How to Ask a Guy About His Day (8 Easy Examples)

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The goal of asking a guy about his day is to actually find out, so you want to ask questions that will get you there. You can ask him directly how was his day, or you can select questions that will be situation-specific.

Ask him about his drive, his lunch, his co-workers, his roommates, his landlords, his family, his projects, his life, and you find out about his day. You also tell him that you care about these things in his life, and you may get more information from him than a “fine” or “don’t want to talk about it.”

To ask a guy about his day and get a good conversation rolling, use these 8 examples and start to understand him a little better.

How to Ask a Guy About His Day

couple having a conversation

When you want to ask a guy how his day went, it’s to start a conversation. Asking directly isn’t always the best way to do that. Ask him specific things about his day to get the chat going.

How was the commute? Was lunch okay? How was your boss today? Show that you care with these situation-specific questions.

Did Anything Good Happen on the Commute?

The commute to work is always an opportunity for an interesting event in anybody’s day, even if there is just traffic or human congestion to talk about. Finding out how a guy’s day started and ended can give you some insight into how his day went. It will also give you some insight into him.

A bad commute can make for a bad day. You aren’t looking for the best day ever kind of answer here. You want to show him that you care about how his day started, and ended, so that you can care about how he feels about that.

Did You Have a Good Lunch?

Lunch hour is for many the best part of the day. Finding out how this went for him shows you want to focus on something that isn’t serious. Talking about something light may be just what he needs, especially if the day was a little rough around the edges.



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Lunchtime is also a good time of the day for interesting things to happen, at work or at home. This could open up more avenues in the conversation. This could tell you everything you need to know about his day.

Was Your Boss Okay Today?

office lunch

If he goes to work or has a job, asking him about his boss is a good way to find out how his day went. If you have a specific situation to ask him as far as his boss or employer is concerned, then ask him. Finding out if he is okay at work with his employer, or experiencing a challenge, is an excellent way to learn more about his day.

Is Today’s News Going to Impact You at All?

Things happen in the world during the day every day. It impacts our days immediately, or it impacts our days in the long term. News of the world is a good conversation starter when you are trying to find out how someone’s day went.

If there is something big to discuss, ask him how this news made his day or didn’t.

How Do You Ask a Guy How His Day Is Going

We’ve all been there, where we are having a boring moment in our day, or want to escape our own bad day, and we want to text him to see how he’s doing. When you are already partially through the day, there are things to do and say to find out how his day is going.

Try these text or phone call starters at the mid-point of the day. Maybe just hearing from you will turn the day around for him.

How is the Cranky Secretary Today?

guy texting

If you know he’s got a cranky situation at work today, lighten this feeling up for him by asking him how this situation is going. He might just be happy that there is someone out there that commiserates with him on the bad work situations. Let him know that you are thinking of him and hope that this situation passes.

He may not say much, but he may be happy to know that you are thinking of him.

Are You Having a Good Work Day?

We can’t say that the direct approach never fails, but you can at least try this one. Just ask him how his day went. If you are getting monosyllabic answers, try to open up the conversation a little more with specifics.

At the same time, if it feels like he doesn’t really want to say anything at all, follow that lead. Give him some space before you ask more direct questions about how his day went.

Boring is Good, is Your Day Boring Today?

For many people, a boring day is a good day. That means no problems. Ask him if he is having a boring day in the hopes that he is. If he isn’t, offer suggestions on how boring you will make the night for him if he just needs a breather from the chaos of his day.

Have You Heard From Your Friend/Sister/Mom Yet?

guy smiling

This is just an example that you can tweak to fit a specific situation in his life. If he has started the day with a problem or situation where he is hoping to hear from someone or is worried about someone, ask him about something like this. Has he heard from them yet? It’s a way of showing that you are paying attention and want him to know you hope he is feeling good about the things that he is worried about.

Wrap Up – Just Ask

When you want to know how a guy’s day went or is going, be specific. Ask about the work colleague he is always complaining about, ask about his lunch his boss, or the family situation that may be bothering him. Starting the conversation with good news or a positive question is a great way to unload a bad day also.

If you are stuck, just ask him how his day went.