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Sex + Relationships

Questions and Conversation Starters to Help Not Sound Awkward During Your Next Virtual Date

During the months of quarantine stuck at home, there has been a surge of dating app use for those of us who are single. Everyone seems to be wanting to meet their “Quarantine Cutie” and replicate that adorable story of the couple who met in Brooklyn.  However, social distancing and quarantine guidelines have advised against meeting in person, so if you’re like me you’ve been doing the next best thing: virtual dates. 


Whether you’re using Netflix Party to catch up on Tiger King together, or if you’re flirting over Zoom, the conversation probably has gotten a little awkward at some point. You’re both nervous to be talking to someone new, and it’s hard to think of what to say on the fly. It’s especially nerve-wracking if you suffer from social anxiety like I do, where no matter how badly I want to talk to someone I often hold myself back from it, terrified I’ll come off as creepy and nosey. 


But thankfully I have access to the internet, and with a few Google searches and help from my Instagram followers, I found a pretty large group of interesting questions that help break the tension and create a conversation that’s fun and engaging and can help take the anxiety out of getting to know someone new. 


First, let’s start with some of my favorites from a SubReddit thread that seems to have all the answers for how to be pretty good at this whole dating thing (yes I use Reddit leave me alone the memes are funny). Whoever created and archived this post has my whole heart, thank you for sharing your wisdom. 


  1. Who are the 3 most important people in your life?

  2. What are you watching on Netflix right now? 

  3. What did you want to be when you were a child?. 

  4. What was the best part of this year?

  5. What is your dream career?

  6. Do you like tattoos?

  7. Who is your dream dinner guest dead or alive?

  8. Who is your favorite Disney villain?

  9. How do you like to spend your day? 

  10. Are you an introvert or an extrovert? 

sticky note that has \"Stay home\" written on it

Next let’s move on to some of my favorite questions from psychologist Arthur Aron’s study that talks about whether or not intimacy between two strangers can be accelerated by asking each other a series of personal questions. Some of these might be a bit intense for a first date but they can help you generate your own questions to ask your partner. 


  1. Before making a telephone call, do you ever rehearse what you’re going to say? Why?

  2. When did you last sing to yourself? 

  3. Do you have a secret hunch about how you will die? 

  4. If you could change anything about the way you were raised, what would it be?

  5. Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

  6. When did you last cry in front of another person? By yourself?

  7. What, if anything, is too serious to be joked about? 

  8. What is your most treasured memory? 

  9. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

  10. What does friendship mean to you?  

World closed sign
Edwin Hooper

Next, let’s look at a few questions from a website called Conversation Starters World that lists 160 questions for first dates because honestly you can never have enough get-to-know-you questions and conversation starters when you meet someone new. 


  1. Who is the most fascinating person you’ve ever met? 

  2. What is the last book you really got into?

  3. What amazing adventures have you been on?

  4. What are you kind of obsessed with these days?

  5. What is the most interesting fact you know? 

  6. How many siblings do you have?

  7. If there were an Olympics for everyday activities what activity would you win a medal in?

  8. Among your friends what are you best known for? 

  9. What are some accomplishments you’re really proud of?

  10. If you could give everyone one piece of advice what would it be? 

phone with social media displayed on screen
Erik Lucatero | Unsplash

And finally, let’s hear what my Instagram followers had to say on the matter! Follow me on Instagram (ag.dickerson) to be a part of the article the next time I do something like this! Special thank you to everyone who responded and made it into this article, you guys are the best. 


  • Chloe says: 

    • When it comes to classmates I have an interest in I ask about an assignment or start talking about the professor

  • Ana says:

    • If you had to be an animal what would it be and why?

  • Sami says: 

    • What is your spirit vegetable? 

  • Anastasia says: 

    • What’s your major/what did you study in college? 

    • What kind of movies do you like to watch?

    • Who did you vote for in the 2016 election?

  • Gabby says: 

    • What kind of music are you into? 

  • Leonie says: 

    • What countries have you been to? 

  • Cat says: 

    • What’s your favorite musical? 

    • What’s your major? 

  • Kayley says: 

    • I love asking white people about their family’s ethnic heritage

  • Sarah says: 

    • My go to is definitely asking about hobbies so I know about the activities that make them happy

  • Ashley says: 

    • What is something you wish more people knew about you? 

  • Jayla says: 

    • What’s the best thing that’s ever happened to you? 

  • Liz says:

    • At work, it’s always an over-enthusiastic “good morning how are you?” to stand out

  • Rasaaq says:

    • Its always fun to ask about their music taste

  • Jay says:

    • I like to ask if they play a musical instrument


Hopefully, these questions help you get out of your shell a little bit more, or even help you create get-to-know-you questions of your own! Good luck, stay safe, and have fun. 


Until next time, 


I am a public relations major with hopes to work for an agency PR firm one day. I love writing and I'm always on the hunt for new article ideas and I love collaborating with like-minded people! Find me on my listed social media and reach out with any questions or comments, I'm happy to talk to you!
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