Could a modern english speak with a person from the medieval in england?

Middle English was spoken in England from ~1150-1500, what one might call the "high middle ages" and the late medieval period. This question and associated questions has been asked relatively frequently on this subreddit:

"How different was spoken Middle English from the spoken English of today?" answered by /u/itsallfolklore
"If I was to travel back to 12th century England, would we be able to easily understand each other's use of the English Language?" answered by /u/liontamarin
"I am a native English speaker with a hypothetical time machine. How far back in time in England can I go and still communicate intelligibly with the locals?" answered by /u/Kjell_Aronsen
"How did the transition from Old English to Middle English and then on to Modern English happen?" answered by /u/supalor
"Would Middle English be considered another language? Also, if it isn't another language, why has English evolved past this 'proper' way of speaking?" answered by /u/Mictlantecuhtli
"When did England transition from Middle English to Modern English?" answered by /u/texpeare
"Could a Middle English speaker and a Modern English speaker have been able to verbally communicate? answered by /u/HallenbeckJoe and /u/pensivegargoyle

Almost all of the above threads have links to other threads where similar questions are asked -- that's how common this question is on AskHistorians.

The "differentness" of Middle English roughly corresponds to how far back you go -- so a modern English-speaker would have great difficulty speaking to an English-speaker from 1100, and considerable difficulty speaking to an English-speaker from 1300 or 1450. There's different vocabulary, differences in pronunciation, and different idioms. This difficulty in intelligibility would go both ways; to a 14th century Londoner, my 21st century Midwestern American English would sound incoherently accented, and my vocabulary and the interjections I use would be baffling. But I'm familiar with Middle English, I read works in Middle English and Early Modern English (the development of the English language that followed Middle English -- think original-pronunciation Shakespeare) all the time. So could I make it work? Maybe, especially if I had time to prepare in advance -- it would just be really challenging. In that respect, it would be more like speaking another language than like speaking "my own" familiar variety of English, even though it's the same language at its core. For me as a modern person I have the benefit of centuries of scholarship on what Middle English sounded like, so I'd probably be meeting my hypothetical medieval conversation partner more than halfway.

For a comparison of Middle English, Early Modern English, and modern English, you can take the 23rd Psalm as an example:

John Wycliffe's translation of the 1380s is Middle English:

The Lord gouerneth me, and no thing schal faile to me;

in the place of pasture there he hath set me. He nurschide me on the watir of refreischyng;

he conuertide my soule. He ledde me forth on the pathis of riytfulnesse; for his name.

For whi thouy Y schal go in the myddis of schadewe of deeth; Y schal not drede yuels, for thou art with me. Thi yerde and thi staf; tho han coumfortid me.

Thou hast maad redi a boord in my siyt; ayens hem that troblen me. Thou hast maad fat myn heed with oyle; and my cuppe, `fillinge greetli, is ful cleer.

And thi merci schal sue me; in alle the daies of my lijf. And that Y dwelle in the hows of the Lord; in to the lengthe of daies.

And a 1611 translation in Early Modern English:

The LORD is my shepherd, I shall not want.

He maketh me to lie downe in greene pastures: he leadeth mee beside the still waters.

He restoreth my soule: he leadeth me in the pathes of righteousness, for his names sake.

Yea though I walke through the valley of the shadow of death, I will feare no euill: for thou art with me, thy rod and thy staffe, they comfort me.

Thou preparest a table for me in the presence of mine enemies: thou anointeth my head with oyle, my cuppe runneth ouer.

Surely goodnes and mercie shall followe me all the daies of my life: and I will dwell in the house of the LORD foreuer

(Though note that oth of the above are written, not spoken -- some things that strike the modern English-reading eye as odd, like the use of "u" where we'd expect a "v", would not be an issue, and other

Now, the contemporary 2001 English Standard Version, a revision of a 1971 translation.

The Lord is my shepherd; I shall not want.

He makes me lie down in green pastures.

He leads me beside still waters.

He restores my soul.

He leads me in paths of righteousness for his name's sake.

Even though I walk through the valley of the shadow of death,

I will fear no evil, for you are with me;

your rod and your staff, they comfort me.

You prepare a table before me in the presence of my enemies;

you anoint my head with oil; my cup overflows.

Surely goodness and mercy shall follow me all the days of my life,

and I shall dwell in the house of the Lord forever.

This is hardly informal modern English -- this isn't something you'd bust out with in spontaneous casual conversation -- but it's intelligible, the punctuation and vocabulary are all familiar, and a reader is likely to know how to pronounce these words without stumbling. I read from the Early Modern Wycliffe Bible this weekend and while a lot of it became easier to understand or to pronounce more or less without stumbling (lots of the past-tense verbs ending with "-en", lots of "-is" to pluralize where modern English just uses "-s" to puralize) I still wasn't using a full-on Middle English pronunciation or the vowel pronunciations that would have made that same text coherent to a Middle English person.