The victims were robbed in separate incidents in Yardley, east Birmingham, after being contacted for potential dates, West Midlands Police said.
Two of the attacks took place off Yardley Green Road, on 5 January and 18 March, while the third took place off Hob Moor Road on 24 March.
On Thursday, officers arrested two 17-year-old boys and a 16-year-old boy from the Bordesley Green area on suspicion of robbery.
One of the 17-year-olds was charged and remanded to appear at Birmingham Magistrates’ Court on Saturday.
Officers arrested another two teenagers on Friday on suspicion of involvement in the attacks, bringing the total number of arrests to five.
The boys, aged 17 and 18, were questioned by detectives and the 17-year-old was charged with one count of robbery.
He has been remanded to appear at Birmingham Magistrates’ Court on Monday at 10am.
The other three teenagers have been released on police bail with strict conditions.
The Birmingham arrests come after a 21-year-old man was arrested in connection with attacks in Manchester on three other men who had also arranged meetings through Grindr.
David Aroge, of Holden Drive, Swinton, was charged with three counts of robbery, three counts of possession of a bladed article and one count of assault in connection with the incidents.
The three victims were attacked within a 24-hour period by a man they had been matched with on the dating app. Each attack became more violent, police said.
Chief Inspector Amanda Delamore, of Greater Manchester Police, said: “Our thoughts remain with the three victims who have all been left incredibly shaken by their ordeals and officers will continue to provide them with support at this distressing time.
“Our investigation does not stop here and I would continue to urge anyone with any information that could assist us to please get in touch with police.”
West Midlands Police have advised anyone planning to meet someone from a dating app to meet in a well-populated area.