Jesse's Journey So Far

Take a look back at Jesse’s 90 Day Fiance journey and watch his story continue on the new season of 90 Day: The Single Life every Monday at 8/7c!

Shop This Look

Photo By: TLC

We first met Jesse on the very first season of Before the 90 Days, when he welcomed his then-girlfriend, Darcey, to his home in Amsterdam. Eventually, the couple went their separate ways — and now, Jesse is ready to find love again. Look back at his journey and follow his latest dating adventures on the new season of 90 Day: The Single Life.

Jesse was ready to meet Darcey in person for the first time. He waited in the airport with roses and a welcome home banner.

Darcey arrived in Amsterdam and Jesse couldn't wait to show her around.

Darcey asked Jesse if he planned on changing his relationship status on social media. Although Darcey explained that the switch would mean a lot to her, Jesse wasn't on the same page.

Jesse took Darcey to meet his mom, Marian, and his stepdad, Dave. During dinner, Dave directly voiced his concerns about the couple's 18-year age gap and implied that Darcey wasn't in the same league as Jesse.

Jesse introduced Darcey to his buddy, Erdem, who had similar concerns. Erdem wondered if the couple would last despite their age difference.

Jesse video-chatted with Darcey's daughter, Aniko. Jesse knew that Darcey and her kids were a package deal, but he wasn't sure if he was ready to become a stepfather.

After a short period of dating, Jesse got down on one knee and...gave Darcey a promise ring? Darcey was in shock and a little confused about the sentiment, but Jesse wanted to show his commitment early on — even if it did look like a proposal.

On the Before the 90 Days Tell All, Jesse got heated as the couple revisited their big fight in Amsterdam.

Jesse made his way to America on the second season of Before the 90 Days.

Jesse revealed that he and Darcey broke up for a short time. He brought up Darcey's post-breakup behavior on social media and scolded her for it, and she left their dinner date to collect herself. Jesse had just arrived, but they were already bickering.

Jesse met Darcey's daughters, Aniko and Aspen, in person for the first time in New York City.

Jesse and Darcey argued about social media use again over dinner and Jesse left the restaurant this time. However, the pair made up shortly after.

Cut it on the bias! Jesse and Darcey arrived in Connecticut and planned a lovely family dinner for her girls. Unfortunately, the evening took a turn. Tensions were already high between the two and when Darcey told Jesse how he should cut the steak, it was the final straw.

A "shoe throwing" incident led to another big fight and Jesse packed up his things. He was ready to head back to Amsterdam early, but he turned around and came back to figure things out. The pair decided to stay together while Jesse returned to Amsterdam for work.

Ultimately, it just wasn't a good fit. Jesse met up with Darcey in New York City to end their relationship for good.

Next, Jesse appeared on 90 Day: The Single Life! He took some time to himself and focused on his job, which he traveled around the globe for. He finally felt he was ready to dive back into the dating scene.

While enjoying a traditional banya sauna experience with friends, he explained that his next stop was Colombia — to meet someone very special. Jesse had been talking to fellow 90 Day Fiance alum, Jeniffer, for a while. Although it took him a year to respond to her initial message, the two of them had an instant connection once they began chatting online.

Jesse was ready to travel to Colombia to meet Jeniffer face to face. He even left her a sweet voice note before he left for the airport. As excited as he was, Jesse worried that the chemistry he and Jeniffer had online and over the phone wouldn't be the same in person.

Jesse arrived in Colombia! He couldn't wait to start a new adventure with Jeniffer.

Jesse and Jeniffer got dressed up and and went out to dinner. Things were going well until Jesse tasted his steak and sipped the beverage he ordered. Jesse tried to focus on getting to know Jeniffer, but that was quickly overshadowed by his disappointment in his meal. Not only was the dinner not to his liking, but he was completely blown away when a dog walked right into the restaurant.

It was important for Jesse to have a strong connection with Jeniffer. So, he suggested they try out "couples yoga" together.

The next morning, Jeniffer told Jesse that her mother, Leonardi, and daughter, Violet, were coming to meet him. Jesse arrived in Colombia less than 24 hours prior and felt things were moving a little too fast. Although he was nervous, he decided to be cautiously optimistic.

However, the pressure was getting to Jesse. He began feeling overwhelmed buy the entire situation, but tried his best to have a fun day at the park with Jeniffer and Violet.

Jesse brought little Violet some fun gifts to play with. He admired Jeniffer's connection with her daughter, but he wasn't quite sure if he was ready to take on fatherhood.

Later on, Jesse and Jeniffer went paragliding! They were bonding over shared experiences, which Jesse loved.

Jesse went to dinner with Jeniffer and her cousin, Vanessa. Then, an unexpected guest arrived.

Jeniffer's friend, Cacua showed up — uninvited, of course. Jesse had no idea that Jeniffer had been dating Cacua while they were getting to know each other online and he was a bit confused about what was going on.

Jesse voiced his concerns during the car ride home. The dinner left him puzzled and he wanted to know what Jeniffer's relationship with Cacua actually was. Honesty was important to Jesse and he didn't know if he was getting the full story.

See what's next for Jesse on 90 Day: The Single Life, airing every Monday at 8/7c!

YOU MIGHT ALSO LIKE: Natalie's Journey So Far, Stephanie's Journey So Far, Jeniffer's Journey So Far

Follow TLC on Apple News