The Bachelorette was filmed in a bubble this season which means we won’t get to see any lavish travel dates. However, the producers still managed to subject past contestants to COVID-19 testing and quarantine in order to include one Bachelorette hallmark: heartfelt chats with fan favorites from Bachelor Nation. Stepping in to fill that role is season 3 Bachelorette DeAnna Pappas. The former lead stops by in episode 3 to give Clare Crawley some tips and, let's be honest, the standard pep talk about being open to possibilities on this Journey. While newer Bach fans may not recognize (or remember) DeAnna, she's actually the perfect advisor for Clare. They have very similar past experiences with this franchise — plus, DeAnna knows a thing or two about falling hard and fast, like Clare and a certain suitor whose name rhymes with kale.
Like Clare, DeAnna made it through a controversial Bachelor season. She was one of the two final women on The Bachelor's 11th season, on which then-Bachelor Brad Womack famously dumped both of his remaining contestants and opted to leave the show without proposing. Naturally, DeAnna was heartbroken and shocked on finale day.
After that harsh public rejection, DeAnna became the fourth ever Bachelorette in 2008, where she met her future fiance Jesse Csincsak. Although she did not give her first impression rose to Jesse or tell Chris Harrison she'd just met her husband on limo night, like Clare did with Dale, it was obvious early on that DeAnna had the strongest connection with Jesse. But there were red flags that DeAnna ignored along the way: Jesse’s career as a professional snowboarder didn't mesh well with DeAnna’s lifestyle, and her family was incredibly skeptical of the relationship. Still, she was set on Jesse, so he made it to her season's finale alongside lovable single dad Jason Mesnick (who ended up becoming the next Bachelor). Fans were not too happy when, during that finale, she allowed Jason to get down on one knee before rejecting him. And they were equally upset that she accepted Jesse’s proposal. As we know now, DeAnna and Jesse broke up just a few months later.
In fact, there are few past Bachelorettes who'd be more perfect than DeAnna to come in for the yearly advice chat, and to offer a word of caution about going all in on a suitor from the beginning. And that certainly seems to be where the show is going: In the main teasers for Clare’s season, one of the guys appears to complain that Dale is not trustworthy. The clip of the roast in week 3's episode also hints at Dale being widely disliked by the other men. Bringing on the past Bachelorette who famously made a lamentable choice would fit pretty well into the budding Clare-may-be-making-the-wrong-choice storyline. Clare hasn't even made it to hometowns (and as we now know, she won't), and already, fans and suitors alike have been skeptical about her instant attraction to Dale. DeAnna also knows a thing or two about getting through negative attention after her finale.
DeAnna's story also holds a flicker of hope, should Clare's romance with Dale be doomed as the promos keep trying to predict: she did actually find love via Bachelor Nation. She married Stephen Stagliano, the twin brother of Bachelorette season 5 contestant Michael. They have two kids together — both are frequent stars of her Instagrams — and DeAnna now runs a blog.
Few people searched for love on this franchise the way Clare has, other than DeAnna, so who better to step up to the plate (and go through all the grueling safety steps) to talk Clare through what could happen?