Ashley & Jared's Bachelor Relationship Timeline Is Full Of Ups & Downs

As a contestant on Chris Soules' Bachelor season, Ashley became part of Bachelor Nation before Jared. He joined immediately afterward, appearing on Kaitlyn Bristowe's season of The Bachelorette.

Ashley said in The Story of Us that she was attracted to Jared when she saw him on The Bachelorette. She even attended a live taping of one of the episodes and asked the producers about him.

Ashley and Jared officially met when they competed on Bachelor in Paradise Season 2. "I remember walking down the steps in Paradise and seeing him at the bar and it was the weirdest feeling. I was just so gravitated and drawn to him. It was truly love at first sight," Ashley said in The Story of Us video.

Ashley pursued Jared throughout that season, but the feelings weren't mutual. After choosing not to have sex in the Fantasy Suite, Jared ended things with Ashley and they both left Paradise single.

After Bachelor In Paradise, the two continued hanging out, with Jared occasionally being interested in Ashley. He discussed how he was attracted to Ashley when she hosted a charity event at her parents' house in October 2015. Later that night, they danced on the bar and Ashley posted the video evidence on Instagram. Jared admitted in The Story of Us, "I wanted you that night."

In between their appearances on Bachelor in Paradise Seasons 2 and 3, things became more complicated between Jared and Ashley. In The Story of Us, they reminisce about making out in Boston toward the end of 2015 and going on their first official date to see Deadpool in early 2016. But Jared put an end to romantic things because he was in a "confused place."

Because of all the back-and-forth, Ashley was still emotional about Jared when they both appeared on Bachelor in Paradise Season 3. She cried when he started seeing Caila and tried to move on with Wells, but neither Jared nor Ashley's BiP Season 3 relationships lasted.

Ashley said that she decided to move on from Jared around March 2017, but they remained friends and Ashley often posted Instagram photos of them hanging out.

During Bachelor: Winter Games, which aired in February 2018, it seemed like Ashley had finally found happiness with Canadian contestant Kevin Wendt. While Ashley was busy in the snow, Jared did Bachelor In Paradise: Australia. He said in The Story of Us that he chose to do Paradise: Australia after Ashley decided to do Winter Games, implying he was growing to care for her romantically again.

Based on their social media accounts, Jared and Ashley have made it a tradition to go to St. Lucia with their Bachelor friends Jade and Tanner Tolbert. In 2018, they didn't post any photos of one another on their annual trip and that might be because they were (again) in a complicated place.

Jared admitted in The Story of Us that it was at this point — after Ashley was dating someone else — that he realized how much he cared about her. Despite the fact that she had a boyfriend, he decided to tell Ashley how he felt and even kissed her at the airport when they were leaving at the prompting of Tanner and Jade.

Though Ashley was moved by Jared's admission of feelings, she continued to date Kevin. But by March, the two had called it quits. In The Story of Us, Ashley said, "I did not cheat on Kevin. I ended the relationship because it had run its course. And then, Jared was still there." Jared then made some grand gestures to prove his feelings for Ashley.

Two months after Ashley's relationship with Kevin ended and nearly three years after Jared and Ashley met, they announced that they were dating. Kevin even congratulated the pair on Instagram.

After becoming boyfriend and girlfriend, Jared wasted no time committing the rest of his life to Ashley when he proposed to her on the beach in Mexico where they had met years earlier. The world got to see the moment a few months later in September when it aired as a part of Bachelor in Paradise Season 5.

Ashley and Jared made the bold decision to have their parents meet while stuck together on a family cruise.

Jared and Ashley adopted a pup, who they named Lois Lane. (Jared's family dog is named Clark Kent.) Lois has a sibling in the form of Ashley's dog — and Jared's "son through marriage" — Gurgi.

The couple joined creative forces to write a children's book called Lucy & Clark: A Story of Puppy Love, which follows the adventures of Clark and Ashley's first dog, who died. A percent of proceeds went to support no-kill animal shelters.

They may have announced they were dating in May 2018, but the two really got together in March, which Ashley commemorated with an Instagram post.

For Ashley's second KineticTV show, she and Jared enlisted the help of their Bach Nation friends Nick Viall and Jade and Tanner Tolbert. The first episode documented Jared moving in with Ashley and her sister Lauren, another Bachelor alum who has since moved out.

The couple tied the knot in an elegant ceremony in Jared's home state of Rhode Island with a ton of Bachelor alums in attendance. They then honeymooned in Italy and Greece.

Through her partnership with Modern Fertility, Ashley announced that she and Jared plan to start trying to have children in 2020. This confirms what she told HollywoodLife in December 2019, when she said they wanted to start a family "sooner rather than later" and already have a baby name picked out.

The couple quarantined with Ashley's parents in Virginia, where they spent most of their free time making TikToks for their shared account and recreating scenes from movies like The Wolf of Wall Street (above), Rock of Ages, Hairspray, and How to Lose a Guy in 10 Days.

After 13 weeks, Ashley praised her husband for surviving that much time with his in-laws. “I think he deserves a round of applause for getting out of it sane!” she captioned an Instagram post. “Honestly, we’re not even itching to leave, but we’re also looking forward to living just as a couple again.”

One of Ashley and Jared’s first dates was inspired by La La Land. They went to Griffith Park in Los Angeles, and Ashley even wore a yellow dress. “Fast forward to today, we went back to the same spot for the first [time] since being husband and wife,” Jared wrote on Instagram. “Ashley still wore the same yellow dress.”

In honor of their first anniversary, Ashley shared a gallery of photos from their special day while Jared posted their wedding video.

Ashley announced that she stopped taking birth control in an ad for the Natural Cycles app, which meant she and Jared were planning to expand their family. Later that month, the two vacationed around New England and mentioned the possibility of moving back to the East Coast. (Jared is from Rhode Island.)

For her partnership with Modern Fertility, Ashley shared that she took a test to determine the number of eggs she had. Her doctor told her not to wait more than a year before trying for her first baby, especially because she and Jared want multiple children.

Thanks to Ashley and Jared's time on Bachelor in Paradise, their first kiss was caught on camera. They decided to take a walk down memory lane and rewatch that footage, sharing a reaction video on Dec. 16. For Jared, it was his first time viewing the scene since the show aired in 2015, while Ashley hadn't seen it in "a few years." Both were left adorably embarrassed, and Ashley noted on Instagram that she "will never get over" two "cringe-y" elements she brought to their momentous kiss.

When Ashley got pregnant, the couple did a series of announcements in partnership with Amazon Live. On July 15, 2021, Ashley said Jared “did not believe” the news at They then took turns telling the story of how she took multiple tests to be sure.

The following month, on Aug. 26, 2021, the couple also live-streamed their gender reveal on the same platform. “We’re having a boy!” Jared shared while pulling down an “It’s a boy” balloon.

On Jan. 18, the couple once again took to Amazon Live to share more exciting baby news: They revealed their son’s name, Dawson Demitri Haibon, weeks before his birth. “I came up with the name as a 20-year-old,” Ashley shared, revealing that Dawson actually comes from Leonardo DiCaprio’s most famous role as Jack Dawson in Titanic — “One of Ashley’s loves,” according to Jared.

Finally, on Monday, Jan. 31, the couple welcomed their baby boy, almost two weeks shy of his February due date. Jared shared the news on Instagram, writing, “Baby Dawson is here and healthy! Ashley is recovering and doing well! It really couldn’t have gone much smoother.” He added, “He’s so sweet & beautiful and has been sleeping all day. Unlike his Mom and Dad who are on no sleep right now but it’s totally worth it!”

Ashley and Jared made a surprise return to where it all began on Bachelor in Paradise Season 8. Don’t worry, they’re not newly single — just enjoying a couple’s vacay. “Our relationship definitely has taken a backseat over the past 8 months,” Jared wrote on Instagram. “Not in a bad way, I love Ashley even more today than I did when we got married. She’s an incredible mother, a loving wife and my biggest supporter. But we haven’t had any ‘us’ time. We haven’t really been able to go on dates much, watch movies on the couch. Ya know, doing couples things.”

While on Paradise, Ashley and Jared have provided the latest generation of singles with advice — and perspective. “I can only hope the couples down in paradise find the same amount of happiness I’ve found after leaving the beach,” Jared added.

Additional reporting by Rebecca Patton and Kayla Blanton.