Peering out from behind the 15ft-high solid oak door Prince Andrew is seen to catch himself and check if anyone is watching as he waves goodbye to an attractive brunette.
And it may be little surprise that he was concerned that someone might spot him in the doorway of the £63million Manhattan mansion, as it belonged to convicted paedophile Jeffrey Epstein.
A video of the encounter emerged as the Duke of York faced a growing list of questions over this association with the financier who died in prison in an apparent suicide earlier this month.
The Duke is seen in the video emerging in the imposing doorway of the New York building which Epstein’s victims have dubbed the “House of Horrors” to chat for a few seconds and then wave goodbye to an unnamed woman.
Before he closes the door he peers around it apparently to see if anyone is watching.
Less than an hour earlier Epstein had left the house in a thick fur-lined coat in the company of a young blonde woman who was wearing a thin jumper and appeared to be shivering.
Witnesses told the Mail on Sunday that the woman entering and leaving the house whilst the Duke was inside “looked very young indeed”.
The footage is from December 2010 when the Duke, then the UKs Special Representative for Trade, stayed with Epstein in his New York home.
Previously pictures have emerged from the same trip of the pair walking together in Central Park.
The corridor in which the Duke stood to wave goodbye to the woman is said to contain a number of bizarre items, including a painting of Bill Clinton wearing the dress Monika Lewinsky was infamously wearing when she performed a sex act on him and a chandelier with a life sized female doll hanging from it.
Two years before the video was shot Epstein had been convicted of sex with a child and placed on the sex offenders register.
The emergence of the video came after prosecutors in the US said they were continuing their investigations into Epstein's crimes and their attention had turned to his associates.
The source said that they had gone public with the footage to try and encourage other victims to come forward.
The Duke is braced for the release of further court documents in coming weeks after being named in documents relating to British socialite Ghislaine Maxwell, who is alleged to have “acted as a madam" for her lover Epstein. She has repeatedly denied the claims.
Buckingham Palace have refused to comment on the video but have recently repeated their “emphatic denial” of allegations against the Duke made by Virginia Roberts, one of Epstein’s victims.
A spokesman for the Palace said: “Any suggestion of impropriety with underage minors is categorically untrue.”
The Duke is currently on holiday in Spain with his ex-wife Sarah Ferguson.
The Metropolitan Police have refused to say whether they will look at requests by Ms Roberts to resume their inquiries into the allegations she made surrounding her time in London.
In 2015 Detectives looked at allegations that Ms Roberts, who now uses her married name Guiffre, was trafficked to London for sexual exploitation but they did not to pursue a full investigation.