What would be an example of the length of entry needed for 50 bits of data to give a time and location for meet-ups?
If you want grammatically correct text like that generator, then each word you choose is limited to an adjective, noun, verb, article, etc depending on the position in the sentence. Since the first word might be an article, that will only be 1 binary bit at best ("the" or "a"). Sometimes the article is constrained. The next word might be an adjective, if there are 5,000 adjectives that is 12 bits. Then another adjective or maybe a noun with 10,000 choices for the noun (13 bits).
You can see that grammatically correct or plausible phrases are more and more limiting so you need to send more words. Another factor to consider is that the adversary may figure out the encoding, so it is probably not good to have a fixed dictionary between the sender and receiver. That means the sender will need to send even more words to tell the receiver how to set up the dictionary.
The bottom line is that the generator I linked above is probably well over 50 bits, and would work.