This article was co-authored by Shana Tibi
and by wikiHow staff writer, Annabelle Reyes
. 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.
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Are you worried about running out of things to talk about with your boyfriend over the phone? It can be tough to come up with fun, fresh, and interesting conversation topics 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 with your boyfriend interesting and fun!
Things to Talk about with Your Boyfriend
- What’s your favorite movie?
- If you could have any superpower, what would you pick?
- What is your most treasured memory?
- What do you think your love language is?
- What never fails to make you laugh?
- What’s your favorite way to spend a Sunday?
- Do you have any guilty pleasures?
Steps
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Ask your boyfriend some personal questions to bring you closer together. Research shows that engaging in “reciprocal self-disclosure” (sharing personal information with each other) dramatically increases feelings of closeness and intimacy. [1] X Research source Try asking your boyfriend a few questions about his thoughts, beliefs, and passions, and share your perspective as well. 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:
- What are 3 things that you think the 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?
- What do you feel most grateful for in your life?
- If you had to list your top 3 core values, what would they be?
- Do you consider yourself more of an introvert or extrovert?
- Which of your personal qualities are you most proud of?
- How would you describe your communication style?
- Do you forgive easily, or do you tend to hold grudges?
- How do you cheer yourself up when you’re sad?
- If you had to plan the perfect day, what would it look like? [2] X Trustworthy Source Greater Good in Action An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life Go to source
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Generic questions like “how are you” don’t accomplish much. Instead, try changing things up by asking a more specific, intentional question about how he’s doing. These types of questions invite your BF to go into way more detail about his day or week, instead of giving a quick “I’m fine,” or “I’m doing well” as a response. [3] X Research source After he gives his answer, do a switcheroo and share some interesting tidbits about your day. Try asking something like:
- What was the biggest highlight of your day today?
- What’s the most exciting thing happening at your job right now?
- What has been the highest point and the lowest point of your week so far?
- Are you learning anything super interesting in your classes right now?
- If you had to describe your day in one word, what would it be, and why?
- What was one thing that really surprised you this week?
- What are some of the things going on in your life right now that inspire or energize you?
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Fun, made-up scenarios are the perfect way to keep your conversation going. 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] X Research source
- If you could go back in time and give advice to your past self, what would you say?
- If you could wake up tomorrow with a new superpower, what would it be?
- If you could invite 5 people, living or dead, to a dinner party, who would you pick?
- If you won the lottery tomorrow, what’s the first thing you would buy?
- If you only had one day left to live, how would you spend it?
- If you could live in any city in the world, what city would you pick?
- If you could get free food from any restaurant for the rest of your life, which one would you choose?
- If you could live in a fictional world from a movie, show, or book, which one would you choose?
- If someone was making a movie about your life, what actor would you want to play you?
- If you could only watch one movie for the rest of your life, which one would it be?
- If you could only bring three things to a desert island, what would they be?
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Ask him about the art and entertainment he enjoys. If you want to keep the conversation light and fun, professional matchmaker Shana Tibi suggests asking about his favorite books, TV, songs, and other types of entertainment. [5] X Expert Source Shana Tibi
Certified Professional Matchmaker Expert Interview. 19 October 2021. You may find that you share a lot of interests, which can open doors to fun date nights, like seeing an artist you both like in concert, or having a movie night watching a film you both enjoy. Here are some favorites questions to ask:- What’s your favorite movie?
- What’s your favorite film genre?
- Who’s your favorite director?
- Who’s your favorite actor?
- Who’s your favorite musician?
- What’s your favorite band?
- What’s your favorite album?
- What’s your favorite song?
- What’s your favorite TV show?
- What’s your favorite book?
- Who’s your favorite author?
- Who’s your favorite fictional character?
- What’s your favorite sport to watch on TV?
- Who’s your favorite athlete?
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Everyone loves a classic “Coke or Pepsi” question. 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 fun would you rather questions to get you started:
- 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?
- Would you rather be able to teleport anywhere in the world, or travel through time?
- Would you rather have a five minute conversation with your past self or future self?
- Would you rather never be able to listen to music again, or never be able to watch a movie again?
- Would you rather be able to play every instrument in the world, or be able to play every sport in the world?
- Would you rather be stuck on a spaceship or stuck on a boat in the middle of the ocean?
- Would you rather have to eat breakfast foods or dinner foods for every meal?
- Would you rather always be overdressed or always be underdressed?
- Would you rather have summer last the whole year, or have winter last the whole year?
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Bucket lists are a creative way to keep your conversation going. Ask your boyfriend what he’d most like to do, such as traveling to Hawaii, going on a cross-country road trip, or skydiving. Then, share your own bucket list , and see what dreams and goals you both have in common. You could ask: [6] X Research source
- What’s at the top of your bucket list right now?
- What are five things you want to make sure you do before you die?
- What are your top three cities that you’re dying to travel to?
- What strange or wacky foods do you want to try in your lifetime?
- What adventurous or dangerous activities do you want do at some point in life?
- What musicians do you want to make sure you see in concert before you die?
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Take a trip down memory lane and ask about the time he first saw you. Was it love at first sight, or did it take some time for sparks to start flying? Keep the conversation going by sharing your side of the story, too. It can be super interesting to talk about your different perspectives of the same event! You might ask him: [7] X Trustworthy Source Harvard Medical School Harvard Medical School's Educational Site for the Public Go to source
- What did you think of me when we first met?
- Did you always want to date me, or were you interested in someone else?
- Did you feel chemistry the first time we met, or did it grow later?
- What was the first thing you noticed about my physical appearance when we met?
- What did you like best about my personality after our first meeting?
- Now that you know me better, does your first impression line up with the way you see me now?
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Relive some iconic moments from your childhoods. Ask your BF to think about his most vivid childhood memory, or invite him to tell you about one of his favorite childhood adventures. Then, you can trade stories and see how similar or different you were as little kids. Try asking: [8] X Trustworthy Source Harvard Medical School Harvard Medical School's Educational Site for the Public Go to source
- What is your earliest memory from childhood?
- What is your most treasured memory from childhood?
- What was your best friend like when you were growing up?
- What was the most adventurous thing you did as a kid?
- What was the worst trouble you ever got into as a child?
- Did you have any special family traditions when you were younger?
- Which family member were you closest to when you were growing up?
- Are you happy with the way your parents raised you? Would you change anything about it?
- What was your favorite activity or game to play when you were little?
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Compare notes on some of your biggest fears. 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] X Research source
- What’s your biggest fear?
- What were you most afraid of when you were little? Is it different from what you’re most afraid of now?
- What’s a silly thing that you’re really afraid of?
- What fictional movies or characters scare you the most?
- Are you afraid of any animals, like spiders or snakes?
- Do you believe in ghosts or the supernatural, and if so, do they scare you?
John Gottman, World-Couples TherapistWhen 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.
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Bust out the laughs with some of your most infamous, noteworthy tales. Ask him to share an embarrassing tale from his past, or get the ball rolling with your own story. To really up the ante, try competing to see who has the most cringe-worthy tale to tell! Let your conversation grow a silly, hilarious life of its own as you continue to rehash some of your most humiliating moments together. Here are some ideas to get you going: [10] X Research source
- Do you have any embarrassing summer camp stories?
- What’s something that your family never lets you live down?
- Did your parents ever embarrass you on purpose in front of your friends?
- Did you have any embarrassing or silly nicknames when you were little?
- What’s the most embarrassing moment you ever had at school?
- Have you ever put your foot in your mouth during an important conversation?
- What’s your most cringe-worthy first date story?
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Think about what you’re both really thankful for. Talking about gratitude may seem pretty sappy, but it’s actually the perfect way to keep your phone conversation going. You’ll get to learn more about the most important things in his life and what he values, and maybe even hear how much he appreciates you. Then, take your chat in a new direction by sharing what you’re grateful for. You could ask: [11] X Research source
- Who has had the biggest, most positive impact on your life?
- Which family member are you most grateful for?
- Which of your friends has made a positive difference in your life lately?
- What’s something I do that you’re grateful for?
- What is a physical object, hobby, or experience that you’re really thankful for right now?
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Ask your boyfriend about his goals and dreams. If things between you are starting to get more serious, Tibi recommends asking about his plans for the future, and what he wants out of life. These types of questions can lead to some great conversations , and they can also help you make sure that you’re “heading in the same direction for a long-lasting, meaningful relationship." [12] X Expert Source Shana Tibi
Certified Professional Matchmaker Expert Interview. 19 October 2021. You can also share some of your own hopes and dreams so he feels a little less vulnerable. Here are some questions to ask: [13] X Research source- What’s your biggest goal right now?
- What do you want to accomplish in the next 5 years?
- When you picture your life in 10 years, what does it look like?
- What are some short-term career goals you want to go after this year?
- What is your dream career, and do you feel like you’re on track to achieve it?
Expert Q&A
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QuestionHow do you keep a conversation going with your boyfriend on the phone?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.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.Thanks! We're glad this was helpful.
Thank you for your feedback.
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QuestionHow do I start a deep conversation with my boyfriend?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.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.Thanks! We're glad this was helpful.
Thank you for your feedback.
If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
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References
- ↑ https://journals.sagepub.com/doi/pdf/10.1177/0146167297234003
- ↑ https://ggia.berkeley.edu/practice/36_questions_for_increasing_closeness
- ↑ https://www.forbes.com/sites/amberjohnson-jimludema/2018/04/05/five-questions-you-can-ask-instead-of-how-are-you/
- ↑ https://psychcentral.com/relationships/creative-curious-questions-to-deepen-your-connection-with-your-partner
- ↑ Shana Tibi. Certified Professional Matchmaker. Expert Interview. 19 October 2021.
- ↑ https://www.psychologytoday.com/us/blog/click-here-happiness/202111/how-create-your-bucket-list
- ↑ https://www.health.harvard.edu/mind-and-mood/tips-to-retrieve-old-memories
- ↑ https://www.health.harvard.edu/mind-and-mood/tips-to-retrieve-old-memories
- ↑ https://psychcentral.com/health/dont-let-fear-destroy-your-relationship
- ↑ https://www.psychologytoday.com/intl/blog/fulfillment-at-any-age/202306/do-you-and-your-partner-laugh-at-the-same-things
- ↑ https://positivepsychology.com/gratitude-appreciation/
- ↑ Shana Tibi. Certified Professional Matchmaker. Expert Interview. 19 October 2021.
- ↑ https://psychcentral.com/blog/45-conversation-starters-to-bolster-your-bond-with-your-friends-and-family#4