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Are you worried about running out of things to talk about with your BF? It can be tough to come up with fun, fresh, and interesting conversations on the fly, especially if you just started dating. Not to worry—we’ve got you covered. Read on for plenty of intriguing conversation starters that will keep your future phone calls unique and interesting.

1

Personal questions

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  1. [1] In one particular study, experts invited strangers to ask each other different sets of probing, personal questions. Try asking a few of these questions to your boyfriend and comparing your answers afterward. You might be surprised at how much closer you feel at the end of your phone call! Here are a few Qs to get you started: [2]
    • What are 3 things that both of us have in common?
    • Is there something you really want to accomplish? Why haven’t you done it yet?
    • What does friendship mean to you?
    • What topics are too serious to be joked about?
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2

Check-ins

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  1. Try changing things up by asking a more open-ended question. Instead of answering with a 1-word response, invite your BF to go into way more detail about how his day went. Then, do a switcheroo and share some interesting tidbits about your day. Try asking something like: [3]
    • What was the biggest highlight of your day?
    • What’s the most exciting thing happening at your job right now?
    • What’s the worst thing that happened today?
3

Hypotheticals

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  1. Pick his brain about anything and everything, from his desert island survival kit to his lottery spending plans. You can even add a philosophical touch with a celebrity dinner party question. Then, take an even deeper dive and ask him to explain why he feels that way. Here are a few ideas to get you going: [4]
    • What advice would you give your 10-year old self?
    • If you could wake up tomorrow with a new superpower, what would it be?
    • If you had the entire day to yourself, what would you do?
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4

Would you rather questions

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  1. In the best-case scenario, you can discover some new things that you have in common with your beau. In the worst-case scenario, you can transform your disagreement into a playful debate! Instead of giving a 1-word answer, take some time to explain why you prefer one thing over the other. Who knows—your friendly discussion could lead to a really fun, interesting conversation! Here are a few ideas:
    • Would you rather have every meal you eat be a little too spicy or a little too salty?
    • Would you rather talk to animals or speak every language known to humankind?
    • Would you rather have a high salary and a lot of debt or a low salary with absolutely no debt?
    • Would you rather go a week without showering or a week without brushing your teeth?
5

Bucket lists

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  1. Ask your boyfriend what he’d most like to do, such as traveling to Hawaii, going on a cross-country road trip, or skydiving. [5] Then, share your own bucket list, and see what dreams and goals you both have in common. You could ask: [6]
    • What’s on the top of your bucket list right now?
    • If you could travel anywhere in the world, where would it be?
    • What do you want to accomplish the most?
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7

Childhood memories

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  1. You can make this a serious discussion or keep it light-hearted—it’s totally up to you! Ask your beau what really keeps him up at night, or offer up a fear of your own to keep the conversation going. You might have more in common than you think. Try asking something like: [9]
    • What’s your biggest fear?
    • What’s a silly thing that you’re really afraid of?
    John Gottman, World-Couples Therapist

    When superficial small talk no longer suffices, explore purposeful questions that reveal your inner worlds instead. What hopes, values, dreams and even fears shape your partner? Where have they struggled and what lessons emerged? Conversation unlocks intimacy. Be fully present, listen without judgment and vulnerably share in kind. An amazing new depth emerges in relationships when making space for open, heart-centered communication.

9

Embarrassing moments

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10

Moments of gratitude

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  1. [12] Give your BF some to talk about what he’s most passionate about, and what he’d love to accomplish in the next few years and decades. Offer plenty of encouraging words, and remind him that you’ll always be there to support him along the way. Then, share some of your own hopes and dreams so he feels a little less vulnerable. For instance, you might ask: [13]
    • What’s your biggest goal right now?
    • What do you want to accomplish in the future?
    • Where do you see yourself in 10 years?
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Expert Q&A

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  • Question
    How do you keep a conversation going with your boyfriend on the phone?
    Shana Tibi
    Certified Professional Matchmaker
    Shana Tibi is a Certified Professional Matchmaker, Date and Relationship Coach, and the Founder of Curated Connections, a matchmaking service for single professionals. Shana specializes in understanding core values and personal preferences to curate dates. She holds a BA in Peace Studies and Conflict Resolution from Prescott College and an MSW in Social Work from California State University, Hayward. She is an active member of the Global Love Institute where she earned her matchmaking certifications.
    Certified Professional Matchmaker
    Expert Answer
    Try talking about things you have in common! Shared experiences make for great conversational topics, whether it's books, TV, entertainment, or music. You could even chat about a hobby you both enjoy, like cooking.
  • Question
    How do I start a deep conversation with my boyfriend?
    Shana Tibi
    Certified Professional Matchmaker
    Shana Tibi is a Certified Professional Matchmaker, Date and Relationship Coach, and the Founder of Curated Connections, a matchmaking service for single professionals. Shana specializes in understanding core values and personal preferences to curate dates. She holds a BA in Peace Studies and Conflict Resolution from Prescott College and an MSW in Social Work from California State University, Hayward. She is an active member of the Global Love Institute where she earned her matchmaking certifications.
    Certified Professional Matchmaker
    Expert Answer
    Bring up some long-term, serious topics. You might chat about your core values, your 5-year plans, your money management strategies, or even your plans to have a family. Keep in mind that these topics are better to talk about if you're in a serious relationship.
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