21 Questions To Text Your Date To Keep The Conversation Going

Is there anything more satisfying than an effortless text convo with that cutie you’ve gone on a couple of grade-A dates with? Those easy-breezy back and forth exchanges stoke your excitement because they suggest a certain level of chemistry and compatibility that bodes well for your potential future. In the early stages, it’s easy to get a tad tongue-tied in your text convos — but maintaining that momentum is crucial. Fortunately, there are a number of questions to text your date to keep the conversation going.

Seeking tips for free-flowing text conversations? Questions are obviously the most effective way to inspire a response — but not just any questions. Whereas you can quickly hit a wall with yes or no questions, open-ended questions encourage a longer, more meaningful exchange. It’s also worth timing your texts thoughtfully, too. If you know your date’s work schedule, consider texting them when they’re more likely to respond, such as when they’ll be taking a lunch break or heading out of the office. Speaking of which, you can keep the convo flowing by texting them when you have time to engage (i.e., not right when you’re about to hop in the shower).

The right questions not only allow you to maintain interest in between dates, but they also offer an opportunity to get to know each other better. If you play your cards right during these text exchanges, you’ll have even more to talk about next time you meet up IRL. Sometimes, it can be challenging to strike a balance between topics that only skim the surface and ones that are too deep to ask over text. Not sure where to start? Here are some questions to keep the ball rolling.

The best questions to text your date to keep the conversation going are open-ended.
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1. “I’m looking to plan a trip this summer and could use some destination inspiration. Where have you traveled that really made an impact on you?”

2. “I think I’ve officially played every song on my workout playlist to death. What are your go-to jams right now?”

3. “Looking for something to watch RN and I’m feeling indecisive. Any recommendations?”

4. “Finally pouring a glass of wine after a long workday, hallelujah. How do you like to relax after a long day?”

5. “Looking through The Office memes on my lunch break. What was the highlight of your day today?”

6. “Fun fact: I’ve never done [insert activity]. Thoughts on trying that for our next date?”

7. “Which personality type are you? I’ve been reading a lot about Myers-Briggs lately, so I’m curious.”

8. “I meant to ask you the other night — do you consider yourself a night owl or a morning person? Fingers crossed we’re in the same boat.”

9. “I’ve been trying to develop a morning routine to start my day off on the right foot… do you have any daily habits or practices that you love?”

10. “What do you hate most about dating today? (I’m more than happy to share my take.)”

11. “Is there anything currently on your bucket list that we could cross off?”

The best questions to text your date to keep the conversation going aren't too shallow, but aren't too deep.
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12. “Grabbing my must-have morning coffee/tea RN… speaking of which, how do you get your daily caffeine fix?”

13. “What’s your favorite thing to cook? (Heads up, I will probably want to sample that at some point).”

14. “Hypothetically, if we were gonna crush a trivia night together, which topics would you absolutely dominate?”

15. “Confession time: I have an irrational fear of [XYZ]. So, what’s yours?”

16. “Where do you like to go when you’re just looking to kill some time? Asking for myself.”

17. “Is there anything you totally nerd out on? For me, it’s [XYZ].”

18. “Hey, do you have any nicknames I should know about? The weirder, the better.”

19. “If income wasn’t an issue and you could do anything for a living, what would you be doing right now?”

20. “Real talk. If you had to give up texting or Netflix for a week, which would it be?”

21. “OK, I’m starting an AMA. What’s one question you wish you asked me on our last date?”

 

Philadelphia, PA, USA

Author: phicklephilly

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