Manchester United had looked at the Belgian midfielder in 2019, after an impressive loan spell at Leicester, and again in 2022, while they spent too long deciding whether Frenkie de Jong could be prised from Barcelona.
Both times, nothing materialised. It was only this July, with Tielemans away on World Cup duty, that Old Trafford finally moved, triggering a £35 million release clause to sign the 29-year-old on a five-year deal from Aston Villa.
"There had been two times that I spoke with the club, but it did not achieve anything," Tielemans recalled. "I was very calm. I was not expecting much this summer, to be fair.
"I was just focused on my football, focused on the World Cup and trying to perform my best for my country. But you know every summer something can happen, and obviously I was aware of the clause."
Conducting his first extended interview since the move, Tielemans cut a relaxed figure, personally shaking hands with every journalist in the room and breaking into a smile at several points, particularly when asked whether he can bring the same knack for big goals to Old Trafford that saw him score Leicester's 2021 FA Cup final winner and Villa's opener in their Europa League triumph over Freiburg in May.
"That's the aim," he said simply.
He was warm, too, about his old club.
"I am very thankful to Aston Villa. I owe them the world. It is a great club, we did amazing things, and they have put me back to my best level. But there are clubs above Villa, and Manchester United is one of them," Tielemans said. "It is a great achievement for any footballer to end up here. It means you have done well in your career. But it does not end there. I want to be successful."
A partnership with captain Bruno Fernandes already looks to be developing, something senior United staff noticed during the pair's brief 26 minutes together against Paris Saint-Germain in Gothenburg last weekend.
"It's really natural," Tielemans said. "He is a guy that can find space easily. I just try and find him so that he can move forward."
Tielemans also opened up on an issue that forced him out of Belgium's World Cup quarter-final against Spain, when his body suddenly gave out during the warm-up after a punishing run of fixtures.
"In that last game, it was just an overload of too many games, too many minutes. Unfortunately, my body could not cope with it any more," he explained. "We played 120 minutes against Senegal, then played the US a few days later, three days after that we played against Spain. In the warm-up, my body just switched off for some reason."
He was quick to reassure United he is not injury-prone by nature.
"I do not think I am a player that absolutely needs a rest. Obviously, there are a lot of games, and the manager needs to manage the team, but when I am good, I am good. When it does not go well, I will know straight away and I will alert the manager. But it does not happen often. I feel very good, actually."
Familiar faces have eased his settling-in period. Jonny Evans, a former Leicester team-mate who remains close to Tielemans, offered manager Michael Carrick a positive character reference before the move, while Harry Maguire also overlapped with him briefly at Leicester. Marcus Rashford, meanwhile, was a team-mate at Villa before his surprise return to his boyhood club this summer.
"He was great," Tielemans said of Rashford. "There had been so much talk about him, bringing pressure and the media around him, but he was so good. He was very humble and hard-working, and from the first training session you could tell his touch and acceleration was just amazing. That was what we needed at the time. He did many good things and hopefully he can bring them here."
Tielemans' arrival addresses a gap United have had since Carrick's own playing career ended in 2018: a scheming central midfielder capable of breaking lines and dictating tempo, potentially freeing Fernandes to play further forward. Having had only a brief chat with Carrick before completing the move, Tielemans says the past ten days of pre-season have given him a clear sense of what his new manager wants.
"He wants me to be free on the pitch, to try and organise the team the best I can," he said. "He has got his structure. He wants to have the ball and wants to press in certain ways. It might be different than what I am used to, but it is logical things in my opinion. It is just smelling football, which is what I have been doing from when I was young at Anderlecht, you know. For me, nothing changes, but it just needs to gel together."