Regrets &What Ifs
Third conditional · should have · I wish I had…
Your level · You are here
Get Talking · Section 1
5 minStart the conversation
What's one small decision you'd change if you could go back — nothing dramatic, just a 'what if'?
Tell your partner about a mistake that turned out to be lucky. If you hadn't made it, what would have happened?
What's one thing you should have done differently five years ago?
Grammar · Section 2
8–10 minThird conditional & regrets: should have, I wish I had...
Unreal past: IF + HAD + past participle, ... WOULD HAVE + past participle. Both parts are imaginary — neither happened.
- The THIRD CONDITIONAL talks about an UNREAL PAST — a condition that did NOT happen, and its imagined result.
- Form: IF + PAST PERFECT (had + past participle), ...
- WOULD HAVE + past participle. 'If I had studied harder, I would have passed the exam' means I did NOT study harder, and I did NOT pass.
- Both halves are contrary to fact.
- SHOULD HAVE + past participle expresses REGRET or CRITICISM about a single past action, without the full if-clause: 'I should have called her' (I didn't, and I regret it). 'You shouldn't have said that' (you did, and it was wrong).
- I WISH + PAST PERFECT expresses a personal regret about the past, focused on the speaker's feelings: 'I wish I had listened to you' (I didn't, and I regret it now) — this is very close in meaning to 'I should have listened to you', but 'wish' is more personal/emotional and 'should have' can sound more like practical advice or criticism.
- Note the negative forms: 'if I hadn't been late...' / 'I wish I hadn't said that' / 'I shouldn't have eaten so much.'
- Imagining a different past result — 'If I had left earlier, I would have caught the train.'
- Criticising or regretting a specific past action — 'You should have told me.'
- Personal regret focused on your own feelings — 'I wish I had said yes.'
- Negative regret — 'I wish I hadn't...' / 'I shouldn't have...'
- Explaining how a small past event changed everything — third conditional chains.
e.g. If I had known, I would have told you.
| Form | Focus | Example |
|---|---|---|
| If + had + p.p., ... would have + p.p. | imagined alternative past result | If I'd left earlier, I would have caught it. |
| should have + p.p. | criticism/regret about one action | You should have told me sooner. |
| shouldn't have + p.p. | criticism of something that DID happen | I shouldn't have eaten so much. |
| I wish + had + p.p. | personal, emotional regret | I wish I had studied harder. |
If I had known you were coming, I would have cooked more.
If she hadn't missed the train, she wouldn't have met him.
I should have booked the tickets earlier.
You shouldn't have told him — it wasn't your secret to share.
I wish I had studied medicine instead of law.
I wish I hadn't said that to her.
Not this
If I would have known, I would have told you.
Say this
If I had known, I would have told you.
Never use 'would have' in the if-clause — only 'had + past participle'. 'Would have' belongs only in the result clause.
Memory tip
Third conditional = 'past that never was'. Two steps back from now: HAD (not was), WOULD HAVE (not will).
Natural English
In fast speech, 'would have' contracts to 'would've' (often heard as 'would of' in writing — this is a common spelling MISTAKE, never write 'would of').
Step 1 — Build the sentences yourself
Build the sentence → spot the natural chunks → say it aloud → reply like a real conversation.
1.Rebuild the sentence — then say it aloud.
2.Rebuild the sentence — then say it aloud.
3.Rebuild the sentence — then say it aloud.
4.Rebuild the sentence — then say it aloud.
Step 2 — Produce the form from memory
There isn't one "right" answer — write a natural version, then compare with the model.
Q1.Best correction: 'If I would have known...' should be: (answer in a few words)
Step 3 — Check your choices
Question 1.Which is the correct third conditional?
Question 2.Which expresses regret about a single past action, without a full if-clause?
Question 3.Which is a correctly formed negative regret with 'wish'?
Question 4.Which sentence means 'she did NOT miss the train, and did NOT meet him'?
Vocabulary · Section 3
5–7 minWords & phrases to learn
Hindsight
understanding of a situation only after it has happened
In context
"In hindsight, I should have taken the job offer."
Now try it yourself
Use 'hindsight' about a past decision of yours.
Turning point
a moment when a decisive change happened
In context
"Meeting her was the turning point in my career."
Now try it yourself
Describe a turning point in your own life.
Miss an opportunity
fail to take a good chance
In context
"I missed the opportunity to travel when I was younger."
Now try it yourself
Talk about an opportunity you feel you missed.
Look back on
think about a past event now
In context
"Looking back on it, the decision seems obvious."
Now try it yourself
Say what you 'look back on' with pride or regret.
What if
used to imagine an alternative situation
In context
"What if we'd never met that day?"
Now try it yourself
Ask your partner a 'what if' question about their past.
Second-guess (yourself)
doubt a decision after making it
In context
"I keep second-guessing whether I made the right choice."
Now try it yourself
Describe a decision you often second-guess.
Make amends
do something to correct a past wrong
In context
"He tried to make amends for missing her birthday."
Now try it yourself
Discuss a time someone tried to make amends with you.
Water under the bridge
a past problem that is no longer important
In context
"That argument is water under the bridge now."
Now try it yourself
Name something in your past that is now 'water under the bridge'.
Pick at least three words from above and use each one in a sentence about your real life. Say each one aloud before you write.
Ask your teacher (or a partner) a question that uses one of today's words. They reply using a different word.
Rank today's words from most to least useful for you this week. Defend your top choice.
Finish: "Honestly, I'd say…" using one of today's words.
Tip: aim to reuse at least two of these words later in the Speaking and Writing tasks.
Tap an item on the left, then tap its match on the right.
Pronunciation · Section 4
3–4 minContracted 'would have' ('d've) and weak 'have' in should/would have
In fast natural speech, 'would have' contracts heavily to 'would've' (/wʊdəv/), and after a pronoun it often becomes 'd've' (/dəv/): 'I'd've called you' (from 'I would have called you'). 'Should have' similarly weakens to 'should've' (/ʃʊdəv/). This weak 'have' sounds like 'of' — which is why 'would of' is such a common (incorrect) spelling. In writing, ALWAYS use 'would have' / 'should have', never 'would of' / 'should of'.
- • if I'd KNOWN, I'd've TOLD you
- • you SHOULDn't've SAID that
- • I WISH I'd STUdied HARder
- • she WOULDn't've MISSED it if she'd LEFT earLIER
Reading · Section 5
8–10 minThe email I never sent
Ten years ago, Leo was offered a job in Berlin. He turned it down because his girlfriend at the time didn't want to move, and looking back on it now, he says that decision is the one he thinks about more than any other. 'If I had taken that job, I would have learned German properly, I would have met a completely different set of people, and honestly, I probably wouldn't have ended up in the career I'm in now — for better or worse. I'll never actually know.'
He's careful to say this isn't the same as being unhappy with his life. 'I'm not saying I wish I'd taken it. I'm saying I wish I'd thought about it more carefully at the time, instead of deciding in about twenty minutes because I didn't want an argument.' That distinction, he says, is the turning point in how he thinks about regret now: it's not always about wishing for a different outcome, but about wishing you'd made the decision more honestly.
He kept a half-written email to the Berlin company for almost a year, asking whether the offer still stood. He never sent it. 'If I'd sent that email, maybe nothing would have changed anyway — companies move on. But I should have at least asked the question instead of just assuming the answer was no.'
What strikes him most, in hindsight, is how small the original decision felt at the time. 'Nobody tells you which Tuesday afternoon is going to be the turning point. You just find out fifteen years later, when you're describing it to someone, that it was.' He doesn't second-guess it constantly any more — mostly it's water under the bridge — but he says the lesson stuck: next time a big decision comes disguised as a small one, ask more questions before deciding.
Step 1 — Read for the overall picture: true or false?
Q1.The text says Leo definitely wishes he had taken the job in Berlin.
Q2.The text says Leo eventually sent the half-written email to the company.
Step 2 — Find the evidence and answer
Question 1.Why did Leo turn down the job in Berlin ten years ago?
Question 2.What does Leo say he actually regrets, according to the text?
There isn't one "right" answer — write a natural version, then compare with the model.
Q1.What can we infer from the fact that Leo kept a half-written email for almost a year but never sent it? (answer in a few words)
Q2.What is the main lesson Leo says he took from the experience? (answer in a few words)
Listening · Section 6
8–10 minTwo old friends looking back on a missed trip
Listening audio
Tap play to listen. Replay as many times as you need.
Show transcript
Ben:Do you ever think about that trip we almost took to Argentina, back in university?
Katya:All the time. If we'd actually gone, I think we would have stayed for way longer than three weeks.
Ben:Probably. I should have pushed harder to book it — I remember I was the one who got cold feet about the money.
Katya:To be fair, I wasn't exactly encouraging either. I wish I'd been braver about it at the time.
Ben:If we hadn't cancelled, do you think we'd still be friends now, or would we have driven each other mad after three weeks?
Katya:Honestly? I think we would have had one huge argument in about week two, and then it would have been fine.
Ben:That sounds about right. I still have the guidebook, you know — never even opened it properly.
Katya:Should we actually go now? Or is that a terrible idea twenty years later?
Ben:I don't think it's terrible. Though if we'd gone back then, we would have done it very differently — hostels, no plan, no money.
Katya:True. I wouldn't want to redo it exactly the same way. But I would love to finally see the place.
Ben:Let's actually do it this time. No cold feet.
Katya:Deal. And this time, if either of us hesitates, the other one should have already booked the flights before we can back out.
Step 1 — Listen and notice the language
Step 2 — Listen again and complete the notes
Question 1.Why did Ben and Katya not go to Argentina at university?
Question 2.What does Katya say she wishes about her own behaviour at the time?
There isn't one "right" answer — write a natural version, then compare with the model.
Q1.What does Katya predict would have happened if they had gone on the original trip? (answer in a few words)
Q2.What do Ben and Katya decide to do by the end of the conversation? (answer in a few words)
Question 1.Which phrase shows Ben admitting personal responsibility for the cancelled trip?
Exam tip · Section 7
5 minSpeaking — Cambridge B2 First Part 3/4 & Writing opinion essay (regret/hindsight topics)
Task
Speak for 90 seconds about a decision you or someone you know made, and how things would have been different with a different choice. Use at least 3 third conditionals, 2 'should have' sentences, and 1 'I wish' sentence.
Strategy
Regret and hindsight topics reward precise, varied hypothetical language. (1) Set up the real past fact first ('I didn't apply for the job'). (2) Use the third conditional for the imagined alternative ('If I had applied, I would have...'). (3) Add a 'should have'/'shouldn't have' for direct self-criticism. (4) Use 'I wish' for the emotional layer. (5) Avoid 'would of' in writing — always 'would have'.
Example
A few years ago I turned down a scholarship abroad because I was scared of leaving my friends. If I had gone, I would have learned the language properly and probably made a completely different set of connections. I should have talked to more people who'd done it before deciding so quickly. I wish I'd been a bit braver at the time — though I try not to dwell on it, because it's genuinely water under the bridge now. If anything, it taught me to ask more questions the next time a big decision came along disguised as a small one.
Practice · Section 8
8–10 minFill in the blank
Step 1 — Retrieve it from memory first
There isn't one "right" answer — write a natural version, then compare with the model.
Q1.Write a third conditional sentence about a past decision you didn't make.
Q2.Write a sentence with 'should have' expressing regret.
Q3.Write a sentence with 'shouldn't have' criticising a past action.
Q4.Write a sentence with 'I wish I had...' about a personal regret.
Step 2 — Now check your choices
Question 1.If I ____ known, I would have told you.
Question 2.I should ____ booked the tickets earlier.
Question 3.I wish I ____ studied harder for that exam.
Question 4.You ____ have told him — it wasn't your secret.
Question 5.If she hadn't missed the train, she ____ have met him.
Writing · Section 9
5 minPut it in writing
Your task
Write a 140–170 word reflective piece about a decision you (or a character) would make differently with hindsight. Use at least 5 third conditionals / should have / I wish structures, and 5 lesson vocabulary items.
Your answer
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Show model answer
Looking back on it, the turning point in my twenties was a job I almost took and didn't. If I had accepted it, I would have moved to another city, and I would probably have built a completely different network of friends. I should have asked more questions before turning it down — I decided in about an hour, mostly out of fear of change. I wish I hadn't been so quick to assume the safer option was automatically the right one. That said, I try not to second-guess it constantly; most of the time it feels like water under the bridge, not an open wound. What I did take from it, in hindsight, is a simple rule: if a decision feels small but makes you nervous, that's exactly the moment to slow down. I missed an opportunity to test that theory once — I won't miss the next one.
Speaking · Section 10
10–15 minMake it a real conversation
Role-play 'Looking back together' — two old friends or family members discuss a shared decision from the past (a trip not taken, a house not bought, a job not accepted) and imagine how things would have been different. Use at least 4 third conditionals and 2 'wish'/'should have' sentences.
Useful phrases
- • If we had..., we would have...
- • I should have...
- • I wish I'd...
- • Looking back on it, ...
- • In hindsight, ...
Speaking reflection & notes
Your work saves automatically0 words
- ADo you ever regret not taking that job abroad?
- B_______________
- AWhat would you have done differently, looking back?
- B_______________
- ADo you still think about it a lot?
- B_______________
Homework · Section 11
Take-homeTake it home
Write 8 third conditional sentences about a real or imagined past decision, mixing positive and negative forms.
Speak for 2 minutes about a turning point in your life, using at least 3 'should have'/'wish' structures.
Interview a family member about one regret or 'what if' moment in their life and summarise it using third conditionals.
Homework notes
Your work saves automatically0 words
Recap · Section 12
2–3 minWhat you've learned
- Third conditional: IF + had + past participle, ... WOULD HAVE + past participle — for an unreal past and its imagined result.
- Never use 'would have' in the if-clause; only 'had' + past participle.
- SHOULD HAVE / SHOULDN'T HAVE + past participle = regret or criticism about one past action.
- I WISH + had + past participle = personal, emotional regret about the past.
- 'Would of' and 'should of' are spelling mistakes — always write 'would have' / 'should have'.
Extra Practice
Need more practice?
Practise the grammar, vocabulary and speaking from this lesson.