90 Day Fiance star Libby’s sister, Jenn, has some spicy skeletons in her own closet! She had a shocking relationship in the past as she dated a super-famous man. While Jenn is making headlines with none other than Natalie’s ex-boyfriend, Josh, her past is leaving viewers in disbelief now.

But that’s not all. There is a lot more to the story, as Jenn’s past is turning many heads now. Is this true? What is this all about? Who is Jenn’s former boyfriend? You surely are willing to get every bit of this tea! So, keep on reading to learn more about this headline because these facts will leave you in disbelief.

90 Day Fiance: Jenn & Josh Are Together Exploring The Dating World

90 Day Fiance star Josh Weinstein openly admitted that he was seeing someone else after dumping Natalie. Apparently, he was dating none other than Libby’s sister, Jenn. Josh revealed that he had known the latter’s family for several years, and they had been connected for a while now. He appeared to be really happy with Jenn while he was actually planning a few trips with her.

However, Josh and Jenn didn’t seem to be sure about their future. They believe that they are still figuring out the dynamics while they were having fun together. Jenn admitted that Josh was making her happy, and she was able to form a bond with him. Hence, viewers are now willing to see where this storyline will go!

90 Day Fiance: Jen Dated Famous Orlando In The Past

Eversince Jenn and Josh made their relationship official on 90 Day Fiance, viewers have been digging into the former’s past. A Reddit thread recently shared a picture of Jenn with her former boyfriend. The OP revealed that the noted celeb dated none other than Orlando from “Orlando and the Freak Show.”

Yes, you read that right! Jenn’s former boyfriend was the host of Orlando and the Freak Show. Fans were in disbelief after learning that Libby’s sister had actually dated someone really famous. The OP further shared a picture of Jenn and Orlando, where they happily stood together and grinned at the camera.

The OP further noted, “I’m trippin!!! Wonder what their relationship was/is like… I’m fascinated.” However, some viewers believe that Jen was only with Orlando because of his money. A user noted, “It seems like he had loads of money and I’m pretty sure that’s why she was with him.” Another one added, “He does look her type. In that he has money.”

But that’s not all. Some fans claimed that Josh wasn’t an upgrade, and Orlando was a wonderful person. They further wondered how Jen dated him because she allegedly appeared to be a “racist.” A fan noted, “Im surprised she was with a Black guy when she herself seems very racist vibes.” What do you think? Do let us know in the comments section.