Basics. Advanced Relative Pronouns: Whose, Whom, Where, When, and Why

Medium B1 | Intermediate Adverb Apostrophe Clause Complex sentence Object Possessive Preposition Pronoun Relative clause

Advanced Relative Pronouns: Whose, Whom, Where, When, and Why

Do you know the difference between "the man who called" and "the man to whom I spoke"? While basic relative pronouns are straightforward, advanced sentences require precise usage, especially in formal contexts. For instance, you must use whose to show possession ("the house whose roof leaks") and whom as the object of a verb or preposition ("the professor to whom I wrote"). Additionally, relative adverbs like where, when, and why are essential for connecting clauses about places, times, and reasons.

In this challenge, you will step into various fun scenarios to test these rules. You'll help a detective complete official crime reports using whom and whose, assist a time-traveler leaving reviews about where and when they landed, and polish a stressed college student's formal emails. You will also evaluate quirky real estate listings to ensure possession is correctly expressed.

You'll work through 11 questions presented in a mix of single-choice, multi-choice, drop-down, and drag-and-drop formats.

Try the quiz to check your knowledge!

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Adverb

✅ She sings beautifully — ❌ She sings beautiful
✅ He drives carefully — ❌ He drives careful
✅ They arrived late — ✅ a late train (same form, both roles)
✅ She works hard — ❌ She works hardly (different meaning!)

The -ly words are adverbs — they modify verbs, adjectives, or other adverbs, telling you how, when, where, or to what degree.

Pattern: most adjectives become adverbs by adding -ly, but watch the exceptions — fast, hard, late, well — that keep the same shape or change meaning entirely.

Apostrophe

✅ the dog's bone (possession) — ❌ the dog's are barking (wrong — plural, no apostrophe)
✅ it's raining (= it is) — ❌ the cat licked it's paw (wrong — possessive its has no apostrophe)
✅ don't, they're, we'll (contractions) — ❌ apple's for sale (wrong — plain plural)
✅ James's book or James' book — both accepted for names ending in s

The apostrophe ( ' ) marks either possession (the eagle's feathers) or missing letters in contractions (do not → don't). It never makes a plural.

Rule: if you mean "belongs to," add 's. If you're shortening two words into one, apostrophe replaces the missing letters. Otherwise — no apostrophe.

Clause

I missed the bus. — ✅ independent clause (stands alone)
Because I overslept. — ❌ fragment (dependent clause, can't stand alone)
Because I overslept, I missed the bus. — ✅ dependent + independent = complete sentence
I missed the bus, and I was late. — ✅ two independent clauses joined by and

A clause is a unit built around a verb with a subject. Independent = can stand alone. Dependent = needs an independent clause to complete it.

Test: does the group of words have a subject + verb AND can it be a sentence on its own? Yes → independent clause. Has a subject + verb but feels incomplete → dependent clause.

Complex sentence

✅ Because I overslept, I missed the bus. — dependent clause (reason) + independent
✅ The man who called is my uncle. — relative clause inside the sentence
✅ If it rains, we'll stay inside. — conditional dependent + independent
❌ Because I overslept. — fragment (dependent clause alone)

A complex sentence pairs an independent clause with one or more dependent clauses linked by subordinating conjunctions (because, although, if, when) or relative pronouns (who, which, that).

Pattern: independent clause = the main point. Dependent clause = the background, reason, or condition. Move the dependent clause around for emphasis.

Object

Sam fed the dogs. — direct object (what was fed)
She sent him a present. — indirect object (who received it)
She waited for Lucy. — prepositional object (after preposition)
I gave her a book. — indirect + direct object together

An object is what a verb acts on or directs its action toward. Direct = the thing affected. Indirect = the recipient. Prepositional = after a preposition.

Test: Verb + what/whom? = direct object. Verb + to/for whom? = indirect object. After a preposition? = prepositional object.

Possessive

✅ its tail — ❌ it's tail (it's = it is, not possessive)
✅ the students' essays — plural possessive (apostrophe after the s)
✅ Sarah's book — singular possessive ('s)
✅ a friend of mine — possessive pronoun (not my)

Possessives show ownership: nouns use 's (singular) or s' (plural ending in s). Pronouns have special forms: my/mine, your/yours, his, her/hers, its, our/ours, their/theirs.

Trap: its (possessive) vs it's (= it is). Possessive pronouns NEVER use apostrophes — that's the opposite of nouns.

Preposition

✅ interested in — ❌ interested on
✅ good at football — ❌ good in football
✅ depend on — ❌ depend of
✅ arrive at the station — ❌ arrive to the station

Prepositions link nouns to the rest of the sentence: time (at 5pm), place (in London), manner (with care), abstract (afraid of). Most are idiomatic — the "correct" preposition must be memorised with each verb/adjective combination.

Rule: there is no universal rule. English prepositions are learned by combination: interested IN, good AT, depend ON, afraid OF. Your native language's equivalent will often mislead.

Pronoun

✅ between you and me — ❌ between you and I (objective case after preposition)
✅ its colour — ❌ it's colour (it's = it is)
✅ She did it herself. — reflexive pronoun
✅ The person who called… — relative pronoun

Pronouns replace nouns: personal (I/me/my), demonstrative (this/that), relative (who/which/that), interrogative (who?/what?), reflexive (myself), indefinite (everyone/nobody). They carry case that nouns have lost.

Trap: pronouns are where English case still matters: I vs me, who vs whom, its vs it's. Get these wrong and it's instantly noticeable.

Relative clause

✅ The man who called is my uncle. — restrictive (essential: which man?)
✅ My uncle, who lives in Paris, called. — non-restrictive (extra info, commas)
❌ My uncle that lives in Paris — wrong (that can't introduce non-restrictive)
✅ The book that I read = The book I read — restrictive (pronoun optional)

Relative clauses modify nouns using who/whom/whose/which/that or where/when/why. Restrictive = essential, no commas, that OK. Non-restrictive = extra, needs commas, uses which/who (never that).

Rule: if you can remove the clause and still know which noun is meant → non-restrictive (commas). If removing it makes the noun ambiguous → restrictive (no commas).

B1 | Intermediate

✅ If I had more time, I would travel more. — second conditional
✅ The bridge was built in 1920. — passive voice
✅ She said she was tired. — reported speech with backshift
✅ Although it rained, we enjoyed the trip. — complex sentence with concession

These are B1 patterns — the CEFR intermediate level. At B1 you link ideas, use passive voice, handle reported speech, and manage second conditional — enough for travel, work basics, and everyday independence.

Marker: if you can explain why something happened and follow a news story, you're B1.

Medium

If I were you, I would apologise. — one rule (second conditional), but distractors like was tempt you
Answers require active thought, not instant pattern recognition
Vocabulary and context are realistic, not artificially simplified
Usually tests one rule, but the wrong answers are plausible

Medium marks middle-difficulty challenges: A2–B1, one rule tested, but with realistic distractors that require genuine understanding.

Use "Medium" when Easy feels too obvious but Hard feels overwhelming. This is where most productive learning happens — the sweet spot of difficulty.