The Dutchman has always erred on the side of 'luxury player' and the lack of possession and the frequent relegation scraps in the Bundesliga were beginning to weigh him down.
All the 32-year-old’s ever wanted to do is have fun playing football; without that enjoyment, he threatens, he would quit the game.
During those protracted, dim winter nights in Germany, he allowed his mind to wander to a time when he was relishing his profession.
"I always used to go the The Live Room in Barnet with Robbie Keane [after Tottenham matches], I still have photos from there actually," he says, laughing, as he remembers pulling pints at Keane's leaving bash.
Rafael van der Vaart's career in pictures
"I've never been back there actually. I've been to London a few times, but you end up in a hotel in the centre."
Van der Vaart has just signed for La Liga side Real Betis following a career which has taken in Ajax, Hamburg, Real Madrid and Tottenham.
He was still living on a caravan park with his family when he made his debut as a 17-year-old for Ajax, a club he won two Eredivisie titles with, and he was presented at the Bernabeu in front of 20,000 frenzied Madrid supporters.
He's been capped over 100 times by Holland and he played in the 2010 World Cup final, but it's those evenings in The Live Room and his two years at White Hart Lane where his memory is often drawn.
"Because I didn't have a contract [this summer] I almost tried to come back [to Spurs], then Betis came and I decided to come to Betis, but Tottenham was always special," he tells Mirror Football at the Seville-based club's Luis del Sol training ground.
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The two years Van der Vaart spent in North London, he is all too keen to offer, were the best of his career. It begs the question, why did he leave?
"It was a little to do with everything," he continues in the 40 degree heat gripping the south of Spain.
"It was private things, but also when what's his name [Andre Villas-Boas] came he said to me 'you're not my number one' and I had played two years, like, unbelievable, so for me it was really strange that he said that to me. So then I said, well, it's better to leave and that is what happened.
"It was a stupid decision, the most stupid in my career to leave Tottenham. I absolutely regret it because it was the best two years in my football life.
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"And Harry [Redknapp] — he was like your dad. I would give everything for that man; I was really sad when he left. I think the England job would have been the best job for him and also for England."
Shortly after his Real Betis unveiling, where he was presented alongside his Spanish grandma, Dolores, who lives 80 miles south of Seville, an article in another national newspaper put it that his his choosy, shirt-out swagger and brio has too often been a square peg in a round hole.
"I don't think so," he replies when this is put to him. "Football changes, of course, you see it everywhere. The typical No.10, maybe there are only a few left because the majority of teams don't play with a No.10.
Alexander Hassenstein
"No.10 was always my best position, but I think now I could also play [this season] like a No.6, in front [of the defence] and build the play from deeper."
Van der Vaart turned down offers from Ajax and MLS side Kansas City to sign for Real Betis, citing a three-year deal as the clincher.
However, he also deemed La Liga a good home because he's anxious to be part of the Holland squad which he hopes will form part of next summer's 24-team European Championships in France.
There can be no doubts that he feels ready to take on the challenge in a country where he fills his skill-set best acclimatises, but nagging doubts persist over whether he’s really accomplished as much in his career as he perhaps should or could have.
After three unsatisfying years at Hamburg, he’s at least hoping that under Betis’ attacking boss Pepe Mel he can extract some joy from the game once again — just like he did at Tottenham.
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