Let’s be honest: this season of the Bachelorette has left a lot to be desired. And while I like Hannah and I’m rooting for her, I want to take a moment to appreciate my all-time favorite Bachelorette seasons. I have not watched all 15 seasons, but I did watch the OG season with Trista Sutter (Trista Rhen back then) in 2003, so I’ve gotten a pretty good sampling of the past 16 (wow!) years of Bachelorette history. Without further ado, here are my top five favorite Bachelorettes!
#5 - Ashley Hebert (Rosenbaum) - Season 7
Ashley Hebert was an early favorite on Brad Womack’s second season of The Bachelor, where he eventually chose Emily Maynard, who also went on to become the Bachelorette when their engagement was called off. Womack really did a lot for this show despite being a boring turd to watch on screen. I related to Ashley because she absolutely could not contain her anxiety about the relationship. (Hello, me dating in my twenties.) She was chosen as Bachelorette over another fan favorite, Chantal, but I was excited it was Ashley. She was studying to be a dentist and seemed really down-to-Earth. She had great energy and was really funny, and she still feels like the most “normal” of all the past leads to me. Ashley is someone I’d hang out with.
Ashley’s season sticks out for a few reasons. In the early weeks, Ashley’s season had one of the most cringe-worthy group dates ever, wherein the men had to participate in a roast. The men did a fine job roasting one another, and most of them were okay at gently roasting Ashley, while still making it clear they liked her and wanted to, you know, potentially marry her at the end. But some didn’t. Will, a self-proclaimed roast fan, said, “Ashley: so beautiful, so gorgeous, so used. They say one man’s trash is another man’s treasure. I thought I signed up to be with Emily or Chantal and then Ashley’s here.” He, among others, also made jokes about Ashley’s small chest. Ashley ended up crying on the date and being fake-consoled by Bentley, the contestant she clearly liked best. But he decided to leave that night, telling producers that he wasn’t physically attracted to Ashley, and that he’d also been hoping for Emily. An iconic episode full of villain drama.
Drama aside, one of the best parts of Ashley’s season was watching her fall in love with JP Rosenbaum. Their one-on-one dates were actually fun to watch, and their connection felt really genuine. Turns out, it was. Ashley and JP got married in a televised (but still very lovely) wedding — only the second couple from The Bachelorette to make it to the altar — and now have two children. All in all, a successful season with a lead to root for.
Other notable contestants and connections: Ben Flajnik, who ended up being a very so-so Bachelor.
#4: Andi Dorfman - Season 10
I liked Andi Dorfman from the time she walked into the Bachelor mansion to compete for Juan Pablo’s affection. I liked her even more when she memorably eliminated herself after her overnight date because Juan Pabs was an egocentric asshole. Her famous “It’s not okay!” proclamation became her first book title. More on that later.
Andi’s turn as the Bachelorette was exciting because we thought we could expect some more no-nonsense breakups like the one with Juan Pablo. And it was also cool to see a Bachelorette with a high-powered career — Andi was an attorney — that she seemed to love. Andi had her shit together.
Andi’s season sparked one of the show’s more famous rivalries, Nick Viall versus Josh Murray. In the end, Andi chose toxic Josh, and the After the Final Rose special got particularly tense when runner-up Viall asked Andi on live television why she’d had sex with him in the fantasy suite if she knew she wasn’t going to pick him, noting they’d done “fiance-level stuff,” and I still want to know what that means.
Andi is one of my favorites perhaps because of everything that happened after her season. Andi capitalized on her Bachelorette status and wrote two New York Times bestselling books, It’s Not Okay and Single State of Mind. And while I didn’t care for her second book, It’s Not Okay gave some juicy insider knowledge on the man she picked (Josh called her a whore, for one thing) and on her time as a contestant on Juan Pablo’s season. Oh, and some details on banging Nick in the fantasy suite. It’s worth a read or a listen if you’re a Bach fan. (In other news, Josh is still a dick.)
Andi now lives in New York and appears to be happily single. I looked at her Instagram today to update myself, and she doesn’t even mention The Bachelorette in her bio -- just her bestselling books. Good job, Andi. Though I doubt she’d be interested, I would actually love to see ABC give Andi a do-over season.
Other notable contestants and connections: Chris Soules, who went on to become the Bachelor. Nick, of course, later competed on Kaitlyn Bristowe’s season and Bachelor in Paradise before becoming the Bachelor himself. Murray later got engaged to Amanda Stanton on BiP, who also wised up and got away from that dude and now appears to be good friends with Andi.
#3: Ali Fedotowsky (Manno) - Season 6
Ali sent herself home on sociopath Jake Pavelka’s season before her turn as the Bachelorette. It was cool to see a woman choosing her career over a very lame dude (even if she later tried to come back for said dude).
As the Bachelorette, Ali was fun to watch, and her season had one of the best 2-on-1 dates in the show’s history — a frozen tundra full of awkward between contestants Kasey Kahl and Justin Rego (perhaps better known by his wrestling name, Rated-R). Kasey, who’d coined a catchphrase of sorts, “guard and protect your heart,” was a little on the loony side, and Justin was not well-liked by the other dudes in the house. It’s a lose-lose for Ali, really. Ali said on the date that “The only thing Kasey has to do today is be normal.” And he didn’t. Kasey had gotten a TATTOO of the whole “guard and protect” thing, and he revealed it to Ali on the date. Ali was...not moved by this and gave Justin the rose, flying away with him and leaving Kasey sitting on a glacier. Epic elimination.
Ol’ Rated-R later had his own memorable moment when his girlfriend contacted the show. When Ali confronted him, he literally ran away from her, leg cast and all, refusing to face the situation. I tried so hard to find a gif of this.
Ali’s season also had one of the more hard-to-watch breakups, when frontrunner Frank Neuschaefer broke up with Ali right before their fantasy suite date because he still had feelings for his ex-girlfriend. He didn’t show up to After the Final Rose, either. While it didn’t work out with the hottie who proposed to Ali, Roberto Martinez, I found Ali’s season entertaining throughout. She’s now married to Kevin Manno, and they have two children together.
Other notable contestants and connections: Kirk DeWindt had that crazy taxidermy hometown date and later initiated a dramatic breakup with Carly Waddell (Bass) on BiP. Kasey went on to compete on Bachelor Pad and dated Jake Pavelka’s ex-fiancee, Vienna Girardi.
#2 - Rachel Lindsay - Season 13
Rachel was a major fan favorite on Nick Viall’s season. Rachel was an attorney in Dallas, and she was over 30, which was a refreshing turn. Also notably, Rachel was the first (and so far, only) black lead on the show. (Though all of us at #BSG are hoping we get our first black Bachelor in Mike Johnson!) Rachel was on record saying this status came with some pressure, but I think she handled it beautifully.
Rachel felt refreshingly real, and she came in knowing what she wanted and didn’t want in a husband. When DeMario’s girlfriend showed up, she was having none of his shit and told him to get the f*ck out. She also had a really solid group of men in her top 3 -- Eric Bigger, Peter Kraus and Bryan Abasolo. In fact, Rachel had one of the most solid groups of dudes overall, with more diversity and more age-appropriate men than any other season. But Rachel got the shaft for a few reasons in her season. 1. The show focused on Peter so much that we barely saw her relationship with Bryan, the man she chose, developing, and 2. The live finale event was pretty brutal, with us watching Rachel watch her own breakup with Peter live. It felt kind of icky at the time, but now we’ve seen Arie dump Becca on tape, so maybe this is just the direction the show is headed. Whatever ABC’s reason was, it only further took focus away from her actually successful relationship with Bryan. And Peter wasn’t even the Bachelor, so what’s the point?
Even though that part sucked to watch, the breakup was one of the more real-feeling moments from a show that often feels contrived.
Rachel has been pretty vocal since The Bachelorette on podcasts and other media about her experience on the show, which is another thing I love about her. She did the show and found her husband, but she is honest about some of the things she was uncomfortable and dissatisfied with. She’s a host on ESPN radio, still an attorney, and hitting us with Bach recaps on Strahan and Sara. She and Bryan Abasolo are getting married next month, which will make her the first Bachelorette since Desiree Hartsock Siegfried (Season 9) to marry the man she chose on the show.
Other notable contestants and connections: How can we forget Kenny King?! Between him and Peter, how the hell did ABC choose Arie to be the Bachelor?! Top-four finisher Dean Unglert competed (and was a total fuck boy) on BiP and Winter Games.
#1: Kaitlyn Bristowe - Season 11
Emily and I have said it in our recaps: Kaitlyn Bristowe was the best Bachelorette. ABC tried to screw with this season by doing the whole two-bachelorettes-let-the-men-vote thing, but thank goodness, the season overcame this misstep as soon as Kaitlyn took the helm.
Another over-30 Bachelorette, Kaitlyn was a clear fan favorite on Chris Soules’s season. She was hilarious, genuine, and most importantly, way too fucking cool for Chris Soules. Kaitlyn is infinitely likable and feels the most approachable of any of the show’s leads. I still wanna hang out and get wine drunk with Kaitlyn.
Her season was controversial for a few reasons, but the main one was the return of Nick Viall and what happened with him. Kaitlyn and Nick and been talking before she was cast as Bachelorette, and then they got in touch while she was actually on the show (Nick explains how this all happened on his podcast, The Viall Files), and Nick showed up several weeks into the season and asked to stay. Kaitlyn said yes, and her dudes were not happy. Then it got really interesting. During a one-on-one date, Kaitlyn invited Nick back to her room, and they had sex. Like mid-way through the season. Kaitlyn became the first lead to admit to having sex with a contestant while on the show.
Kaitlyn got a lot of shitty backlash from viewers over this, mostly of the slut-shaming variety, but she handled it well. She publicly said that she wasn’t ashamed for having sex, but that her guilt came from concern that it would hurt some of the other men’s feelings. The man she choose in the end, Shawn Booth, also publicly defended her, which was nice to see.
Even though ABC kept Kaitlyn and her men in Ireland for what seemed like forever and had the final rose ceremony back at the mansion, Kaitlyn remained entertaining and compelling until the end of the season.
Viall finished in second place for the second time — though he went on to be on BiP and The Bachelor — and Kaitlyn accepted Shawn’s proposal. They were engaged for a little more than three years before ending their relationship in 2018, which is pretty successful by Bachelorette standards.
Kaitlyn continues to be one of my favorite people from the show and has found a place in the entertainment world (where she belongs!) still keeping it real and making us laugh on her podcast Off The Vine With Kaitlyn Bristowe, where she interviews other Bachelor Nation members and various celebrities. She is currently in a relationship with Jason Tartick, a contestant from Becca Kufrin’s season of The Bachelorette.
Other notable contestants and connections: Kaitlyn had a good group of guys, including Ben Higgins (Bachelor Season 20), Tanner Tolbert (now married to Jade Roper Tolbert, a contestant with Kaitlyn on Chris Soules’s season), Ben Zorn (Emily and I still wish he would be the Bachelor), and Jared Haibon (marrying Ashley Iaconetti, another Chris Soules contestant, next month).
And there you have it: my top five favorite seasons. What’s your favorite season of The Bachelorette?!