English Small Talk: Questions with When and How

Small Talk Dialogues in English Asking Questions with When and How

English Small Talk:

Common Questions with When and How

This the last post in our Small Talk Questions Series: you can find
Who & What Worksheets and Lesson Here
Where & Why Worksheets and Lesson Here

Natural English pronunciation can be quick, and we’ve recorded 30+ dialogues and 50+ common questions that you can use to improve your English listening skills. We’re pure conversation, so we don’t have any grammar lessons, and we use our natural tone, intonation and speed, so that you can mimic and feel confident in your skills when you meet other English speakers.

How can I improve my Speaking skills?

We’ve put together a Speaking Practice clip at the beginning of every audio player. We’ve taken 5 common English questions, and we’ve repeated them in American and British accents. We give you a little time after each question to repeat it, copying our quick and fluent way of speaking. Easy!

How can I improve my Listening Skills?

Listen to naturally spoken English. The more you listen, the easier it gets. We’ve put together worksheets with Fill in the Blanks activities to help you connect Writing with Listening in order to improve your Listening Skills and help you focus during the English dialogues. We also include all of the transcripts, so you can go back and read anything that you may have missed.

When vs What time

When are you getting here? – I’m pretty open about the time.
What time are you getting here? – I need to know the time specifically.
Just a little bit of a change in the meaning here between the two questions.

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Grab our Free ESL Intermediate Worksheets with Pronunciation Guides + MP3 Downloads and Full Transcripts Here:  

These worksheets take around 10 minutes in the classroom or 15-20 minutes for self-study. They’re the perfect addition to your adult English class, because they use real, naturally spoken English to give your students confidence.

So let’s get started with our Common English Questions with When and How!

When Questions with Do and Does

English Speaking Practice:

Common English Question: American accent.

Beep. Repeat it! Use the accent, tone and speed to sound like a native English speaker.

Common English Question: British accent.

Beep. Mimic! Have fun with it, record yourself, enjoy the natural flow.

When do you wanna leave?
When does s/he wants us to be there?
When does it start?
When do you normally go to work?
When does she usually workout?

Transcript Dialogue #1:

Are you going to Sam’s going away dinner tonight?

Yeah, for sure, when does the whole thing start?

He said around 5 or 6, but I’ve gotta leave early so I’ll probably be there by 5.

Transcript Dialogue #2:

Hey, boss wants us to come in early on Friday to wrap up our project.

Wow, okay, when does he expect us to be there?

Oh, just like, half an hour early, I think it’s the only time he’s free all week.

Transcript Dialogue #3:

I didn’t know you went to this gym.

Yeah, I’ve been going here the last few months, but I’m not usually here on Tuesdays.

Ah, when do you normally come up here?

After work on Mondays and Wednesdays.

When Questions with Did

Speaking Practice: Common English Questions:

When’d you leave last night?  What time did you end up leaving?

When’d they move in?

When’d he get that? When’d he buy those?

When did he say he wanted to meet us?

When’d you go there?

*Sarcastic setup: Since when do you…
Example: I made dinner!
Since when do you cook? (I’m a little skeptical/doubtful, because you don’t usually cook)
Since I started getting all the ingredients sent to my house in a nice, little package every week.

Transcript Dialogue #1:

(At work, a restaurant or bar)

We were totally slammed last night, you’re so lucky you had the evening off.

Oh, really, when’d you end up leaving?

We started closing up at midnight, but we weren’t out of here until one.

Transcript Dialogue #2:

I’m really not sure if I have time to head to the store before we meetup with Liz and them. When did they say they wanted to meet us?

John told me 6:30, so I think you should have plenty of time.

Transcript Dialogue #3:

I can’t believe he’s selling that old car, when’d he even get that? He’s had that thing forever.

Well, he was driving it when we were in high school, I actually think it was his dad’s for a while.

When Questions with Is and Are

Speaking Practice: Common English Questions:

When’s that?
When is she moving?
When’s he coming over?
When are you heading out later?
When are they getting married?

Sarcastic: Doubtful
Since when are you…
We got along really well and his dog is really cute.
Since when are you a dog person?? I thought you hated them.
Well, this one was really small and pretty cute.

Transcript Dialogue #1:

Okay, so let’s figure out this month.

Well, I’ve got a wedding on the 24th, and I think Bobbi’s planning on getting everyone together.

Oh okay, when’s that?

Not sure yet, but I’ll let you know when that comes together

Transcript Dialogue #2

I think Helen and Liz are gonna need some help moving all their furniture next week.

Yeah, we can do that, when’re they moving?

They’ve already started packing, but I think they’re trying to move the big stuff Thursday and Friday.

Transcript Dialogue #3:

Hey when’re you coming over later?

Depends, when do you want me to be there?

4, latest 5 probably.

When Questions with Was and Were

Speaking Practice: Common English Questions:

When were you planning on leaving? (less direct than When are you leaving?)
When was the last time we did that?
When were they thinking about having it? about/of
When was her birthday?
When were you supposed to be there?

Transcript Dialogue #1:

Oh crap, I think I’m really late.

When were you supposed to be there?

Well, I just re-read the email and I think I was supposed to be there 20 minutes ago.

Transcript Dialogue #2:

When was the last time we saw each other? Right before you moved, right?

Wow, yeah, I think that was, what, 2010? 2011?

Yeah! When’d you get back into town?

We moved back last month! It’s been awesome being back.

Transcript Dialogue #3:

Hey, I’m about to head over to Jerry’s to watch the game.

And, when were you planning on going to the store?

Oh, sorry, I totally forgot, I’ll go on my way home.

When Questions with Have and Has

Speaking Practice: Common English Questions:
This setup is usually used to express doubt or sarcasm.
It doesn’t usually require an answer, but simply conveys how the speaker feels about the situation.

When have I ever been interested in that?
When have you ever wanted to do something like that?
When have you ever done that?
When has she ever been into that?
When has he ever said that?

Transcript Dialogue #1:

I think I’m gonna join the softball team.

And when have you ever been into softball? Or team sports for that matter. (I really don’t think you should join the team.)

Okay, look I’m open to trying new things, it could be fun.

Transcript Dialogue #2:

Okay so I’ve got 3 or 4 people coming over later to help paint, should I invite Max?

Uhm, when has Max ever been good at painting? (In other words, I think inviting Max is a bad idea)

Oh yeah, I almost forgot. The last time I tried to get him to help was a disaster.

Transcript Dialogue #3:

Look, I’m just saying, when have you ever seen him be nice to someone, just because?

Yeah, I think you’re right, last time he was this nice to me, he only wanted me to give him a lift somewhere.

When Questions with Would

Speaking Practice: Common English Questions:

When would you like to go out?
When would you want to meet up?
When would she be available? (A little more formal, great for on the phone or at work)
When would we start?
When would they want it to be?

Transcript Dialogue #1:

Okay everyone, when would you like to meet up this week? My schedule is pretty open.

Tuesday and Thursday works for me.

Transcript Dialogue #2:

Hey is it alright if my sister comes by to pick up my stuff? I can’t make it out today.

Sure, when would she get here? I’ve just got a few errands to run.

No problem, she can probably work around your schedule.

Transcript Dialogue #3:

Hey can you come in earlier on Tuesday?

When would you need me? I finish my classes at 2.

If you could just come in at 3, that would be great.


How Questions with Do and Does

Speaking Practice: Common English Questions:

How do you say this?
How do they make it taste so good?
How do you know that?
How does he do that?
How does it work?

Transcript Dialogue #1:

Hey, can you help me for a second?

Sure, what’s up?

How do you say this word?

Oh, ‘aisle’, like in a supermarket.

Transcript Dialogue #2:

Hi there, this is my friend Vince.

Hey man, how’s it going? How do you guys know each other?

Transcript Dialogue #3:

Wow, the fish tacos here are amazing. How do they make it taste so good?

I know, right, the chef is amazing, he’s really turned the whole place around.

How Questions with Did

Speaking Practice: Common English Questions:

How did you do that?
How did you find out?
How did he hear about it?
How did they decide what to do?
How did they figure it out?

Transcript Dialogue #1:

Is it your first time at this language exchange?

Yeah it is, I can’t believe how many people are here!

Yeah it’s my first time too. How did you hear about this place?

Actually, I found it on Facebook, and I saw that the event was tonight, so I just showed up.

Transcript Dialogue #2:

Okay, so the total for the rental car comes out to $415.

What? How did they come up with that number?

Well, there’s the base price, which we saw online, but then there’s about 4 other taxes and fees we have to pay on top of that.

Transcript Dialogue #3:

Hiya, what’s in the big backpack?

Oh, I’m just coming back from my first spin class.

Oh yeah? How’d you find it?

Yeah, it was way harder than I thought it was going to be. I’m exhausted!

How Questions with Is and Are

Speaking Practice: Common English Questions:

How are you getting there?
How are you doing?
How is it going?
How is that possible?
How is that supposed to help?

Transcript Dialogue #1:

So my brother has just finished his first month at university.

Oh yeah? How’s he liking it so far?

Yeah he’s loving it! It sounds like he’s found his crowd already, he probably won’t want to come home.

Transcript Dialogue #2:

I heard about this Russian guy who is trying to travel around the world without spending a single dollar.

How is going to do that?

The article say he’s just going to work for room and board, like odd jobs and manual work in exchange for free rides to the next city. He’s made it to Spain already!

Transcript Dialogue #3:

Hey man, how’s work going? I heard you started a new job?

Yeah, I mean, I’m still trying to get settled and learn the ropes, but yeah it’s great, and so much more interesting than my last job!

How Questions with Was and Were

Speaking Practice: Common English Questions:

How was she?
How were you able to do that?
How was your trip?
How was the game?
How was hanging out with your friends?

Transcript Dialogue #1:

Hey, you’re home early, how was going out with the girls?

It was great! Everyone had something to do tomorrow, though, so we all decided to head home a little earlier.

Transcript Dialogue #2:

Hey, how was your interview, was it good?

I mean I think so, it’s always so hard to tell, you know? I think I made a good impression, and I said everything I wanted to say.

When do you think you’ll hear back?

They said they’d call me sometime this week, fingers crossed!

Transcript Dialogue #3:
Our trip was amazing, we spent 3 months in Europe and then 6 months in Asia.

Wow, that’s awesome, how were you able to afford 9 months of traveling?

We actually worked some of the time, and we saved up a lot before we left.

How Questions with Have and Has

Speaking Practice: Common English Questions:

How have you been feeling?
How has your week been going?
How have your folks been?
How has she been able to do that?
How have you been doing that?

Transcript Dialogue #1:

Hey, how’ve you been feeling? I heard you were sick earlier this week.

Yeah, not 100%, but definitely feeling better than before.

Transcript Dialogue #2:

Jenny is still traveling! She’s been flying all over the place. It’s crazy.

How has she been able to afford such an expensive trip?

I think she’s been saving up for the past 2 years for this.

Transcript Dialogue #3:
I can barely get through the day without listening to music.

Wait, how have you been listening to Spotify on your phone? I can’t even get a single bar of service in here.

Oh, I got the Wi-Fi password from the manager, I’ll give it to you.

How Questions with Would

Speaking Practice: Common English Questions:

How would you do that?
How would you fix this?
How would you feel?
How would I know?
How would you get there?

Transcript Dialogue #1:

Look, I’m just saying I could do the job better than her.

Oh yeah, how would you do that?

Well, first I’d start by hiring a few new people and organizing the entire back room, some things should have more priority.

Transcript Dialogue #2:

I don’t know why she got so upset about it.

Well, look at it this way, how would you feel if you were the one who organized this big party and everyone canceled.

Well, I dunno, I probably wouldn’t have expected everyone to just drop everything on a holiday weekend to come and party.

Transcript Dialogue #3:

Hey I really need some help with this project, what’s this whole section about?

How would I know? I don’t even work in your department.


Teachers and Intermediate Students: Grab our Free When and How Worksheet Packages 


Awesome guys! You’ve gotten through all six question words in our common English questions series: You can check out the others here:
Who & What Worksheets and Lesson Here
Where & Why Worksheets and Lesson Here

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