Thinking of calling the guy you're interested in but unsure of what to say? Or perhaps you're wondering how to talk to the guy you're dating over the phone? Whether he's your crush or your boyfriend, knowing how to strike up a conversation can be tricky. Don't worry—this guide will provide you with fantastic conversation tips, so you can confidently make that call to the special guy in your life. You've got this!
This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.
Important Things to Consider
- Ask intriguing questions like, “What did you think of that assignment the other day?” or “What’s your all-time favorite movie?” to get the conversation going.
- Provide thoughtful responses and bring up new topics, such as, “Yes, that movie was amazing! I love comedies—what about you?”
- If you're feeling anxious, jot down a few topics or questions beforehand. That way, if you lose track of the conversation, you’ll have something to refer to.
Steps to Take
Talking to Your Crush

- Choose a comfortable, private spot, like your bedroom, to talk without interruptions. The more relaxed you are, the more confident you’ll feel.
- If you’ve been dropping hints that you like him, calling him is a great way to make it clear.

- Ask him things like, “How was baseball practice last night?” or “What’s your term paper about?” to get him talking about his passions. These open-ended questions encourage more than just a yes or no answer.
- Get flirty with a question like, “What’s your dream partner like? What qualities do you love?”
- Reader Poll: We asked 833 Mytour readers about the best conversation topics for talking to a crush, and 62% said hobbies and recent fun activities were their top picks. [Take Poll] So, according to our readers, asking him what he enjoys doing for fun is a foolproof option!

- If it’s his voicemail, stay calm and leave a simple message like, “Hey John, it’s Eve. I just wanted to see what you've been up to. Talk soon!”
- If you’re feeling playful, leave a silly message like, “If you don’t hear from me, I might have been abducted by aliens. Or I might just be out!”

- Avoid questions like “What’s up?” or “What’s your favorite color?”—they’re too vague and don’t leave much room for conversation.
- Examples of great questions: “I noticed your style is always on point. What inspires your fashion choices?” or “I saw you wearing a Steph Curry jersey. Are you a fan of the Warriors too? He’s one of my favorite players!”


Relationship Specialist
Use stories about bad first dates as a fun way to break the ice. Nearly everyone has experienced a terrible date or received strange messages online. Sharing these experiences can spark conversation while also highlighting that you're nothing like those awkward situations.

- Ensure you don’t interrupt him while he’s speaking, and wait for him to finish before you respond. Interrupting can come across as impolite, even if you're just trying to join in.

- Other great examples: “No, horror films aren’t really my thing, but I do enjoy a good thriller every now and then. What’s the scariest movie you’ve ever seen?” or “Yes, I love cooking! Pesto pasta is my go-to dish. What about you?”
- Giving detailed responses not only reveals more about you but also gives him opportunities to keep the conversation flowing.

- If you notice long pauses or feel like you're forcing the conversation, it’s probably time to end the call.
Talking to Your Boyfriend

- Once you start chatting, your nerves will likely melt away—it’s just the initial call that's a bit intimidating.

- Try asking, “How did that project you were working on last time go? It sounded so interesting!” or “Did you end up seeing that movie we talked about? How was it?”
- Remember, if you both struggle to find things to talk about, it doesn’t mean the relationship isn’t working—it might just mean you’re still getting to know each other.


Relationship Expert
Bring up something you’ve just experienced. For example, you could say, "I just got back from the gym" and then talk about your workout routine.

- If you’re not in the mood to make the first call, texting is a low-pressure option that could encourage him to reach out to you. Flirty texts like: “Wish you were here right now. What’s up?” or “Have you been thinking about me?”
- Talking on the phone about once a day, alongside texting, can usually help keep your relationship strong even when you're not physically together.

- “I’ve always been terrified of heights—I even get nervous climbing a ladder! What about you? What’s something that scares you?”
- “I’ve always dreamed of becoming an entrepreneur—it’s important to me to create something of my own. What’s your biggest goal in life?”

- For example, if your partner asks if they should reconnect with an old friend, a great response could be, “That’s such a wonderful idea! The hardest part is reaching out, but once you do, I’m sure it’ll feel like nothing’s changed.”

- “Soccer practice was such a blast today! By the way, who’s your favorite soccer player?”
- “I noticed you post a lot about art on your Instagram. I love going to museums! Do you have a favorite artist?”
- Get playful with, “I know we both enjoy a good time out. I’m curious—what would your ideal date be?”


Dating Coach
Shower him with compliments. When chatting with someone special on the phone, sprinkle in compliments like, "Your voice on the phone is like a melody to me." Be romantic and talk about things you’d love to do together. You can even share a story about something that made you think of him, creating a sweet moment of connection.

- Remember, a quiet moment doesn’t mean the call is going poorly. Silence often signifies comfort, showing you enjoy each other’s company and don’t always need words to fill the space.

- To keep things cheerful, leave with a compliment such as, “I wish more people were as easy to talk to as you. Wish me luck on my next shift—take care!” or “I don’t know why everyone doesn’t have your taste in restaurants! About to go to a terrible place with my friend, but hey, it’s her pick!”
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Don’t stress if the conversation doesn’t flow as smoothly as you hoped. You can always try again, or have a more relaxed conversation with someone else who you naturally connect with.
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Avoid eating, heavy breathing, or engaging with other people while on the phone. It can come across as if you’re not fully present or interested.