Saturday was an exceptionally long day for Bobby Brown.
The singer appeared at his ex-wife Whitney Houston’s funeral for a short time early in the day. Later, he took a private jet from New Jersey to Connecticut to perform at the Mohegan Sun casino’s arena with his longtime, on-and-off band New Edition, according to a rep for the casino.
The show – which lasted more than an hour and included hits such as “Candy Girl,” “Mr. Telephone Man,” “Tenderoni” and “My Prerogative” – featured some emotional moments for Brown.
“I wanna give blessings to my ex-wife Whitney Houston. I love you,” Brown said, pointing toward the sky. “I want to give blessings to my kids, my brothers and all of you. Thank you for the love.”
“He was upset today,” one of Brown’s band mates told the crowd, adding that the rest of group told him, “hit ’em with your voice, man.”
After the show, Brown, some band mates, and a group of family and friends hit Bobby Flay’s restaurant Bar Americain. Wearing a gray vest and a Red Sox baseball cap, Brown looked relaxed and low key as he posed for photos with fans. A source tells PEOPLE he drank Grey Goose on the rocks. At one point, he did a little dance for the table.
Brown hugged friends and family throughout the evening, as the crowd of about 15-20 people hung at the upscale bar and restaurant along with him.
Around 12:15 a.m, he and much of his entourage left the restaurant and headed for the high rollers gambling area of the casino, where Brown settled into a $500 minimum bet blackjack table.
“He wasn’t really partying, but he was having a good time with his old crew from Boston,” says an onlooker. “He had a lot of support and bodyguards stuck close to him to keep fans from being too intrusive.”
But Brown and friends gambled for only a short time. Says an eyewitness: “In the end, it looked like his heart wasn’t in it. No one gambles for 20 minutes. It was like token gambling just because they were there at the casino.”
They soon moved on as an entourage across the casino floor, where Brown posed for more fan photos. He was holding his fiancée, Alicia Ethridge’s hand much of the time. Around 1 a.m., they arrived at seafood joint and raw bar Summer Shack and hunkered down at a secluded back table. There, Brown seemed to really crash, putting his head down wearily at times.
After a quiet snack, smokes and drinks, a source tells PEOPLE, they all filed out at 2 a.m. and back to their hotel rooms.