Chloe leaves Boston for Aruba but trust is already wobbling- 90 Day Fiance S7 E2

Chloe makes the leap from Boston to Aruba, leaving behind not only her mother and financial stability but also the structured lifestyle she has always relied on. At 23, she is still figuring out her future, and yet she is willing to move across the world for Jonathan. She admits she doesn’t do well without a plan or routine, and this move strips her of both. Her mom, Michelle, voices concerns as they pack—worried about Teddy the family dog, Chloe’s financial future, and her safety abroad. Chloe reassures her mom but privately admits she doesn’t truly know what will happen once she lands in Aruba.

Jonathan’s world: fun, tips… and built-in temptation

On Aruba, Jonathan (Johny) introduces viewers to his daily life on the Jolly Pirates cruise. As first mate and MC, he entertains tourists with flips, acrobatics, and constant crowd interaction. The atmosphere is alcohol-soaked and flirtatious, with women seeking out locals during vacation. Jonathan openly acknowledges that temptation comes with the job—tourists throw attention his way, and he can’t be rude because his income depends on tips. He insists he tries to keep boundaries now that he has Chloe, but the reality is that the setting itself fuels her jealousy.

The trust problem (and it’s two-sided)

Trust issues dominate their storyline. Jonathan admits that at the start of their relationship he wasn’t exclusive and made “dumb” choices. Later, while Chloe slept, he went through her phone and discovered sexual conversations with another man. When confronted, Chloe denied wrongdoing, but Jonathan felt she was lying. Both admit to mistakes, and though they agreed to exclusivity, their history makes it hard to believe one another. This mutual lack of trust sets the stage for nearly every argument between them.

The jealousy loop: calls, cameras, and location sharing

To reassure Chloe, Jonathan has gone to extremes: sharing his location, giving her access to cameras around his home, and trying to answer calls any time of day. But this constant monitoring has created more conflict than peace. For example, when Jonathan sat outside on his patio where one camera couldn’t see him, Chloe assumed he had left for hours. Despite his explanations and evidence that his car never moved, the argument dragged on for days. Jonathan admits the cycle is exhausting, but he feels stuck between protecting his job’s tipping culture and easing Chloe’s insecurities.

What Jonathan says he wants

At 32, Jonathan insists he is ready for stability and family life. He says he has “partied more than enough” and now dreams of a long-term partnership and eventually marriage. He even hints at proposing if Chloe proves she’s ready for commitment. But he worries that Chloe, nearly a decade younger, may still crave the carefree lifestyle. He fears she sees Aruba as a paradise where friends visit, drinks flow, and responsibilities fade. He wants to slow down; he’s not sure she’s ready to give up the party.

Chloe’s side: goodbye Boston, hello unknowns

Chloe’s final hours in Boston capture her inner conflict. She hugs Teddy, jokes with her mom about his age in “dog years,” and drags her luggage downstairs. She says she’s thrilled to reunite with Jonathan but admits she’s terrified of leaving her job security, friends, and family. Chloe describes herself as a structured person who thrives on routine, and she knows moving without work or clear plans is risky. Yet, she compares herself to the cheerleader who always had to trust being thrown into the air—taking a leap and hoping not to fall.

What Mom doesn’t know

Michelle has her concerns but doesn’t know the full story. Chloe hides Jonathan’s past infidelity from her, afraid it would permanently damage her mom’s view of him and their relationship. By keeping this secret, Chloe places more pressure on herself to prove the move isn’t a mistake. She frames the relocation as a love story, not a gamble, but the unspoken baggage lingers.

Stakes heading into the reunion

• Jonathan’s job risk: He works daily in an environment where alcohol and flirtation fuel income, testing Chloe’s patience.
• Mutual mistrust: Both have cheated or crossed boundaries in the past, and neither fully trusts the other.
• Different life stages: At 32, Jonathan wants marriage and family; at 23, Chloe may not be done with nightlife and freedom.
• Structure vs. spontaneity: Chloe thrives on plans; this move leaves her winging it, something she admits she struggles with.
• Constant surveillance: Cameras, calls, and location-sharing keep tensions high rather than building trust.

The episode leaves them here

The S7E2 episode of 90 Day Fiancé: The Other Way ends with Chloe boarding her flight, nervous but determined. Jonathan continues his shifts on the party boat, reminding viewers he’s ready to settle if Chloe shows the same commitment. Their reunion is just days away, but with jealousy, secrecy, and lifestyle differences already weighing on them, the big question looms: can this couple build trust in Aruba, or will Jonathan’s pirate-ship world and Chloe’s need for structure clash beyond repair?