10 Clever Questions To Ask When You're Texting, Because "What's Up?" Isn't Cutting It

I'm definitely a strong advocate for texting. I even prefer it to talking on the phone or in person nine times out of 10. My words just come out better when I write them than when I try to speak them. But even though my love for texting runs deep, I can't deny the fact that sometimes, text convos can be boring. When you're trying to get to know someone, the same, "Hey, what's up?" conversations get old quick. But, I have good news for my fellow text-lovers. There are clever questions to ask when texting that can help you avoid the usual, plain, text conversations.

While, "Hey, what's up?" can lead to solid conversations about what's going on in your day, sometimes it just results in very simple conversations, especially at the beginning of a new relationship. Early on, you usually want to get to know as much about someone as possible. There's an endless fountain of cool things you could learn about a new person in your life, but sometimes that can be hard to do through text if you have the same few conversations over and over.

Next time you find your text conversation dying down when you really don't want it to, try asking one of these questions instead of, "Hey, what's up?"

1What's The One Superpower You'd Want? And What Would You Do With It?

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Honestly, I never know how to answer this question because there are three powers I would love to have: teleportation, invisibility, and the ability to read minds. I just can't pick one because I want all three! Superpowers can tell you a lot about someone, like what it is they value. But even if they don't reveal everything, it's still cool to see if the two of you have similar interests.

2Do You Have A Bracket For March Madness?

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My friend said she used this on a guy, and it got him talking like nothing else had. Even if you know absolutely nothing about basketball, a quick Google search should give you a good run-down. You can bring up the colleges playing, or any fan-favorite players to keep an eye on. If you aren't a basketball fan, consider bringing up a sport that you both like!

3What's Your Dream Place To Live?

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I've told myself time and time again that if I don't live in New York City one day, my life will never feel complete. I'm always curious to see if the person I may end up dating has that urge, too, about any city. By asking someone where they'd love to live, you can get a sense of how they feel toward their hometown. Maybe they're dying to get out, or they have a strong desire to live abroad that you wouldn't know abut otherwise. This question can give you a better understanding of who they are, overall, and it'll definitely prompt good conversation.

4What Color Do You Most Associate With?

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OK, this is kind of a weird question, and it might take some explaining, but it would be pretty cool to see what color someone associates with. Different colors mean different things. Red is the color of passion and drama. Orange is an encouraging color. Yellow is optimistic. Pink often signifies sensitivity just to name a few. If someone feels a connection to a color, it can give you a peak at the kind of person they are. You can call me Mellow Yellow.

5What Is The Most Interesting Thing You Have On You Or Near You Right Now?

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Beware, the answer to this question could get a little weird depending on who you're asking, but it's still an interesting thing to see. What if they're sitting next to their cat, who's snuggling up to their pet snake? That's totally something I would want to know.

6What's The Most Prized Possession In Your Wallet?

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Some people use their wallet strictly for money. Some like to include little trinkets or pictures, and others may just have lots of condoms. It varies. Something as simple as a wallet can speak wonders about someone. For example, if they have a picture of a loved one in their wallet, it can show their sweet side. If they use it just to keep their money in one place, it shows practicality. If they have a lot of condoms, you know they value safe sex, and that's always important!

7What's Your Favorite Go-To Pick-Up Line?

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Cheesy pick-up lines are my absolute favorite. I wouldn't want someone to try to pick me up with one, but I'd love to hear what they've used on other people that's actually worked. Someone's go-to pick-up line can give you a glimpse at their creativity and their sense of humor. And, even if it's the most basic pick-up line, like, "I seem to have lost my phone number. Can I have yours?" at least the two of you can LOL about it.

8If You Could Have Dinner With Anyone, Dead Or Alive, Who Would It Be, And Why?

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I struggle with my answer to this question. Sometimes, I'm sentimental and say my grandfather, but other times, I try to think of which celebrity I'd want to sit across from and just stare at.

Maybe you and the person you're texting want to have dinner with the same person, and it'll show you're a lot more alike than you would've thought. Maybe they want to sit down with someone you can't stand, and then you know to get out now. Regardless, it'll show you something.

9If Your Life Was A Movie, Which One Would You Want It To Be?

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OK, TBH, I'm super surprised I don't immediately have an answer for most of these questions. There are so many movies I'd love to jump right into! Definitely every other rom-com. Like, yes, please serenade me or organize a flash mob in the middle of the day. But also, being Wonder Woman would be incredible. So many choices! By asking the person you're texting what movie they wish their life would be like, it might help you see the things they want out of their actual lives.

10What's The First Memory You Have From Your Childhood?

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Whether your first memory is about the days you'd spend watching and rewatching the same movie, or it's playing in your pool as a toddler, everyone has that one thing they revert back to when reminiscing about their childhood. Asking someone what their first memory is can give you an insight into how they grew up that you otherwise may not get until further down the line.

Next time you're texting someone, and you want to have a real conversation, try switching it up from your usual, "What's up?" and ask one of these questions instead. They could lead to a conversation you might not have ever had to begin with, and those can often be the most interesting.

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