This question is very hard to answer broadly, but I can contribute one tessera to a hopefully larger mosaic:

I'm currently working on some Anglo-Latin poetry about the early battles of the Hundred Years War with the French at Crécy and with the Scots at Neville's Cross. The author is, just based on the complex rhyme scheme and educated allusions, probably a monastic of some kind. The poems are explicitly political, and use puns to make fun of the French and Scottish leaders. Most of the puns would be hard to translate into English, but the one that works best is probably Lord Henry Percy piercing his way through the enemy line.

This poet isn’t telling me about his thoughts looking up at the stars, though others on the sub might tell you about all kinds of cosmological considerations and discussions over the period. He’s not complaining about getting up in the morning, though others might tell you about scribbled notes in manuscript margins where scribes complain about their work (the most famous of these is in London, British Library, MS Egerton 88 f. 26 where a scribe has written in the Ogham Irish script alluding to his hangover). But I find my poet relatable because he approaches political subjects with humor, and I don’t think that’s something that only I share with him. There’s even some chronicle evidence that parts of his poems are adaptations of short verse taunts made in camp. You could characterize this as the poet making his own version of a popular text-meme like “i lik the bred” in order to make his poem funnier or more engaging.

Being able to just randomly approach a citizen and strike up a conversation would be constrained by language, but given Tardis or other fantastic translation technology, I think we could have engaging conversations with our medieval counterparts. One of the extended jokes my poet makes is telling the story of how David Bruce, the Scottish leader at the time, allegedly defiled the font during his baptism because he couldn’t control his bowels. And Chaucer’s Miller’s Tale in the Canterbury Tales is full of jokes about sex. So in terms of humor, at least, I think there would be plenty of connections to make.

NB: My poet and Chaucer are from the fourteenth century, fairly late. The hungover scribe is from the ninth century. None of them are from mainland Europe.

For the political Latin poems, A. G. Rigg, “Propaganda of the Hundred Years War: Poems on the Battles of Crecy and Durham (1346): A Critical Edition,” Traditio 54 (1999), 169–211.

For chronicle evidence of battlefield taunts, Geoffrey Baker, The Chronicle of Geoffrey Le Baker of Swinbrook, trans. David Preest (Boydell Press, 2012), 58-9.

For Chaucer’s Miller’s Tale, both editions of the original and Modern English translations are easily accessible. For an edition, I am partial to The Riverside Chaucer, ed. Larry Benson.

For hungover scribe, Damian McManus, A Guide to Ogham, Maynooth Monograph 4 (Maynooth: An Sagart, 1991), 133.