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Alex Michel: The Bachelor, Season 1 (March 2002)
Not even the first season of the entire franchise featured a proposal. Bachelor Alex Michel did not propose to Amanda Marsh, but he did pick her over Trista Rehn at the end of the six-episode season. They dated for a year before sadly breaking up.
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Aaron Buerge: The Bachelor, Season 2 (September 2002)
Anybody remember Aaron Buerge? He did propose to his chosen lady, Helene Eksterowicz (who we also don't remember), but they broke up after a few months, before the finale even aired.
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Trista Rehn: The Bachelorette, Season 1 (January 2003)
Trista Rehn returned after "losing" season one of The Bachelor for her own shot at love, and boy did she find it! Runner-up Charlie Maher didn't stand a chance against Ryan Sutter, who Rehn then married in December of the same year. They are miraculously still together with two kids!
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Andrew Firestone: The Bachelor, Season 3 (March 2003)
Andrew Firestone is the first Bachelor whose name we actually remember! Unfortunately, his relationship with Jen Schefft did not pan out after his proposal, because they broke up after just a few months.
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Bob Guiney: The Bachelor, Season 4 (September 2003)
One of Trista's rejects from The Bachelorette, Bob Guiney, got his own time in the love-finding spotlight, but he didn't end up proposing to his winner, Estella Gardinier. He did, however, give her a promise ring, which is only one of the most high school things that has ever happened on this show. Their promise did not last long, and they broke up shortly after the show aired.
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Meredith Phillips: The Bachelorette, Season 2 (January 2004)
Meredith Phillips got a second chance after being sent home by Bob Guiney, and did get engaged to Ian McKee. Their relationship sadly only lasted a little over a year.
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Jesse Palmer: The Bachelor, Season 5 (April 2004)
Football player Jesse Palmer was known for being the first non-American Bachelor (because he was Canadian) and also for forgetting a woman's name during the first rose ceremony. He eventually chose Jessica Bowlin over runner-up Tara Huckeby, but he didn't propose and they broke up after just a few weeks.
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Byron Velvick: The Bachelor, Season 6 (September 2004)
A tale of two Bachelors—As it turns out, Kaitlyn and Britt were not the first! Fisherman Byron Velvick (what a name!) won out over Jay Overbye when the women got the chance to vote. Byron proposed to Mary Delgado, who also competed in season four, in Spanish so that her Cuban parents could understand. She accepted, but they never actually married before breaking up in 2009.
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Jen Schefft: The Bachelorette, Season 3 (January 2005)
Jen Schefft returned after her breakup with Andrew Firestone to sift through her own batch of suitors. In the end, she didn't pick any of them. Jerry Ferris did propose to her after she finally decided he was better than runner-up John Paul Merritt during the live final episode, but she rejected his proposal.
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Charlie O'Connell: The Bachelor, Season 7 (March 2005)
Actor (and Jerry O'Connell's little brother) Charlie O'Connell did not propose to Sarah Brice at the end of his season. They did, however, start dating. They broke up in 2007, got back together in 2008, then broke up again in 2010.
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Travis Stork: The Bachelor, Season 8 (January 2006)
Dr. Travis Stork did not propose to Sarah Stone during his season set in the oh-so-romantic city of Paris, and they broke up shortly after the show aired. Stork went on to appear on The Doctors and is married to another doctor, so he's probably doing just fine.
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Prince Lorenzo Borgheze: The Bachelor, Season 9 (October 2006)
Prince Lorenzo Borgheze courted his bachelorettes in Rome, during a string of themed seasons. He did not propose to Jennifer Wilson, and they broke up after just a few months of dating.
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Andrew Baldwin: The Bachelor, Season 10 (April 2007)
Naval officer Andrew Baldwin proposed to Tessa Horst during the finale, but they called off the engagement a month later. The relationship lasted another few months before they were done for good.
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Brad Womack: The Bachelor, Season 11 (September 2007)
Brad Womack's (first) season is one of the show's most infamous seasons due to the fact that Brad didn't choose anyone. He rejected both DeAnna Pappas and Jenni Croft, and everybody went home alone after the most dramatic finale so far.
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Matt Grant: The Bachelor, Season 12 (March 2008)
British hunk Matt Grant proposed to Shayne Lamas in a relatively uneventful finale, drama-wise, aside from runner-up Chelsea Wanstrath calling Shayne "the fakest girl on the show." Even their break-up was perfectly amicable, and they claimed they would remain friends.
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DeAnna Pappas: The Bachelorette, Season 4 (May 2008)
After being rejected by Brad Womack, DeAnna Pappas managed to find love for one hot second with Jesse Csincsak, while Jason Mesnick was left as the runner-up. In a completely-the-opposite-of-shocking turn of events, DeAnna and Jesse broke up after just a few months of dating.
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Jason Mesnick: The Bachelor, Season 13 (January 2009)
In another infamous season finale, DeAnna Pappas' reject, Jason Mesnick, first proposed to Melissa Rycroft. He then changed his mind and asked original runner-up, Molly Malaney, for a second chance. They later got engaged, and are—you're never going to believe this—still together! They even have kids!
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Jillian Harris: The Bachelorette, Season 5 (May 2009)
Jillian Harris, Jason Mesnick's reject and the first foreign/Canadian bachelorette, said yes to Ed Swiderski after he proposed to her in the finale. Ed might also be remembered for having to leave in week 5 in order to keep his new job with Microsoft, but he managed to return in week 7. That should have been a sign of true love or something, but Jillian and Ed were broken up a year later. Ed did recently get married though, so good for him!
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Jake Pavelka: The Bachelor, Season 14 (January 2010)
Ah yes, The Bachelor: On the Wings of Love, aka the best themed season yet. Hot pilot and Jillian Harris reject Jake Pavelka endured many plane jokes in his search for love, eventually proposing to Vienna Girardi. They split a few months later.
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Ali Fedotowsky: The Bachelorette, Season 6 (May 2010)
After quitting on Jake Pavelka in order to keep her job, Ali Fedotowsky returned to the show and ended up engaged to Roberto Martinez. Their engagement lasted about a year and a half before they called it quits.
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Brad Womack: The Bachelor, Season 15 (January 2011)
Womack is back! After leaving season 11 alone, Brad Womack returned to try again. Things went a little better for him after proposing to Emily Maynard over Chantal O'Brien, though they broke up before the season was even done airing. They got back together later, and then broke up again just a couple months later. Poor Brad Womack.
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Ashley Hebert: The Bachelorette, Season 7 (May 2011)
After losing out on Brad "Forever Alone" Womack, Ashley Hebert actually managed to successfully find love with J.P. Rosenbaum after rejecting Ben Flajnik. J.P. proposed in the finale, she said yes, and they were married on TV in 2012. They had two kids together and lasted for eight years before calling it quits in 2020.
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Ben Flajnik: The Bachelor, Season 16 (January 2012)
Winemaker and Ashley Hebert's runner-up Ben Flajnik did propose to Courtney Robertson in the season 16 finale, but they couldn't even wait for the show to finish airing before they broke up. They tried again, and even got engaged again, but they were over by October. Sad.
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Emily Maynard: The Bachelorette, Season 8 (May 2012)
After breaking up with Brad Womack twice, Emily Maynard got a second (third?) chance when the show moved production to her hometown of Charlotte, North Carolina so she could be near her daughter. She ended up engaged to Jef Holm after he proposed, but they only lasted til October.