TikTok's Apartment Tour Guy, Caleb Simpson, Reveals He's Newly Single During Surprise Appearance at Live Dating Show
TikTok star Caleb Simpson just revealed he’s newly single.
The 33-year-old social media star has over 8.5 million followers on TikTok and he’s known for asking people how much they pay for rent, and then having them giving tours of their apartments. His most recent videos featured Shark Tank‘s Barbara Corcoran and SNL‘s Chloe Fineman.
Caleb made a surprise appearance on the latest episode of the YouTube dating show UpDating and revealed he’s newly single.
“I am single as of four days ago,” Caleb said on stage.
The episode was seemingly taped on May 22 in Brooklyn, N.Y. according to the event listing, which puts the breakup on May 18. Caleb was most recently linked to a famous Broadway actress.
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Caleb started dating actress McKenzie Kurtz in 2023 and they seemingly just broke up. While they don’t share regular posts together on social media, they last attended a public event with each other in February 2025.
For those who don’t know, McKenzie made her Broadway debut in 2020 while playing Anna in Frozen and she later played Glinda in Wicked and originated Cassandra Stone in The Heart of Rock and Roll. She’ll soon be seen in the off-Broadway return of Heathers: The Musical.
When asked if he’s doing okay, Caleb told the UpDating hosts, “Yeah, I mean, I’m here. So I’m doing alright.”
UpDating is a dating reality and comedy show where two single people are set up on a blind date in front of a live audience. The contestants are blindfolded and have to decide if they like the other person before taking the blindfold off.
Caleb was brought on stage as a possible suitor after a couple was already formed. He was asked if he’s interested in going on a date with Becca, the contestant, and he said, “It’s a thumbs down for me.” When she took off her blindfold, Becca was unbothered and said, “It’s okay, you’re not my type.”
Becca also had no clue who Caleb was as she thought he was a real estate agent from all of the apartment talk and said she’s in the market for one.
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