Dempsey will play his 50th Test on Saturday – he has 14 for the Wallabies and this will be number 36 for Scotland.
His life is different now.
Based in Japan, he’s available for all of the Nations Championship, unavailable for all of the Six Nations and then available again for the World Cup. That move to Japan, after five years with Glasgow, was one he thought about long and hard.
His mind was ever-changing when he was weighing it up, he says. He admits to feeling a little guilt over leaving the club that “resurrected” his career. Then there was the prospect of missing the Six Nations.
“You can be playing the Six Nations and be like ‘this is the greatest thing, winning a Calcutta Cup’,” he says. “All the other games as well, but mainly that one. You’re like ‘I’d love to drink from this cup every single year for the rest of my life’.
“I’d wake up one day and change my mind, wake up the next day and change it again. For me, it just came down to the cliche of only having one career. Let’s try and do as much as you can.
“I’ve been so lucky to play Super Rugby, played for my home country, played for Glasgow and then played at Murrayfield. One thing I’ve learned in my career is that Murrayfield is the best place to play rugby, without a doubt.
“Every time you go to Murrayfield and play a game it’s like it’s your first one. You want to make sure that you don’t take that for granted.”