Option one: he’s sitting in the Murrayfield stand supping Guinness, just as he was last year when Gregor Townsend’s side edged out the Wallabies 15-13 in a thriller best remembered for Ewan Ashman's stunning try.
Option two: he’s pulling on the gold and green for the first time in three years and winning his 15th cap for the country of his birth.
Option three, and here’s where it gets interesting: Dempsey takes advantage of World Rugby’s new rule on eligibility which allows capped players to transfer allegiance as long as they have spent the previous three years out of the international game and have “a close and credible link via birthright” to the country to which they are switching.
Dempsey’s Scottish link is through his grandfather on his mother’s side and you suspect there will be much to discuss when the player’s parents visit Scotland later this month.
Dempsey is coy when asked if he's spoken to Townsend about switching sides.
“Maybe I have or maybe I haven’t,” he smiles. “I don’t know. I can’t really talk about it.
“I’m pretty focussed on the Warriors at the moment. I’m going to have a deep think.”
What is not in doubt is the impact Dempsey has had at Glasgow this season. The Sydney-born back-rower has added a hard-running, abrasive edge to the Warriors pack, helping them through to the quarter-finals of both the URC and the Challenge Cup.
Would it benefit Scotland? Absolutely. Townsend already has high quality No 8s at his disposal in the shape of Dempsey’s Glasgow team-mate Matt Fagerson and Bristol-bound Magnus Bradbury but more competition can only be healthy.
Dempsey last played for Australia on October 11, 2019 so would become eligible for Scotland 18 days before the Wallabies visit Murrayfield. Publicly at least, he says he’s focusing solely on club matters at the moment.
“A few of the lads have been into me, trying to get some insight into what I am thinking,” he said.
“But I’ve pretty much had the same mindset since the laws were changed back in December or January, or whenever it was. I’m just focusing on the Warriors at the moment and, obviously, the date for me to officially change isn’t until September or October or something like that, so I’ll address that when the time comes.
“There’s no point thinking about it too much now, especially when we’ve got such big games coming up.
“We’re missing a few key guys in our squad at the moment who we are hoping to get back, but I’m just focusing on doing my role and making sure that I can stay on the pitch and play well for the Warriors.”
Glasgow head to France on Friday for Saturday’s Challenge Cup last-eight tie against Lyon, a tough test for Danny Wilson’s depleted squad who will go into the game without the injured Rory Darge, Tom Gordon, Fraser Brown, Matt Fagerson, Scott Cummings, Kyle Steyn, Seb Cancelliere, George Horne and Rufus McLean. Stand-off Duncan Weir is also a doubt.
The Warriors have struggled on the road this season but they secured an impressive win at Newcastle in the last 16 and will look to senior players such as Dempsey to lead the way in Lyon.
An experienced campaigner, the No 8 played for Australia at the 2019 Rugby World Cup in Japan where they were knocked out at the quarter-final stage by England. The prospect of him turning out for Scotland at next year’s tournament in France is an intriguing one and something Townsend is sure to be considering.
The national coach has an impressive track record when it comes to persuading players to jump the fence, with Gary Graham, Cameron Redpath, Sam Skinner, Josh Bayliss, Andy Christie and Ben White all committing to Scotland after previous affiliations with England.
If Dempsey were to make the switch from Australia, a debut against the Wallabies would be an emotionally charged occasion but you get the impression he would take it in his stride.
“When they came here for the Autumn Tests last year, I went to the game and watched it live – sitting in the crowd having a few Guinnesses – and that was the first game I’d been to at Murrayfield when I wasn’t part of the squad,” he said.
“So, if I’m not playing it will be good because I can go there and have a few more beers in the stand and watch the game, and if I am playing on either team … I don’t know, it will be good either way.
“I’m not thinking about it too much. I just think it is a good thing to see those two teams play the game here.
“Is the door open? Well, it’s not closed. But if the door is closed, I’m always going to sneak through the window, I’m just one of those guys!
“I’ve got my parents coming over for the Edinburgh game in two weeks. I haven’t seen them for a while, so I’ll catch up with them, and my mum is obviously the one who’s on the Scottish side, so I’ll pick her brain about a few different things and what she’s thinking, because I know my dad doesn’t want me to bloody play for Scotland!”