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Originally Posted by Exulted Unicron
for example, Charles Nungesser vanished in 1922, do you reckon Indy got worried and went looking for him?
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It's doubtful that they ever saw each other again and even more doubtful that Indy went searching for him (in my opinion).
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Originally Posted by Exulted Unicron
I like to think he did keep in contact with alot of his acquaintances across the years. In the Lost Journal, there was a letter he was going to send to Ned, but what do you guys think?
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Like IndyBr said, where is the letter he meant to send?

I can't find it.
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Originally Posted by IndyBr
Maybe he even lost contact with Remy! In the Lost Journal there is that note about the Peacock's Eye, but if it's there in the Journal... then I think we can safely believe it wasn't sent.
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True, but he must have had Remy's current mailing address which indicates that they were still in touch (according to "Lost Journal").
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Originally Posted by Exulted Unicron
I mean who knows, perhaps when Indy, Shorty and Willie were leaving the villiage in Mayapor, Indy went to see his old friend Jiddu Krishnamurti.
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Probably not considering Krishnamurti was living in California at the time (He did give a lecture tour in India sometime in the '30s but I don't know what year). That said, Indy was well aware of Krishnamurti's life events that followed so either they were in touch or Indy kept up to date by reading about him.
Not a complete list here's my take on the likelihoods:
Princess Sophie: Yes, They did met again but whether it was by coincidence or planned, is unknown.
Infant Barthélemy: Yes. Somehow, Indy knew that the baby boy grew up to be Barthélemy Boganda, the 1st Prime Minister of the Central African Republic and "the father of his country".
T.E. Lawrence: Very likely
Hemingway: Very likely
Howard Carter: Very likely
Norman Rockwell: Strong possibilty
Lowell Thomas: While they weren't really friends, it's very possible they encountered one another again
Edith Wharton: Possible
Robert Goddard: Possible
Eliot Ness: Possible
Sidney Bechet: Possible
Krishnamurti: Possible
Siegfried Sassoon: Possible but doubtful
Schweitzer: Possible but doubtful
Charles Nungesser: Doubtful
Sixtus & Xavier: Doubt it
Picasso: Doubt it
John Ford: Who knows?
Edison: Who knows?
Charles de Gaulle: Who knows?
Tolstoy: No. Died 1910.
Kafka: No. Died 1924.
Frederick Selous: No. Killed a few months after "Phantom Train". (His other buddies in the Royal Fusiliers were based on real people but their real names & fates are unknown.)
Theodore Roosevelt: Probably not. He died in 1919 but there's a strong possibility for his son, Kermit!
Staying in contact with these 2 guys adds a whole new dimension to "Crystal Skull":
Paul Robeson: Likely although very, very bad for Indy during the McCarthy era!
Ho Chi Minh: Doubt it but, like Paul, very bad for Indy's government profile.
Many of his fictional friends & acquaintances died during the episodes. Of the ones who lived:
Remy: Very likely. (If "Lost Journal" is taken into account then definitely, YES!)
Vicky Prentiss: No, not until the were reunited by a chance encounter 76 years later.
Marcello, Charles & Cunningham: Possibly during WW2 (but not likely).
Chinese family: Doubt it.
Omar: Awhile back, a few of us were imaging the possibilty that he grew up to be the owner of Omar's Garage in "Raiders"!
Meto: Indy's classroom in "Crystal Skull" has a table with many artifacts. According to the book, "Ultimate Guide", one of them is Teddy Roosevelt's pair of binoculars but we know that Indy gave them to Meto. Either they met again OR Indy kept the empty, binocular case for himself.
Not a friend but he meets Al Capone again in "Genesis Deluge" (even though it doesn't correspond with the events in "Mystery of the Blues").