Italian. It's certainly got its prepositions, and which are notoriously variable: you can be in a store but you have to be at a bank and under a car repair place and who knows what. You walk at foot and ride in a bike. But can we use any of these broken-down old prepositions to indicate who gives what to whom? Oh NO, that'd be too easy. We have to 1 use inflected pronouns which 2 change their spelling when they combine and 3 are often truncated and 4 have to agree with the number and gender of the participle ending -- but only in the third person, and only with certain verbs. So to say "I gave it to her" you WOULD have to say "To her it I have given" (because they use the compound imperfect as their standard past tense, and call the regular old preterite past the "passato remoto" and don't use it -- so you can't say "I went" -- you have to say "I have gone," which means "I went") -- which would be, at any rate, "Le la ho dato," but Le becomes Gli and adds an E and combines with la (we're assuming what I gave her was feminine, like, say, a bus) AND it contracts AND the participle changes to agree with the bus, so you end up with "Gliel'ho data." Which is a lot of fucking work for a simple present indicative sentence with a couple of pronouns.
And that's just the pronouns. The verbs are all inflected, so it's madness Haven't these fucking Romans ever heard of a goddamn modal? I know, I know, all the Romance languages are like that, and that English has its share. But English's share of ending-changes is tiny. What, third person singular present indicative? I drive he drives? -- and one more change from present to past, drive-drove? Yeah, but that's it. This fucking language has to change six times per tense, times maybe another five tenses that all have their own unique sets of endings. All of which are subject, naturally, to a large set of irregularities and various spelling changes to preserve hard and soft sounds across the plethora of various endings that stems can take on.
And that's just the grammar. The lexicon is its own madness. Since this impoverished language has half as many words as English, there are about sixteen different English senses for every one Italian expression. Which is partly why the prepositions are so crazy for English speakers: they rely on different prepositions to inflect a given word in different directions.
Then there's the subjunctive, which allegedly represents a whole other category of proposition-force -- call it the that-I-walk rather than the I-walk -- that doesn't exist in English because it serves no purpose: while you can say "You walked," you have to say "I'm glad you walkebbered." Because being glad about something obviously necessitates an entirely separate dependent verb system. With 24 different endings, of course (2 number x 3 persons x 4 tenses).
And to top it all off, no one speaks Italian. Even today, regional dialects, which can differ dramatically from "standard" (originally Florentine) Italian, are widely spoken. And we're talking major syntactic variations, not just pronunciation.
So simply trying to buy bread is like living through that scene in Monty Python's "The Life of Brian" when the Centurion is correcting the grammar of Brian's graffiti. "A! No, E! No, I! Plural, genetive, third declension! RomanI ..."
On the other hand, the nice thing about Italian is that about 80% of the lexicon has an English congnate, so if you can get the hang of where to add an O and where a ZIONE you're in good shape.