Things To Talk About With A Guy: Questions And Conversation Starters

Knowing what to talk about with a guy can feel challenging, whether you're on a first date, texting someone new, or trying to deepen an existing connection. Many people worry about awkward silences or putting too much pressure on themselves to say something interesting. Exploring ready-to-use icebreakers, deeper questions, text-friendly topics, and tips for building conversational confidence may help you feel more prepared. In many cases, genuine curiosity matters far more than the perfect opening line.

Tips for building confidence in conversations

Effective communication can seem like an elusive skill to master, which may cause many people to feel uncomfortable, nervous, or embarrassed when they attempt to start conversations with others. This may especially be true for young people, introverts, or individuals who experience social anxiety. If you have trouble projecting confidence when talking to other people, it can help to remember to be yourself. Most people appreciate authenticity and honesty, so consider letting the guy you're speaking with see the real you.

Also, mindfulness and active listening are skills that may help you communicate effectively, no matter the situation. Mindfulness is the ability to stay present and foster awareness of your thoughts, feelings, and surroundings. Active listening means devoting your full attention when the other person is speaking, trying not to interrupt or think about what you're going to say and instead waiting until they're finished before responding.

Here are a few approaches related to these two skills that may help you feel more at ease:

• Take a few deep breaths before you start a conversation to help settle any nerves.
• For in-person conversations, maintain eye contact and an open posture, which can help engage your conversation partner.
• Use your surroundings to come up with a topic if you experience an uncomfortable silence.
• Try summing up the other person's main points or asking a follow-up question to show you're listening.
• Consider joking about awkward silences to lighten the mood by addressing the subject directly.

Having a few conversation topics ready to go can also boost your confidence, so let's explore some icebreakers you can turn to next time you strike up a conversation.

Icebreakers and conversation starters to use with a guy

For many people, the hardest part of the conversation is the beginning. When you're approaching someone new, having a shared context can be so helpful, giving you something to talk about even before you know each other well. The icebreakers below may help the next time you speak to a guy you're interested in.

Comment on your shared environment

Part of the reason it can be difficult to talk with a stranger is that you might not know much about them yet. If you have nothing else in common, at least you're in the same place and can chat about that to start. A few examples depending on where you are:

• At a live music show: Consider asking how he first heard the band.
• At a coffee shop: You might ask what he usually orders or comment on the atmosphere.
• In a bar: You can ask if he's celebrating something or just out with friends.
• At the gym: You might ask if he has a favorite piece of equipment or a workout routine.
• At a party: You can find out how he knows the host.

Ask about his interests and hobbies

Many people enjoy talking about their passions and hobbies. Asking a guy what he does for fun may tell you a lot about him and give him a chance to talk about a topic that excites him. Consider a few questions like these:

• "What do you like to do on weekends?"
• "What's a hobby you've been wanting to try?"
• "Do you have any hobbies you're really into right now?"
• "What's your favorite way to spend a free afternoon?"
• "Is there a skill you'd love to learn someday?"

Share a story or ask for one

Sometimes, the best way to get over the awkwardness of starting a conversation is to dive right in. If you've got a funny, interesting, or unusual story, you might choose to open with that, using a direct, playful line such as, "The strangest thing happened today, and I feel like I need to tell somebody about it."

You can also find out whether he's up for sharing a story of his own by asking questions like, "What's the wildest thing you've ever done?" or "What's the most awkward moment you've ever experienced?" or "What's a story your friends always ask you to tell?"

Give a genuine compliment

If you've approached a guy you don't know, it might be because you think he's attractive. Have you considered telling him that? Your compliment may sometimes be a bridge to more substantial topics. You could tell him he reminds you of a handsome actor, then ask about movies he's seen. Or, you could say that his shirt looks good on him to start him talking about his fashion sense and personal preferences.

Fun and playful questions to ask a guy

Keeping things light can take some of the pressure off and make a conversation more enjoyable for both of you. If you'd like to keep the mood playful, consider a few of these questions.

Questions to ask a guy over text

Texting can feel different from talking in person, since it often gives you more time to think about your response and a little less pressure to reply right away. The right questions can keep a text conversation flowing without feeling forced. Here are some text-friendly options that may work well in written form:

1. What's been the highlight of your week so far?
2. What are you watching or listening to these days?
3. What's something that made you laugh recently?
4. If you had a free day tomorrow, how would you spend it?
5. What's a place you'd love to travel to next?
6. What's your idea of a perfect weekend?
7. What's something you're looking forward to?
8. What's a small thing that always puts you in a good mood?
9. What's the best meal you've had lately?
10. What's something you've been thinking about a lot recently?

Flirty questions to show romantic interest

Showing romantic interest can feel a little vulnerable, and that can be completely normal. If you're comfortable turning up the warmth, a few playful but respectful questions can help signal how you feel. Keep in mind that everyone's comfort level is different, so it can help to read his cues along the way and adjust accordingly if needed.

1. What's your idea of a perfect date?
2. What first attracted you to me?
3. What's something that instantly makes you like someone?
4. What's your favorite way to spend time with someone you care about?
5. What's the most romantic thing you've ever done?
6. What makes you feel most appreciated in a relationship?
7. What's a small gesture that means a lot to you?

Topics to get a guy talking about himself

Once you're past the introductions, certain topics can encourage a guy to open up a bit more and take the conversation further. The categories below may help you find a topic he enjoys.

His career and work life

If you express interest in what he does for a living, there might be a chance he'd want to discuss it further. Learning about his job can also lead to a discussion about his passions, his education, and his dreams for the future. Not sure where to start? It may help to ask questions like:

• "What do you enjoy most about that?"
• "How did you first get interested in that?"
• "Do you see yourself staying in that career?"
• "Can you describe a typical workday for you?"

Movies, TV, and entertainment

Entertainment can be a favorite topic of conversation for people of any gender. A simple way to learn more about a guy is to mention a recent movie or show you liked and ask if he's seen it. Even if the answer is no, this question can open the door to asking about media he has watched. You might also ask, "What's a show you could rewatch any time?" or "Is there a movie that really stuck with you?"

Music and concerts

A person's taste in music may sometimes reveal something about their personality or preferences in other areas. You don't have to limit yourself to asking about bands he's into, either. Sometimes, you can spark a more interesting conversation by asking something more specific, such as, "What's the first concert you attended?" or "What songs do you like to put on when you're driving?" Feel free to add in your own real-life anecdotes and experiences for a more engaging conversation.

His background and where he's from

It might not feel very original to ask, "Are you from around here?" But learning where a person came from and how they got here can be important for understanding who they are. If he moved from far away, chances are there's an interesting reason why. You can also find out more about his upbringing by asking about his favorite memory from childhood, his favorite subject in school, or what advice he would give his younger self if he could go back in time.

Deeper questions to build emotional connection

If you're interested in developing a deeper emotional connection with a guy, more profound topics may help, though these often work better once you've built some rapport. Psychologist Arthur Aron experimented with creating romantic bonds through short interactions that involved asking increasingly intimate questions, and reportedly, two of the study participants wound up getting married. Learning to guide a meaningful conversation is a skill you may be able to strengthen over time, and building communication skills through practice or support can help it feel more natural.

Questions about values and gratitude

What someone values most can reveal a great deal about who they are and what shapes their life. Consider a few of these questions when you're ready to go a bit deeper:

1. What in your life makes you feel most grateful?
2. Who has had the biggest influence on the person you've become?
3. What does a good life mean to you?
4. What values did you grow up with that you kept?
5. What's something you're proud of that most people don't know about?

Questions about dreams and the future

Talking about the future can help you glean insights about a guy and signal that you're interested in forming a more meaningful bond. These questions can reveal his goals, hopes, and the kind of life he imagines for himself:

1. Where do you see yourself in five years?
2. Imagine you could spend a week in any vacation destination with your best friends. Where would you go?
3. What does a meaningful life look like to you?
4. What's one big goal you're working toward right now?
5. If money weren't a concern, what would you spend your time doing?
6. Where would you most like to live someday?
7. What's something you hope to accomplish in the next few years?

Hypothetical questions that reveal character

Imaginative scenarios can touch on deep-seated values and personal histories in a way that feels playful rather than heavy. A few to consider:

1. If you could magically learn the truth about one thing, what would it be?
2. Imagine your house is burning down and everyone is safe. What one item would you save, and why?
3. If you could have dinner with anyone, living or deceased, who would it be?
4. If you could change one thing about the world, what would it be?

Once you've spent some time exploring these deeper topics, it can also help to know which subjects might be worth saving for later.

Topics that may be worth avoiding early on

When you're just getting to know someone, some topics may be better saved for once you've built more rapport. It can help to hold off on highly controversial subjects, detailed questions about past relationships, and overly personal questions before you both feel comfortable. These conversations may develop naturally over time, so consider reading his comfort level and taking things at a pace that feels good for both of you.

How online therapy can help with conversational confidence

Does the thought of bringing up these topics with a guy you like still make you break out in a cold sweat? Sometimes the real challenge isn't knowing what to say, but having the confidence to say it. Online therapy can offer a supportive space to practice communication skills, work through social anxiety, and build confidence from the comfort of home. With web-based platforms like BetterHelp, you can connect with a therapist through live chat, phone call, or video call, choosing the form of engagement that feels most comfortable to you.

Some providers on BetterHelp may be in-network with certain health plans, and co-pays average about $23/session for eligible members. Coverage varies by plan, provider, and therapist availability, so it can help to check your in-network status on the BetterHelp site. BetterHelp is working with insurance carriers to expand coverage across the United States, and in the meantime, the flexible subscription model continues to be an option to receive quality care from an extensive therapist network, with the cost of online therapy ranging from $70 to $100 per week, billed weekly or monthly, based on your location, referral source, preferences, any applicable discounts, and therapist availability. Note that any discounts apply to non-insured members only.

For those who may benefit from additional support, BetterHelp now offers psychiatry services through Uplift as an additional care option available alongside therapy, which may include medication management when clinically appropriate and based on a full clinical evaluation by a licensed psychiatric provider. Not everyone needs or benefits from medication, and any prescribing decisions are personalized.

Medication availability and coverage may vary by member location, clinical appropriateness, and individual pharmacy/insurance benefits. Prescribing decisions are made by the treating clinicians. We do not guarantee that any specific medication will be prescribed or covered by a member's insurance plan.

What the research says about online therapy

Most research studies on the topic report that online therapy can often be similarly effective to in-person therapy for addressing common mental health concerns. One study published in the European Journal of Public Health reports that internet-based therapy interventions can "successfully reduce symptoms" and are considered "efficacious treatments" in many cases. Plus, platform-specific statistics from 2024 report that 82% of BetterHelp users were likely to recommend their therapist to others.