30 Amazing Questions to Ask a Guy Over Text post image

30 Amazing Questions to Ask a Guy Over Text


Texting is our main mode of communication these days- it’s just the way it is, so much so that when someone actually calls you think there must be an emergency.

Asking the right questions can really open the gates for a deep, profound connection. But there is a huge difference between talking in person and chatting via text. When texting, you can’t really ask questions where answers will be long detailed stories, or where there are a lot of nuances.

Texting also isn’t the right forum to have a heavy or deep emotional conversation because a lot can get misinterpreted or lost in translation.

MORE: 225+ Amazing Questions to Ask a Guy- The Only List You Need

Texting isn’t the time to get someone’s full life story, but you can still learn a lot about another person … when you know the right questions to ask,  questions that are little more creative than:“Hey whats up?” and  “How are you today?”

And with that, here is my compilation of the absolute best questions to ask a guy (or girl) over text.

1. Have you ever accidentally sent an embarrassing text?

Being able to freely share embarrassing moments is a great way to laugh and build a connection. Although if a guy really likes you, he’ll probably hold back from telling you his seriously embarrassing moments and will give you something that doesn’t present him in too much of a negative light.

2. Which emoji best captures your essence?

Is it the winky face with the tongue sticking out? The embarrassed emoji? The screaming one? This is a silly and cute question that can also be quite telling in terms of how he sees himself!

3. What is your mantra?

We all have one, it could be a quote or saying or song lyric, something that speaks to us and motivates us and inspires us to keep going.

4. What is the greatest song of all time?

This is just a fun, lighthearted question that can also reveal a lot.

5, What is your go-to meme?

This question could take the convo to a hilarious direction, who doesn’t love talking in memes and gifs?

MORE: 20 Questions to Ask a Guy to Get Closer

6. What website do you waste the most time on?

This is a good question for follow-ups. If he says Youtube, you can ask what types of videos he gets lost in- is it cats doing funny things or greatest political debates ever? And you can ask him to send over his all-time favorite clips. Men love sharing their interests with girls they’re interested in, and love when she shows genuine interest in the things he likes!

7. What is always worth the calories?

This is a no-risk question that’s perfect when you’re just easing into things. You definitely don’t want to start with anyting too heavy, especially if you’re texting with a guy you aren’t dating yet, or don’t know super well.

8. What always makes you smile?

If you know what makes him smile, you can do more of it :)

9. What is the funniest accidental call/text you’ve ever received?

There’s a chance he doesn’t have an answer for this, but if he does you may be in for one hilarious story.

10. What is the background on your phone?

This is something he chose and looks at every day, so it’s probably significant. Finding out what it is can tell you a lot about what he values.

11. What is the cheesiest pickup line you know?

Because who doesn’t love cheesy pick-up lines?

12. How much time do you spend on social media?

This can open the gates for a bigger discussion on social media, and whether it’s enhancing or ruining our society.

13. What is your favorite date spot?

A good question to see how romantic he is … and to plant the idea in his mind of taking you to said spot if he hasn’t already.

14. Text me a picture of a place you’re dying to visit.

We all have a little wanderlust inside, so let it out by sharing places you’re dying to see!

15. What is something you can’t do that most people can?

We all have something we’re embarrassingly bad at, and maybe we don’t freely admit it to just anyone, but it can be fun to talk about with someone we’re close to.

MORE: 50 Great Questions To Ask A Guy

16. Say something sweet to me using only emojis.

OK, this is more of a command than a question, so hopefully, he’s down! It definitely invites creativity and some laughs.

17. What is the most cringe-worthy thing you’ve seen someone post on social media?

People can be a little shameless with social media, something it may seem like they forget how many people are actually going to be viewing their posts, so I’m sure he has experienced secondhand embarrassment more than a few times!

18. If you had to give up one of your five senses, which would it be?

This question is harder to answer than it seems at first and will show you what he really values. Plus, it can take the conversation to a deep and interesting direction.

19. Are you an introvert or extrovert?

An easy question to answer that can tell you a ton about the other person.

20. What would your perfect day look like?

This will show you what he values and what makes him happy, all good things to know about a person, especially if you’re dating or have an interest in dating them.

MORE: 103 Sexy Texts That Turn Him On 

21. What is your first reaction when someone calls you on the phone?

Does he assume it’s an emergency? That they are butt-dialing him? That this person is just a weirdo because who actually calls in this day and age? The answer can be telling and amusing!

22. Can you answer five questions using just pictures?

This can turn into a fun game and is a great way to learn about him. The questions can be anything, you can choose from this list or check out this mega-list of questions.

23. If you just inherited a million dollars, what’s the first thing you would buy?

Because it’s always fun to dream!

24. What do you miss most about being a kid?

This question can be a bit more telling without being too invasive, so it’s perfect to ask a guy you’re a little more comfortable with. It’s also a great question to ask in person because it can lead to an interesting conversation.

25. What is always worth the wait?

Waiting sucks, but some things are always worth it. What is always worth his wait?

MORE: 26 Goodnight Texts That Will Melt His Heart 

26. What is your kryptonite?

Even Superman has a weakness … what’s your guy’s?

27. What movie can you watch again and again?

This is an innocent question that will tell you a lot about him as a person. Is he into humor? Psychological thrillers? Action movies?

28. How many phones have you broken or lost?

It happens to the best of us … and happens to some people a lot more often than others.

29. Aside from murder, what is one thing you would never do for all the money in the world?

Men like to present a front of being all macho and tough, but everyone has their line in the sand regarding how far they’ll go!

30. Tell me the most random piece of trivia you know.

Because who doesn’t love to share their useless knowledge?

I hope this article gave you some good ideas for questions to ask a guy over text to get to know him a little better and have a little fun. Now I have a question for you. Do you know what inspires a man to commit to a woman? Do you know what makes him see you as a rare gem that he can’t let go of, a woman he wants to be with forever? If not, read this next: The #1 Things Men Desire in a Woman

And now another question. Do you feel like he might be losing interest? Does he seem to be pulling away? If so, you need to read this too: If He’s Pulling Away, Do This...

Want more questions? Be sure to read these articles as well:

300 Rejection Proof Conversation Starters

Ask A Guy You Like These 20 Cute, Amazing Questions

Flirty Questions to Ask a Guy Over Text

Sexy Questions to Ask Your Boyfriend 

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you...

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