Wimbledon semi-finals. And how to avoid losing them. Four times he made it to this stage – 1998, 1999, 2001 and 2002 – without ever being able to take that agonising final step. He bears all this with incredible good grace, particularly an inquiry as to whether semi-finals are the most excruciating matches of all. "If I had played a final then maybe I would be able to answer that question," he deadpans, before his expression dissolves into a smile.
As part of the BBC commentary team, Henman is as accomplished a performer in the media these days as he was when the No.4 tennis player in the world. His neutrality is, however, perhaps fatally compromised by the closeness of his friendship with Andy Murray, an alliance which began when he was the elder statesman and Murray was a raw, gangly kid making his first steps into the Great Britain Davis Cup team. In any case, all this backstory marks him out as an expert witness when it comes to Murray equalling his own Wimbledon record and going into his fourth semi-final at SW19 against Jo-Wilfried Tsonga on Centre Court this afternoon.
For the record, Henman says he feels dealing with these semi-finals got easier as he went along and fully expects the Scot to prevail at this stage at the fourth time of asking to become the first British male singles finalist at Wimbledon since Bunny Austin in 1938.
"I look back on them [my semi-finals] with massive pride," said Henman, who reached the semi-finals at every major apart from the Australian Open. "I would have loved to have gone further but I still loved every minute of it. I can look back at the [Goran] Ivanesivic match in 2001 and say it was my best opportunity, but we all know the history of that match and it wasn't meant to be.
"The aftermath of them didn't get any easier, it probably got worse," he added. "But in terms of the preparation and going through the whole journey in the tournament, if anything it got easier. I felt I was a better player and I felt I was more experienced. I have really enjoyed sitting and watching these scenarios unfold with Andy, having been through this process myself. I do think he is better equipped to go further. He is a better player than I ever was."
A strange sort of hysteria takes hold when any British player reaches the last four at SW19, and Henman feels Murray is adept at insulating himself from it all, as he was. The first time he used to see the numerous front and back pages he had generated – not all of them flattering – was when they got brought out at his parents' Oxfordshire home for Christmas dinner.
"I was flicking through newspapers this morning and it would be terrifying for him to sit down and read it all," Henman said. "But I can say hand on heart than when I was in the middle of it the only expectation was from within. I couldn't wait to be out there playing.
"I always remember the funny front pages in some of the tabloids and the front pages of broadsheets or whatever – my parents would keep some of the funny ones and I would see them at Christmas," he added. "I'd sit down and look at them for half an hour and it was brilliant. Sometimes the press gets quite a lot of criticism – and quite rightly so – but for me to take myself out of it and look at it over the new year and see some of the stuff, it was brilliant. You still pinch yourself and think: 'Wow, was that really all about me?' I really hope Andy is enjoying it. I think he is."
Murray, of course, still has a mountain to climb if he is to emulate Fred Perry's 1936 victory here. Henman rates Novak Djokovic as the outright favourite and there is no doubt that Tsonga, the Muhammad Ali lookalike from Le Mans, is a heavyweight semi-final opponent. The BBC pundit feels the 5-1 head-to-head advantage which the Scot has over the world No.6 is deceptive and is particularly wary of the performance the Frenchman put on against Djokovic at Roland Garros last month which took him all the way to match point. None the less he expects the 25-year-old from Dunblane, with the laughably undemonstrative Ivan Lendl in his team, to have the measure of the Frenchman this afternoon.
"When you have someone in your corner who has been to 20 grand slam finals, and who lost his first four, just that voice of wisdom and reassurance for Andy will be great to have," Henman said. "But the head-to-heads mean little when you actually step out on the court because Tsonga is so dangerous. One of the performances I would be most wary of was at the French, because to play that well against Djokovic and get that close shows that you can really do some damage. But Andy's athletic ability is incredible and the way he is able to get serves back and stay in rallies, I think that will frustrate Tsonga. He has got a huge serve and a huge forehand but I think Andy will be able to get after his backhand.
"I commentated on a couple of Djokovic's matches and he has looked in awesome form," the 37-year-old added. "With the conditions the way they are, his athletic ability and the way he plays off the ground, he's the favourite for the tournament. We can talk about Murray with this semi-final and potentially getting to the final, but I think Djokovic is the favourite."
The Scot is second on Centre Court this afternoon, as Henman so often used to be, to coax viewers into the BBC's early evening schedule. But unlike those rain delays which frustrated Henman against Ivanisevic, there is a roof these days, even if he admits that the All England club's schedulers have found it "quite tricky this year". "I loved playing second, the last match on centre and that atmosphere – get the ratings up! It was brilliant. With hindsight, I would have loved to have played first in 2001, but I think second on centre is the way forward."
He will speak briefly to the man who is attempting to follow in his footsteps today before strolling over to the gantry and picking up the microphone. His last words will be delivered as a friend and confidant, rather than as an impartial observer or critic. "I will go and see him beforehand and wish him good luck," Henman said. "I have chatted to him a bit, but he has his team around him and I speak to him as a friend, not someone wanting to give input. I know what it is like on the other side of the fence. There are so many opinions coming in, the last thing you want is another one."