Questions to Ask to Keep a Conversation Going Over Text

If you are reading this, we assume it is because you’ve found a potentially special guy. The most important thing in this situation is to stay true to yourself. However, there is no harm in having a little help to keep the conversation going. One day soon, you will feel comfortable enough to let the conversation flow freely. Texting someone really allows you to get to know them without having to put too much effort in. If you are a bit of an anxious person, it adds the buffer you might need to let your guard down enough to show him your best self. Be funny; intelligent, sexy, creative, or even weird. Whatever you are, work it!

But what happens when you struggle for something to say?

Luckily for you, we have come up with a plethora of suggested subjects to ask a boy about via text. These will give you some sort of understanding about your compatibility. Differences are great. But the aim is to find out if there is a feasible future between you both whilst keeping him interested. Stick with these questions to kick your relationship into overdrive and have fun!

Start small. You don’t want your future boyfriend to think you are digging too deep into his mind's eye. You want him to offer information because he feels comfortable to do so. Begin with conversations about his interests. Give him the time it takes to open up. You may have prepared a thousand questions to text a guy in these early stages of your relationship, but you don’t want to get too intense straight off the bat. This is not job interview so make sure you send a few texts between questions. Texting should be enjoyable and breezy, which is why we recommend starting with some harmless topics first.

• Where is your favorite place to eat?

  Like the previous suggestion, this is not only about compatibility but about opening up more conversations. Does he have any funny stories about his favorite restaurant? Do you? Maybe you can get a meal delivered to him as a romantic gesture. Believe me; men love a romantic gesture as much as we do. Ask about the food and compare favorite meals. Get flirty with your text and suggest he take you there for a date.

• Who are your favorite bands or artists?

  If you’re the kind of person who listens to music non-stop, you really don’t want someone around sighing and wishing you’d stop listening to your playlist. People with a similar taste in music usually get on very well. Ideally, you want to be rocking, twerking, or clubbing together. You can share trivia about each other's favorite artists and songs. Every song has a story. Share that story! If your taste differs, you may be able to introduce each other to some great artists. Also, enjoy some healthy debates. Test the waters. Do you want someone who just agrees with you about everything? Plus, you get to gush over your favorite songs as well!

• Do you enjoy reading?

  Reading for pleasure is a good signal of intelligence and a creative mind. This may not be an important factor to some people. But if you are a bookworm and enjoy a good read, you may want to consider this when texting questions to a crush. If they have no interest in literature, you may find it difficult to exist on the same wavelength. This is why asking the right things over text is so important. You don’t want to turn up to the first date and realize you have nothing in common. If he gives you recommendations, give them a try and make sure you have some to give too.

• What are your most cringe-inducing pick-up lines?

  Have a few of your own prepared as well. Any question you ask will be fired right back at you. This is a great way to see his kind of humor and turn those texts into flagrant flirtation. This lets him know you are interested. Men are attracted to women who find them funny, just as women are attracted to men who make them laugh. Give him the perfect opportunity to do so.

Here’s a personal favorite: “Are we a cat in a litter box? Because I’m diggin’ you.” Don’t worry; you can use that one for free!

You know this man well enough to be in a relationship, but that doesn’t mean you know everything about him. In fact, it is impossible to know everything about someone other than yourself. You can always dig a little deeper. But these questions aren’t only about mining for information. They are more importantly about spending time with someone who can’t be there in person and making sure they know you are listening. If you can also make them laugh and flirt along the way, you are sure to have a long and beautiful relationship. Opening up to someone can be scary, but when it is received with love and understanding, he will be so happy that he did. Couples naturally become closer the more they text, so be prepared to open up too. These questions are sure to get you sharing your philosophical viewpoints, beliefs, and genuine wishes.

• Do you believe in the afterlife?

  This is a topic of conversation that will open up endless avenues of understanding and debate. Is there a god? Has your boyfriend ever seen a ghost? What does he think about reincarnation? The list is endless. You can really see how a person works using the answers given here. He might have a spiritual side he has never shown or be passionately atheist and be passionate about science and logic. There is no wrong answer, only learning more about each other and your experiences.

• What are you grateful for, and what would you change about your life?

  Sometimes we need to take account of the things we are grateful for. It may be smart to ask your boyfriend to think about these things. Together you can come up with a plan to implement changes if necessary. Be careful with the responses to this conversation. Don’t take any chances he would make as an affront. After all, you asked the question. If this is a compatible relationship that is going somewhere, the changes you both want to make to your lives should complement each other.

• If you had to describe yourself, how would you do it?

  This question offers the perfect opportunity to give your boyfriend a lovely pick me up and let him know how much you love him. We don’t always see ourselves the way others see us. If you know how he sees himself, you will better understand his thinking behind his actions. If he expresses low self-esteem, you can help him feel more confident. He may even return the favor.

• Do you want to go on an adventure with me?

  You don’t need money to go on an adventure. You can take a picnic and go for a hike. You can visit free galleries and give him the guided tour, even if the pair of you know nothing about art. This is an open question with endless possibilities. Encourage his input and see where it takes you.

These next questions are still in the realm of small-talk that you could ask anyone. This means your future boyfriend will feel comfortable enough to answer without feeling exposed or vulnerable. However, they will still help you dive deeper into that beautiful, bewitching mind of his.

• Which fictional character have you found to be the most similar to yourself?

  He may answer this in a humorous way, which tells you a bit about him as a person – in a good way. After you’ve stopped laughing, try and steer him towards a more serious answer. The best way to figure somebody out is by understanding how they see themselves. This is a difficult thing to put into words. But everybody relates to a fictional character in a movie or book in some way, shape, or form. Get your crush thinking about this topic, and maybe you’ll see them in a new light.

• What do you hope to achieve in your life?

  This is a question I personally love to ask my crushes. It is always interesting to see their aspirations as a child and where they ended up as they got older. You never know; you may inspire them to reach for those goals more than they do already.

• If you could put a celebrity’s brain in another celebrity’s body, who would they be?

  This is a fun and quirky question, and it also reveals a lot about his “type”. Is he more into brains or beauty? What does he find attractive in a person? Does he value kindness over sex appeal? Maybe he can create a person who has everything and keep you guessing. Think about who you would mix and match too. It’s quite fun.

Most people love to talk about themselves, and it’s probably the same for your crush. Ask questions about his hobbies, job, and favorite sports in order to keep the conversation flowing. Most importantly, be responsive and relevant in your replies. By asking the following questions, the conversation will eventually flow like a raging river.

• How much do you hate your job?

  Why does everyone ask, “do you like your job?” The majority of people in this world are miserable in their line of work. This is a funny spin on a stereotypical question. From here, you can ask him what he would rather be doing and what he has done in the past. This topic is an awesome way to get a guy talking about his aspirations while texting.

• Where is one place you want to go in the world?

  This question will help you discover what your crush thinks about other cultures. Do they prefer the hustle and bustle of a city, or if they would feel more at home in nature. You can also find out if they prefer to lounge around or spend time out and about in the world. This is a pleasant conversation over text. Their answers will tell you a lot about compatibility. Can you imagine going traveling with this man? Wouldn't that be dreamy?

We have only scraped the surface when it comes to conversation starters, but there are literally millions of subjects to talk about with your crush via text. With a little bit of prep, you’ll be having meaningful conversations with that cute guy in no time at all!

• Cool Nicknames For Women
• How To Tell If A Guy Likes You Body Language
• Signals A Shy Guy Likes You
• How To Be A Good Kisser Guys
• The Opposite of Alpha Male