After Brad Womack said goodbye to Ashley Hebert in South Africa on season 15 of The Bachelor, he ended up proposing to Emily.
Then Ashley was named the new Bachelorette. And, as she gets to know her own set of suitors, Emily – whose relationship with Brad is "off and on" – has had an unexpected influence on Ashley's rocky search for love.
On Monday's episode of The Bachelorette, Ashley invited the men to a comedy club, where they were expected to roast her. When William got up on stage, he was eager to make the crowd laugh. Instead, he made Ashley cry.
"I thought I signed up to be with Emily," he said, "and then Ashley's here – really who gives a f––."
"It hurt me that William did not use great judgment," Ashley said in her Bachelorette blog for PEOPLE.com.
Later in the episode, Ashley explained her tears to Bentley: "I'm just scared that I let you guys down because it's me here and not Emily," she said. "That was my biggest insecurity that first night."
Bentley may have offered Ashley a shoulder to cry on but he's certainly not helping out in the insecurity department. "With 25 guys, I promise you, at least 24 of them were really excited it was you," he told her on the show, before leaving her behind.
What he didn't say was that he could only promise with such certainty because he considered himself the 25th guy. "Ashley's a sweet girl, but there's no question that Ashley doesn't have the checklist that I'm looking for in a future wife," he said in a previous episode. "I can tell you right now it's not gonna work. I, to be honest with you, could almost care less. Things could've turned out differently if the Bachelorette was Emily."