OSWEGO – The only thing this ex-DoorDasher is delivering is a struggle meal.
The disgraced driver who was fired, and then charged after she posted a TikTok video of a customer half-naked inside his own apartment was spotted with a bag of chips and a frozen dinner while free on bail.
Olivia Henderson, 23, sported a frumpy ensemble of boot-cut jeans, an oversized hoodie and white sneakers – with the shoelaces untied – while running errands.
Henderson was spotted with a bag of chips and a frozen dinner while free on bail. NYPJ for NY PostHenderson made a run to Walgreens, Kinney Drugs and Price Chopper, where she bought dinner.
Up until 2024, Henderson — a former student at FIT in New York City — was a vibrant presence on Facebook, regularly showcasing an eccentric aesthetic defined by Lady Gaga-inspired hair, fashion, and makeup.
Last October, Henderson arrived at a customer’s apartment to deliver a Wendy’s order, where she saw a man passed out partially naked on his couch through his door and recorded him with her phone — posting the video to TikTok, police said.
She claimed she was being sexually harassed because his pants were around his ankles.
Following a police investigation – which included footage of the naked man, who said he had passed out drunk and forgot he ordered food – Henderson was arrested. She made her first court appearance in December 2025.
Last Friday, a grand jury indicted her on two felony counts: unlawful surveillance and Dissemination of an Unlawful Surveillance Image. She pleaded not guilty.
Olivia Henderson, a former DoorDash employee, posted a video of a man nude in his home while delivering his food. TikTok/@irlmonsterhighdollHenderson’s Attorney, David Smallwood, told the Post “the plan is to figure out what the DA wants to do about this.”
“It’s definitely a lot bigger than it should be.”
The 27-year-old alleged victim said in a deposition acquired by the Post that he felt “unsafe, humiliated and upset,” because Henderson not only posted the video footage, but also disclosed his first name and house number in the clip.
She is scheduled to return to court for further proceedings as her defense and the prosecution discuss a potential plea deal, according to ABC7.
If convicted of both felony counts Henderson faces up to eight years in prison.
