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20 questions for dating — on apps and IRL 

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Jul 28, 2023

20 questions for dating — on apps and IRL 
  • Queer people meet, date, and fall in love in such beautifully varied ways, and dating is a way we get to experience our culture. It’s awesome and magical, and we have so much to learn about ourselves just from getting out there.

    So ask questions. A lot of them. And follow up with more questions. And listen. And do it because you genuinely care. 

    You’ve probably heard of “The 36 Questions That Lead to Love” from The New York Times, and there is something very appealing about a process that could make someone fall in love with you. But it’s also about how you ask questions. Does it feel like you’re reading off a list from The New York Times? Are you listening and responding? Are your responses making the other person feel uplifted or shot down like you’re trying to trick them? 

    Research shows that asking questions accomplishes two main goals of dating: learning about each other and setting a good impression. In a study from Harvard Business School, participants who went on speed dates and were instructed to ask many questions were much more likely to be offered a second date than their counterparts who were told to ask fewer questions. 

    Approaching dating with a spirit of curiosity alleviates some of the pressure of finding the right person and sets the tone that you care about another person. So ask, and you shall receive! 

    Getting to know people on dating apps

    Dating apps have introduced a new stage of question-asking before you meet in person for the first time. 

    Surveying my friends and sometimes maintaining a conversation on the apps can feel like a chore.

    Annie Lord, a Vogue columnist and author of Notes on Heartbreak, argues that apps themselves can make dating difficult. “They give you so many options. They have no connection to your social circle, so disappearing is easier.”

    The fear of ghosting, the repetitiveness of dating, and the addictiveness of swiping add new anxieties to conversations via text, which already lack many cues that we all rely on to engage with each other in person. 

    Apps like Her are tools — not a panacea to love or relationships. It’s important to approach the apps with realistic expectations and an understanding of what you want. One of the benefits of the apps — you can learn some basic information about a person to determine what you have in common. This is where asking a variety of questions — some simple, some silly, some serious — comes in. 

    Here are some questions to get things started on the apps. 

    Ask about their favorite things! 

    Favorite book, favorite movie, favorite TV show, favorite snack, favorite class in school, favorite song to sing in karaoke, favorite breakfast food, favorite flower, favorite sunset. 

    Life is filled with simple pleasures, and simply asking about them is the easiest way to learn fun facts about a new person, find out what they are passionate about, discover shared interests, and see what they find meaningful. 

    Ask about their day 

    This is one thing that keeps me coming back to dating — having someone to talk to about the silly little parts of everyday life. The beauty of the question “How was your day” is that it can be as simple or serious as the person wants it to be, and it’s a small gesture of care that you’re tracking someone in this big, lonely world. 

    Master the follow-up question 

    If you take anything from this article, remember that follow-up questions are your best friend. Alison Wood Brooks, a professor at Harvard Business School, has dedicated her research to the art of asking questions. One of her main findings: follow-up questions have a special power, making your partner feel respected and heard. They also don’t require preparation. Follow-up questions not only keep the conversation going on the apps — but they also show you are listening and that you care. 

    10 questions to bring to a first date

    So you made it off the apps, and now, in addition to picking an outfit, determining the time you should leave, and texting a friend for a backup plan, you have to face the prospect of making conversation IRL with someone you’ve met online. Don’t panic — it’s been done before. 

    I have been lucky to find a couple of long-term relationships from apps, and transitioning to the “real world” isn’t always easy. But coming prepared with questions and an eagerness to learn about a new person is a great way to start. 

    First, the good news: if you’re here on Her-dot-com, you hopefully don’t have to suffer through a first date with a heterosexual cis man. Congratulations! You are already on a path to meet someone with some basic decorum. But also shout out to the many straight men who are out here dating queer folks (hey, dad!). 

    According to psychologist Susan Krauss Whitbourne, people often express anxiety over hitting the right note between asking questions that feel too trite or too invasive. That makes a lot of sense! But you probably know from experience that it feels good to have someone express interest in your thoughts and feelings, and it does not feel good to go on a date where they ask you nothing. So even if your questions don’t always land, it’s still better to ask. 

    Here are some questions to get you started when you meet someone in person.:

    • Would you want to be famous? In what way? (From the 36 questions)
    • Before making a telephone call, do you rehearse what you’re going to say? Why? (From the 36 questions)
    • When you tell people where you’re from, do you think it surprises them?
    • How would you spend your time if you didn’t have to work?
    • What’s a place you want to visit?
    • When was the last time you cried?
    • Who are the series regulars in your life right now? 
    • What are your favorite things to do here?
    • Who do you go to for advice?
    • How do you wind down at the end of the day?

    6 questions to know where a relationship is going 

    As you continue seeing someone, you might find yourself once again wrecked with anxiety over yet another list of questions. When does it end? 

    Having intentional conversations only gets more important as you start setting the foundation of a relationship.

    Kaylee Rose Friedman, a sex therapist and relationship expert, said she looks to non-monogamous relationships to understand how to ask deep questions. “There’s a lot of assumptions rather than intentional conversations [in monogamous relationships.]…I want to help people be curious about what they really want based on their values and what works for each person.” 

    In any type of relationship, including with family or friends, you never stop asking questions. Intimacy requires this vulnerability to put yourself on the line with hard questions and return with the truth.  It isn’t easy, but with trust, it also isn’t always hard. And the payoff is worth it.  

    • What are you looking for right now?
    • Are you interested in monogamy, and what does that mean to you? 
    • Are you looking for a long-term relationship? What does that mean to you?
    • How much time together vs. apart do you need?
    • Are there sexual experiences you’d like to have that we haven’t tried yet?
    • What makes you feel cared for?
    • What does a healthy relationship look like to you?

    Asking questions and sharing about yourself is the start of opening up to let someone get to know you and accept you as you are. Why is it so scary? Humans are complicated. 

    Desire, love, and rejection are intertwined with how we see ourselves and the world. But asking questions is how we start to untangle all of that and find a deeper truth in ourselves. 

    All those anxieties, hopes, and fears are also swirling inside the person you’re trying to get to know. It’s about recognizing one another as real!

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    Catherine Henderson is a journalist based in Chicago. She has worked at a wide variety of newsrooms, including The Denver Post, Chalkbeat, Business Insider and In These Times, covering education, career development and culture. Catherine holds a master’s and bachelor’s degree in journalism from Northwestern University. Outside of work, she enjoys traveling, exploring Chicago, reading LGBTQ lit, and analyzing internet trends.

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