lmao 'sad'. Reminds me of a certain cut-throat slum lord's son.

Imagine changing your whole living situation then having that long-term living arrangement you never got a signed document for ended by someone else based on how they're feeling.

He should've gotten a subletting agreement on paper and really shouldn't be a dick to the leaseholder but all we've seen is your side of things and he might have his reasons. If you let him move in there then by law he is a tenant, legal documents or not.

MA law prevents tenants from having their lives upended without notice. You're still evicting them and they still have to go through the sucky process of moving out but you're not allowed to just call the police and throw someone and their belongings off the property you allowed them into the second you're not feeling it anymore. Big whoop. If it was happening to you, you'd call yourself a victim of a landlord, not a freeloader. Not his fault you didn't ask for rent; you let him live there rent free, that was the agreement you both abided by until you decided it was a retroactive problem.

There is a clear separation between property/habitation and relationship status in the eyes of the law so unless they are putting you in danger by living there you're just looking for a way to make their life harder than you're already about to make it.

Serve him the papers and suck it up. Spend time elsewhere if you really can't deal with them leaving you alone and staying in a separate area of the apartment. At least you're not the one moving out.