Rejected by: Himself
When the Texas bar owner first showed up on The Bachelor scene, viewers were wooed by his Southern accent, downhome charm, and marquee good looks. Yet, after a season full of what seemed to be genuine relationships, Brad opted out of getting down on one knee during his final rose ceremony, saying goodbye to both Jenni and DeAnna. Brad returned to play with America's emotions again, proposing to Emily Maynard only to break off the engagement (he insisted he was at fault) within a year.

Ashley Hebert

Bachelorette season: 7
Bachelor season: 15
Rejected by: Brad Womack
An early favorite of Womack 2.0, Ashley quickly established herself as the adorable girl with mighty ambition. Eventually Brad's hard-hitting questions derailed their final overnight date, doing irreparable damage done to the relationship. Brad pulled her away for a last-minute chat before the next-to-last rose ceremony, where he came to the conclusion that he didn't fit into her life. There were too many questions left unanswered, so he sent her packing. The good news? Thanks to her stint on The Bachelorette, she's now married to J.P. Rosenbaum. Yay for love!

Ben Flajnik

Bachelor season: 16
Bachelorette season: 6
Rejected by: Ashley Hebert
This Sonoma winemaker made it all the way to the end only to get down on one knee before realizing his love was unrequited. Refreshingly, Ben wasn't scared to show his anger at the caught-on-camera rejection. The audience ate it up, and the show found its next Bachelor. Sadly, Ben lost all sympathy when he dove into every dating-show cliché during a skinnydipping session with manipulative model Courtney Robinson (a.k.a. the girl who constantly referred, Charlie Sheen-style, to herself ''winning!''). They both turned about to be losers, and the relationship withered faster than the final rose.

Emily Maynard

Bachelorette season: 8
Bachelor season: 15
Rejected by: Brad Womack?sort of
At the end of his second run as Bachelor, Brad finally found love?or so he thought. After choosing Emily Maynard and getting down on one knee in one of the show's sweetest proposals (''You're my once in a lifetime''), the couple showed up at the After the Final Rose ceremony with a little less love and a lot more tension. The two stubborn Southerners didn't end up making a perfect match, which led to Em giving it another go after the engagement ended. She chose skater boy entrepreneur Jef Holm. Stop me if you know where this is going...

Sean Lowe

Bachelor season: 17
Bachelorette season: 8
Rejected by: Emily Maynard
Sean's irresistible abs and sparkling blue eyes carryiedhim through to Emily's top three, but that's where his ''journey'' ended. When the often-shirtless poster boy returned as the one handing out the roses, he found love with current fiancé Catherine Giudici. Admittedly, they've kept the spark alive for less than six months at time of press, but they did make it through Sean's stint on Dancing With the Stars. That has to count for something, right?

Desiree Hartsock

Bachelorette season: 9
Bachelor season: 17
Rejected by: Sean Lowe
The early favorite lost major ground during a disastrous hometown date. Dealing with a good old-fashioned fake-ex-boyfriend prank? No problem for Sean. Dealing with Desiree's disapproving brother? Big problem. Sean let Des go at the next rose ceremony, setting her free to find a man who enjoys both pranks and verbal abuse. A girl can dream, right?

Juan Pablo Galavis

Bachelor season: 18

Bachelorette season: 9

Rejected by: Desiree Hartsock

On Desiree’s season of The Bachelorette, Juan Pablo was best known as "the hot soccer player/single dad." Since he never even got a one-on-one with Desiree, it was obvious that there wasn’t a strong connection brewing. But from what viewers saw of Juan Pablo in the house—cough, his abs—he quickly became a fan favorite. That is, until he became the Bachelor, and showed the world that he’s not as sweet as we once thought. And no, it’s not “okay.”

Andi Dorfman

Bachelorette season: 10

Bachelor season: 18

Rejected by: Juan Pablo Galavis

Juan Pablo and Andi connected early in the season, and they seemed to have everything going for them… until they spent a night together in the Fantasy Suite. According to Andi, Juan Pablo showed his true, very narcissistic colors, and she was over it. So when Andi got a second chance at love, America was cheering her on. Even though she said "stop" way too much, she somehow found love with Josh Murray. The two have since called it quits.

Chris Soules

Bachelor season: 19

Bachelorette season: 10

Rejected by: Andi Dorfman

Chris Soules made a name for himself on Andi’s season of The Bachelorette by being the "hot farmer" from Arlington, Iowa. Making it all the way to hometown dates, he wooed Andi with secret admirer notes, messages written in the sky, and a downright adorable family. However, it wasn’t enough for the hotshot lawyer. So when Chris became The Bachelor, he set out to find a woman who could live in a town of 500 for the rest of her life. And after a season lacking in dialogue, he did just that with Whitney Bischoff.

Kaitlyn Bristowe

Bachelorette season: 11

Bachelor season: 19

Rejected by: Chris Soules

Kaitlyn Bristowe arrived on night one of The Bachelor and immediately made a joke about hot farmer Chris plowing her fields. From there on out, we knew what kind of contestant we had on our hands. But when Chris sent her home, she was heartbroken. And now, she’ll compete against Britt Nilsson for the role of Bachelorette—and another chance at love.

Britt Nilsson

Bachelorette season: 11

Bachelor season: 19

Rejected by: Chris Soules

Britt was an early frontrunner in Chris’ season, getting both the first impression rose and a kiss on night one. From there, she seemed unbeatable, until finally, some of the other women in the house expressed their concerns that she didn’t actually want a life in Arlington, Iowa. Unsure of her sincerity, Chris then sent a hysterical Britt packing. Now she has a chance to become the first shower-free Bachelorette in history.