Picking up the 30-year-old man from his parents' place might have been a red flag and so might the fact that he started to drink wine in the passenger seat, but a US woman had no idea that her first date could turn out as badly as it did.
40-year-old Shelby Sampson from Massachusetts had met Christopher Castillo on a dating app and the pair had never met in person when she picked him up from his family home in Rhode Island in December 2016.
CNN reported he proceeded to drink wine in the passenger seat, asking her to take him to a bank 30 minutes away, across state lines in Massachusetts.
So far, so weird.
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But when he returned to the car after a few minutes he was sporting sunglasses and a hat and holding US$1000 (NZ$1552) in cash and a gun.
"F***ing go," he told her.
Sampson would later tell police that she "panicked" when he returned to the car.
Court documents reveal that Castillo walked into the Bristol County Savings Bank in North Attleboro and told a bank teller he was "really hurting", producing a gun and demanding the money, saying he badly needed it.
After the new couple made their escape, Sampson noticed that they were being followed and eventually pulled over and walked away from the car.
Court documents reveal that policed pulled Castillo out of the car as he "violently struggled", spitting on the officers and telling them that the gun wasn't loaded.
After he was brought under control, a search of the revealed an antique handgun and Castillo's basic disguise.
The money was found in his wallet.
Both Castillo and his date were arrested at the scene but once investigators heard her story she faced no charges.
Castillo pleaded guilty this week to armed robbery and assault and battery on a police officer.
He was sentenced to five years, three for the robbery and two for his assaults on police.