Absolutely. Every scene with him is spectacular. He was born for that role. They really had some amazing casting in the show. It wasn't always perfect, but when they nailed it they really nailed it.
You stopped at dinner so I'm choosing to go the more wholesome route lol. I'd go Dean and Charlie because a bar and a burger with those 2 in particular would be a night out to remember, unfortunately none of us probably would "remember" it lol
Rufus and Bobby... I need to know what happened in Omaha. And why Rufus is still friends with Bobby despite the that he said "I will never forgive you for what happened". Also would ask Bobby if he felt any regret for what transpired and how he values Rufus as a friend.
To name a few, in no particular order. Rufus and 'old man' Dean for the crotchety banter. Balthazar and Garth for the amusing awkwardness. Donna and Ash for the good eats and untold stories.
Sam and dean, specifically season 3 Sam and dean. Just before they drifted apart a little from Sam’s demon blood and around the time dean sold his soul to save dean but their problems were a minimum
John and Cas, the main course is broken glass and the dessert is Cas breaking a chair over John’s face…
Real serious answer: Rowena and Sam. They’re two of my absolute favs and the theoretical magic knowledge I’d gain from sitting next to them while they talked would be invaluable.
Anyone Rowena goes to a fancy restaurant with does not usually come out alive- that being said I couldn't resist, I'd invite Cas to up my chances of surviving and because I love their bickering.
tough question, but i think ill go with Death and Gabriel because that dinner would be quite interesting (and also theyre both my favourite charactersss)
Can't decide between Dean and Sam or Jodi and Donna.
if it where Dean and Sam, Castiel would drop by and would be awkward , but some sort of evil creature, angry angel or other supernatural being would probably ruin the evening, and put me into mortal danger.
Jodi and Donna would be fun, proper meal, and will tell stories of beheading supernatural creatures, while dealing with teen drama and Jodi's place.
I would like to have dinner with Rowena and Sam and discuss magic and spells and the stupidity of witches who think they can steal their stuff. Rowena and Sam's relationship at the end was so wholesome, they really were mentor mentee.
I would love to hangout with the obvious Sam and Dean but I’d be too nervous I think lol so I would pick Bobby and Crowley. They are awesome and I wouldn’t be intimidated by them! 🤣
Dean and Future Dean.
But really Dean and Sam. I’d like to just hang out and have a beer with them.