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Gerunds & Infinitives Advanced: Meaning Changes
B2Grammar
1. Simple explanation
A gerund is a verb ending in -ing that works like a noun ('Swimming is fun'). An infinitive is to + the base verb ('I want to leave'). In the basics lesson you learned which verbs take each form. This lesson is about harder verbs that can take BOTH forms — but the meaning changes: 'I stopped smoking' means I quit; 'I stopped to smoke' means I paused in order to smoke. You will also learn verb + person + to ('I asked him to help'), to after adjectives ('happy to see you'), and -ing after prepositions — including the trap in 'look forward to seeing you,' where to is a preposition (a small connecting word like for or without), so the -ing form follows it.
2. Detailed explanation
First, the two forms. A gerund is verb + -ing used as a thing: in 'I enjoy reading,' the word 'reading' names an activity. An infinitive is to + the simple verb: 'I hope to read it.' Many verbs allow only one form, but a special group allows both — and then the two forms point in opposite time directions. The key is time direction: the -ing form usually looks BACK at an action that is real or finished, while to looks FORWARD to an action that is a duty, a purpose, or something not yet done.
This explains remember and forget. 'I remember locking the door' — the locking really happened; now I have the memory. 'Remember to lock the door' — the locking is still in the future, a duty. Stop works by the same logic: 'He stopped smoking' — the smoking was real and happening, and he ended it. 'He stopped to smoke' — he paused his walk with a purpose: the smoking comes after the pause. Try is similar: 'Try restarting the computer' means use restarting as an experiment; 'I tried to call you' means I made an attempt, and the attempt may have failed.
Now, three pairs, word by word. 'She remembered sending the email': remembered (past feeling) + sending (the email really went — action finished before the memory). 'She remembered to send the email': remembered (she did not forget) + to send (the duty was ahead of her; then she did it). 'We stopped to buy milk': stopped (we paused our journey) + to buy (purpose — the reason for pausing). Compare 'We stopped buying milk there': stopped (ended) + buying (the repeated action that finished).
Three more patterns matter. First, verb + person + to: 'The manager asked us to stay' — ask, tell, want, expect and persuade need the person before to; English never says 'I want that you stay.' Second, adjectives + to: feelings and difficulty take to — 'I'm glad to meet you,' 'This text is hard to follow.' In 'English is easy to learn,' English is the thing being learned — the full meaning is 'It is easy to learn English.' Third, after a preposition (by, without, for, after, instead of) only -ing is possible: 'He left without saying goodbye.' The famous 'look forward to' belongs here: its 'to' is a preposition, not part of an infinitive. Finally, the perfect gerund 'having done' shows an earlier, finished action: 'He denied having taken the money.'
Remember this first: when one verb offers you both forms, ask one question — did it already happen, or is it a duty or purpose ahead? Already happened or real → -ing (remember meeting, stopped smoking). Duty, purpose, or attempt ahead → to (remember to meet, stopped to buy, tried to call). And keep three safe rules: person + to after ask/tell/want; to after adjectives like happy and easy; and always -ing after prepositions — even the 'to' in 'look forward to.'
remember / forget + verb-ing → I'll never forget meeting her. / I remember posting the letter yesterday.
remember / forget + to (duty — action not yet done):
remember / forget + to + verb → Remember to post the letter today. / Don't forget to call me tonight.
stop + -ing / stop + to:
stop + verb-ing = quit an activity → He stopped smoking. | stop + to + verb = pause in order to do it → He stopped to rest.
try + -ing / try + to:
try + verb-ing = experiment with a method → Try adding salt. | try + to + verb = attempt something hard → I tried to reach him all day.
verb + person + to:
ask / tell / want / expect / persuade + person + to + verb → She asked me to wait. / I want you to listen.
adjective + to:
happy / glad / ready / easy / difficult / hard + to + verb → I'm happy to help. / This book is easy to read.
preposition + -ing (incl. look forward to):
by / without / for / after / instead of / look forward to + verb-ing → He left without paying. / I'm looking forward to seeing you.
Step by step — how to build a sentence:
1) Choose the main verb (remember). 2) Ask: is the second action a memory of something finished, or a future duty? Finished memory → verb-ing: 'I remember sending it.' Future duty → to + verb: 'Remember to send it.' 3) If a person receives the request, place them before 'to': 'She told + me + to wait.' 4) If the first word is a preposition (without, by, look forward to), always choose verb-ing.
4. When to use it
Talking about memories of finished events: remember / forget + -ing ('I remember meeting him in 2019.')
Reminders and duties that are still ahead: remember / forget + to ('Remember to sign the form.')
Quitting a habit or activity (stop + -ing) versus pausing for a purpose (stop + to).
Experiments and methods (try + -ing) versus difficult attempts (try + to).
Requests and instructions aimed at a person: ask / tell / want + person + to.
Feelings and difficulty: glad to, ready to, easy to, hard to.
After every preposition — by, without, after, instead of, for — and in 'look forward to.'
5. When NOT to use it
Don't use to + verb after a preposition: ✗ 'without to say' → ✓ 'without saying.' The 'to' in 'look forward to' is a preposition too, so use -ing.
Don't say 'I want that you…': ✗ 'I want that you come' → ✓ 'I want you to come.'
Don't use stop + to for quitting a habit: ✗ 'He stopped to smoke last year' (this means he paused in order to smoke) → ✓ 'He stopped smoking.'
Don't use regret + to for sadness about the past: regret + to appears in formal announcements ('We regret to inform you…'); for past actions use regret + -ing ('I regret selling it.')
6. Positive examples
I remember visiting this town as a child.
Remember to water the plants while I'm away.
He stopped biting his nails last year.
We stopped to ask a local man for directions.
Try adding a little lemon — it makes the soup taste better.
She tried to call you three times yesterday.
The teacher told us to open our books to page forty.
Finding a taxi at midnight was almost impossible, but this map is easy to read.
I'm looking forward to starting my new job in June.
He apologized for having arrived so late to the ceremony.
After winning the semifinal, they went on to win the championship.
She persuaded her brother to lend her his car.
7. Negative examples
Don't forget to lock the door tonight.
She didn't stop talking during the whole movie.
He never tried to apologize for the mistake.
I'm not looking forward to the long flight home.
The manager didn't ask me to stay late yesterday.
We won't regret selling the house — it was the right decision.
8. Questions
Do you remember meeting me at the conference?
Did you remember to buy the tickets?
Why did he stop coming to the evening class?
Have you tried restarting the router?
What exactly did she ask you to bring?
Are you looking forward to the holidays this year?
9. Short answers
Yes — I remember locking it.
No, I completely forgot to set it.
Yes, he stopped to help us.
No, she just went on working.
Yes, I'm really looking forward to it.
10. Common mistakes
✗ I'm looking forward to see you✓ I'm looking forward to seeing you.Why: in this phrase 'to' is a preposition, and after a preposition English uses verb + -ing.
✗ I want that you help me✓ I want you to help me.Why: 'want' is followed by a person + to + verb; English does not build this meaning with 'want that…'
✗ He stopped to smoke two years ago and never started again✓ He stopped smoking two years ago.Why: stop + to means 'paused in order to'; quitting a habit is stop + -ing.
✗ She remembered to meet him at the station yesterday✓ She remembered meeting him at the station yesterday.Why: a memory of a finished event takes -ing; 'remember to' is only for duties that are not done yet.
✗ The teacher said me to sit down✓ The teacher told me to sit down.Why: 'say' cannot take a person + to; instructions use 'tell + person + to.'
✗ He left the room without to say goodbye✓ He left the room without saying goodbye.Why: 'without' is a preposition, and prepositions are followed by verb + -ing, never by 'to.'
✗ This exercise is easy to doing✓ This exercise is easy to do.Why: after adjectives like easy and difficult, English uses to + the base verb, not the -ing form.
11. American English notes
🇺🇸 American English
In American business emails, 'I look forward to hearing from you' is the standard polite closing — always with -ing, because the 'to' here is a preposition. In relaxed American speech you will also hear 'try and' instead of 'try to': 'Try and get some rest' means 'try to get some rest' (informal, spoken only — write 'try to'). Americans also often drop the 'to' after 'help': 'Help me carry this' is as normal as 'Help me to carry this,' and the short version is more common in speech.
12. Similar grammar — comparison
Compare
Compare remember with remind — learners mix them up. 'Remember to call her' means YOU keep it in your own mind and YOU call. 'Remind me to call her' means ask another person to help your memory: remind takes a person + to ('She reminded him to bring the contract'). Also compare this lesson with the basics lesson: there, each verb had one fixed partner (enjoy + -ing; want + to). Here the same verb has two partners, and YOU choose the meaning by choosing the form — the grammar itself carries the message.
13. Natural spoken English
'I'll never forget meeting you at that little café.'
'Oops — I totally forgot to tell him about the change!'
'Hang on, let me stop to tie my shoe.'
'Try turning it off and on again — that usually works.'
'Looking forward to it! See you Friday.'
'He asked me to give him a ride to the airport.'
14. Real-life examples
Email closing at work: 'I look forward to hearing from you.'
In the office: 'My boss asked me to finish the slides by Friday.'
At the phone repair shop: 'Try charging it with a different cable first.'
On a café door: 'Thank you for not smoking inside.'
Health news: 'He stopped drinking coffee completely after the diagnosis.'
Travel reminder from an airline app: 'Don't forget to check in online.'
15. Mini dialogue
ADid you send the contract to the client?
BYes — I remember sending it on Friday afternoon.
AGood. And did you remember to invite the designer to Thursday's meeting?
BOh no, I forgot to email her! I'll do it right now.
APlease ask her to bring the new designs, too.
BOf course. I'm looking forward to seeing what she made.
ASo am I. Try calling her first — she answers the phone faster than email.
BGood idea. I'll try to reach her before lunch.
16. Summary
When a verb takes both forms, -ing looks back at a real or finished action (remember meeting, stop smoking) and to looks forward to a duty, purpose or attempt (remember to meet, stop to buy, try to call). Requests use verb + person + to, feelings and difficulty use adjective + to, and after any preposition — including look forward to — only -ing is possible.
17. Practice exercises
Warm up with the first questions, then take the full quiz — every answer has a detailed explanation (parts 19–20 of this lesson: answer key + explanations live inside the quiz feedback).
18. The full quiz
50 questions, mixed formats, in difficulty order: easy → medium → intermediate → challenging → advanced.