Their First Date Ended With a 5-Year Prison Sentence

It should be a happy Valentine's Day if you can avoid a date like this: A Rhode Island man was sentenced to five years in prison Tuesday in connection with a 2016 bank robbery he committed while on a first date with a woman who unwittingly acted as his getaway driver. The Massachusetts woman, who met Christopher Castillo on a dating app before picking him up at his parents' house on Dec. 5, 2016, didn't think much of his request to stop at a bank once they got to her hometown of Attleboro Falls, even after he'd downed wine in the passenger seat in the middle of the afternoon. That is, until he came sprinting back to the car with a .44 caliber gun and $1,000 in cash and told her to "f---ing go," per CNN and the Washington Post.

Panicking, the 40-year-old driver took off but pulled over once officers began tailing them. She was initially charged with being an accessory after the fact, per the Attleboro Sun Chronicle. She was held on $250,000 bail before the charges were dropped, leaving her with the ultimate bad date story. But the trouble was just starting for Castillo, who'd showed his stepfather's antique gun to a teller at Bristol County Savings Bank, complaining that he was "really hurting," per the Post. The 33-year-old was sentenced to three years for armed robbery and two years for assaulting three police officers. He had to be removed from the car in a violent struggle and spat on cops, per WHDH. (This disastrous first date also involved wine.)