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The Season 2 storyline: Jesse, Cacua, and a trip to Colombia
Jeniffer’s Season 2 arc began with the end of her relationship with Tim Malcolm. According to TLC’s retrospective on her journey, she and Tim had met through a Colombian dating website, and their storyline ended before the new season’s romance took shape. TLC’s retrospective on Jeniffer’s journey is the most detailed account of what followed.
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That account says Jeniffer was talking online with Jesse, whom she had messaged, and that he responded about a year later. At the same time, she was seeing Cacua, a longtime friend in Colombia. Jesse traveled to Colombia, and the overlapping relationships, along with the question of what Jeniffer had told Jesse about Cacua, became a source of conflict in the new relationship.
The season presented this as a developing romance rather than a settled outcome. Jeniffer’s own words from a November 5, 2021 Us Weekly preview capture the mood at the time. She said, “I feel like a schoolgirl again,” in a passage describing her nerves and excitement about the relationship. Us Weekly’s preview is the contemporary source for that quote.
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Why the relationship with Jesse ended
The relationship did not survive the distance. TV Insider’s profile of Jeniffer dates her announcement of the split to September 2022 and identifies the gap between Jesse’s base in Europe and her life in Colombia as the difficulty they could not bridge. The profile summarizes the outcome of the Season 2 story; it does not describe the private conversations that led to the decision, and readers should not treat it as a fuller account than that.
The 2025 return on Hunt for Love and Cole Anderson
Jeniffer came back to the franchise in 2025 on Hunt for Love, where she chose Cole Anderson at the finale and left the resort with him. TV Insider’s September 2, 2025 report said the two were still together at the Tell All, which was filmed in June 2025. The same report said neither had publicly commented on their relationship after the Tell All.
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That report is the most recent relationship-status evidence available for Jeniffer. It describes the couple at a specific point in 2025, not at any later date.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What is and is not established as of October 8, 2026
- Established: Jeniffer’s Season 2 romance with Jesse Meester ended, with the split announced in September 2022 according to TV Insider.
- Established: Jeniffer returned in Hunt for Love in 2025 and left with Cole Anderson.
- Established as of June 2025: She and Cole were reported together at the Tell All filmed that month.
- Not established: Whether Jeniffer and Cole are still together in October 2026. The sources reviewed do not include a dated update after September 2, 2025, so the 2025 report should not be read as a current status.
Where to watch
The September 2025 coverage lists Hunt for Love as streaming on HBO Max. Streaming libraries change, so confirm availability on the service before you watch. The Season 2 episodes featuring Jesse and Cacua are the source material for the storyline described above.
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