Bruce Hodgson, 38, was arrested on at a Home Depot in Pompano Beach, Fla., on Monday. He "appeared intoxicated" and was "causing a disturbance inside the store" when the store manager approached a police officer, according to Hodgson's arrest affidavit.
The officer told Hodgson to leave the property and he did, but he returned 15 minutes later.
"Again he was warned to leave or face being arrested," according to the police report. "The def. [defendant] turned around and placed his hands behind his back and stated, 'Go ahead and arrest me.'"
Hodgson was arrested and taken to the Broward Sheriff's Office main jail.
On Tuesday, Hodgson appeared before Judge John Hurley in bond court.
"Hi, Bruce, good to see you again. How ya been?" Hurley asked him. "Bruce, you didn't try to get arrested this time, did you?"
Hodgson said he was just trying to go back for another cup of coffee.
"Come on, Bruce," Hurley said. "Did it get too cold out [and] you wanted to get arrested?"
"I don't know," Hodgson replied with a laugh. Laughs can be heard throughout the room during the exchange, posted on ABC News' Miami and Fort Lauderdale affiliate WPLG's website.
On Monday, Fort Lauderdale had a high temperature of 67 degrees and a low of 44 degrees.
"Yeah, I got it," Hurley said. "When I read this this morning, I read right through this. It got too cold out there and you wanted to get arrested. Am I right?"
Hodgson chuckled and looked away before saying, "Maybe."
"See, I knew it, Bruce," said Hurley. "Well, it's good to see you again. Sorry it had to be in jail."
Hurley then asked him if we wanted to postpone the hearing until Thursday and Hodgson shrugged.
"All right, Bruce, I'll reset this for Thursday in the afternoon," Hurley said. "I think we're going to get into the 70s this weekend. Take care."
Hodgson smiled, gave him a thumbs up and walked away.
"Yeah, Bruce is a regular," Hurley said. "I can read Bruce like a book."
Hodgson has been arrested 29 times since 2000, according to the Broward Sheriff's Office.
Sixteen of those arrests took place between November and March. The most recent nine times he was arrested in the winter, the average low temperature was 52 degrees, according to WPLG.
"Certainly, we don't want to jail the homeless," Broward Sheriff's Officer Dani Moschella told ABCNews.com today. "It's not a homeless shelter, but sometimes despite our best efforts, people end up in jail because they break the law."
It costs $116 per day to house an inmate in the Broward County Jail, according to Moschella. The jail was at 85 percent capacity on Wednesday.
"The deputy's hands are kind of tied in that situation. He was breaking the law," she said. "The judge's hands were tied as well. He has someone in front of him who is cold."
Moschella said that homeless shelters are available, but they often will not take in people who are intoxicated.
Judge Hurley's judicial assistant said today that the judge cannot comment on ongoing cases, but laughed when it was pointed out to her that this is not the first time the judge has showed his sense of humor.
In February 2012, Hurley ordered a man to take his wife out to dinner and bowling, complete with flowers. The sentence came after the couple had an physical altercation when the husband forgot the wife's birthday.