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Characters from different "Star Trek" series who should meet

Worf and any Klingon from Discovery. With Julian and Miles there egging him on with questions.
Bashir: Now wait a minute, these are Klingons too?
Worf: We definitely don't talk about this breed. To anyone. We even try to avoid talking about them amongst ourselves.
O'Brien: Come on Worf, this definitely requires some sort of explanation.
Worf, pissed swipes everything off the table and lets out a rant in the Klingon language.
Bashir: What did he say?
Jadzia: I'm not sure he knows what he's saying, it definitely doesn't make sense.
O'Brien: You realize you just made us even more curious, right?
Jadzia: Something about Ambassador Spock's sister.
Bashir: Spock has a sister?
 
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I do not know if this has actually occurred on screen or not (or if anyone already said this), but I think it would be interesting if the Doctor/EMH met Zimmerman (his creator). Zimmerman's ego would make him think of himself as the Doctor's creator/god, and the Doctor would quickly surpass Zimmerman in competency, knowledge, and personal/social skills. I can imagine a jealous Zimmerman, refusing to think of the Doctor as a sentient being, but as his creation; and becoming increasingly annoyed that the Doctor, who is like Zimmerman (at least on the outside, and with regards to basic personality), surpassing him. In Greek mythology, for example, whenever a human being surpasses a god (or thinks that they can), they meet horrific consequences.
Honourable mentions: Gul Dukat and Kodos the Executioner, and Lore and Ruk (from TOS episode: What are little girls made of?).
Thanks for reading, and I apologize if any of my English was strange - English is not my first language.

The sixth season episode "Life Line" is all about Zimmerman meeting with the Doctor. They did not get along very well.
 
Drs. McCoy and Pulaski would have made a curmudgeonly medical team.
Hell, they could just reveal that Pulaski was McCoy after the gender reassignment surgery. ;)

I'd like to see security chiefs Chekov and Worf clash and then ultimately bond over their shared Russian upbringing.

It'd be neat to see young Tuvok and Captain Sulu together in a more interesting story than "Flashback."

McCoy and the EMH would be entertaining as hell.

They're from the same series, but I've long thought that it'd be fun to see Cyrano Jones and Harry Mudd trying to out-con each other. Heck, Mudd and Quark could be fun, too. Which one of them would be more underhanded?

I have any idea for an unexpected meeting between a TOS and a DS9 character, but as the circumstances cross over into story idea territory, I'll keep it to myself. :)
 
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Personally, I'd love to see Worf and Neelix. But I'd also like to see Kira and B'Elanna in some situation that gets them out of their comfort zones...to see how two of the toughest women of Star Trek would work together.
 
Quark and Mudd for sure but I think someone might have said that.

I’d like to see Scotty join forces with Bashir and Miles, that would be a fun.

I always thought it could have been interesting to see the doctor, Data and Odo in a room talking about how none of them understand their own existence. It’s funny that every series has at least one character facing this dilemma.
 
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I'd like to see Prime Kahn and Mirror Kira duke it out.

Garak and Sloan in a clash of wits.

I'd like to see Ro Laren and Eddington do a Maquis Bonnie & Clyde thing.

Sela arrive on DS9 during the Dominion War and unnerve Worf.
 
The Duras sisters would sneer at B'Elanna calling her a mongrel half-breed and B'Elanna would in kind "accidentally" arrange a warp core breach on their BoP.
 
Worf and any Klingon from Discovery. With Julian and Miles there egging him on with questions.
Worf removes his hairpiece.
WORF: By Kahless, it is good to be rid of that thing!
Bashir: Now wait a minute, these are Klingons too?
Worf: We definitely don't talk about this breed. To anyone. We even try to avoid talking about them amongst ourselves.
O'Brien: Come on Worf, this definitely requires some sort of explanation.
Worf, pissed swipes everything off the table and lets out a rant in the Klingon language.
Bashir: What did he say?
Jadzia: I'm not sure he knows what he's saying, it definitely doesn't make sense.
O'Brien: You realize you just made us even more curious, right?
Jadzia: Something about Ambassador Spock's sister.
Bashir: Spock has a sister?
Bashir: Wait, which one's Spock?
 
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