It's possible, unless for some reason a newer update changed that. It's a bit difficult but it is possible. Wait for the 4th chance they give you to flip the steak and click the button for the spices properly, if I'm not mistaken
Its possible you just got to cook the steak right. I got that route, I think I will mess up the steak in my next playthrough just to see the original route. I think in the original it was impossible to win the bet. But in the new update you can win
