Serena is an Editor with Screen Rant. She has expert knowledge of all things 90 Day Fiancé, and has a deep love for reality TV in general. Her other top shows include Below Deck, Married at First Sight, Love Is Blind, Love After Lockup, The Traitors, and several Real Housewives franchises  She has been a reality TV fan since the early days of Survivior and Bad Girls Club.

These shows are comprised of franchise cast members in new chapters of their lives. Currently, there is a brand-new spinoff in the network. 90 Day: Hunt For Love follows former cast members who are now single, as they enjoy a Tulum, Mexico, resort while trying to date each other and strangers, all while getting help with their dating skills. Exes Tim Malcolm and Jeniffer Tarazona, who had a 13-year age gap relationship, have been taking center stage as their tension is palpable and Jeniffer tries to sabotage Tim’s experience.

While Tim and Jeniffer’s relationship was notably problematic, there are other franchise cast members whose age gap relationships are even more toxic. The messy nature of the age gap connections on this list have been shocking, distasteful, and downright weird at times. There are some couples like 65-year-old Jenny Slaten and 35-year-old Sumit Singh who’ve proven age disparities can work, but the ones that don’t work are more glaring.

8 Gino Palazzolo & Jasmine Pineda

Jasmine Had Another Man’s Child

At the couples therapy resort, Jasmine said she and Gino had not been intimate for nine months, and that she wanted an open marriage. To avoid conflict, Gino agreed. However, Jasmine became pregnant with her partner in the open marriage, Matt Branis, and she has since given birth to their daughter. The other layer of their relationship involves Jasmine’s financial dependence on Gino, who Jasmine thinks tries to control her with money. Despite being closer to senior status, Gino has underscored his bad decision-making, and younger Jasmine is taking advantage.

7 Mark Bessett & Mina Mack

Mark’s Family Doesn’t Trust Mina

59-year-old Pilot Mark Besette met 34-year-old Mina Mack allegedly at a restaurant in Paris, although there are rumors suggesting that Mina was a stripper, and they met in the club she worked at. In any case, Mina already had a child from another partner, and she and Mark shared a two-year-old, Maria, together. And Mina wanted more kids. Mark’s grown daughter, Jordan, felt her dad was making a mistake with Mina, and that Mina was using him for his money and lifestyle.

6 Tigerlily Taylor & Adnan Abdelfattah

They Married The Same Day They Met

Tigerlily Taylor, 41, met Adnan Abdelfattah, 22, on social media, and the pair were only talking for four months before Tigerlily flew to Adnan’s native Jordan to meet him. Throwing all caution to the wind, middle-aged double divorcee Tigerlily married Adnan the same day she arrived in Jordan. She didn’t even know that he wanted five kids or that she would need to present herself a certain way to appease Adnan and his Muslim culture.

5 Big Ed Brown & Liz Woods

Big Ed Likes Younger Women

Before the now-60-year-old Big Ed Brown met now-32-year-old Liz Woods, he flew to the Philippines to meet his online girlfriend, Rosemarie Vega, who was only 23 to Big Ed’s 54 on Before the 90 Days season 4. Big Ed has always said that he prefers younger women because he feels young at heart. However, Big Ed’s penchant for younger, vulnerable women has largely come off as concerning and gross.

4 Molly Hopkins & Luis Mendoza

Luis Left Molly

3 Rebecca Parrott & Zied Hakimi

Rebecca Spied On Zied

Rebecca Parrot has a 22-year age gap with her Moroccan husband, Zied Hakimi. Not only did Rebecca catfish Zied, but she had also brought over another Moroccan man on the K-1 visa before Zied, which presented double red flags. However, Rebecca and Zied are still together today, but Rebecca is still not acting her age. In 90 Day Diaries, Rebecca followed Zied to a bar and incorrectly accused him of cheating on her. Despite being the older one in the couple, Rebecca is more immature than Zied, and she causes her own issues.

2 Ben Rathbun & Mahogany Roca

Ben Has Passed

Ben Rathbun was 52 years old when he met 22-year-old Mahogany Roca online. Despite being a religious father of four, Ben went down to Mahogany’s native Peru to pursue her. She gave him mixed signals, but Ben was relentless in his pursuit of Mahogany. They did end up getting married, and Mahogany seems to have moved to the U.S. Sadly, Ben passed away in May 2025, leaving Mahogany a widow