Talking to a guy for the first time can feel a little nervous, but it’s also a way to build a real connection and see how compatible you are. Choosing the right topics helps keep the conversation interesting, easy and natural. Here are 25 questions and ideas that will help you to get to know him - whether you are chatting online or meeting in person.
Conversation topics for texting
Messaging in a chat or on social media is a great way to learn more about him before your first date. If your conversations usually start in the morning, you can keep it simple and warm:
- How’s your morning? Did you dream anything?
- What’s on your agenda for today? Anything fun?
- What’s your favorite kind of breakfast?
- Coffee, tea of something else to start the day?
Even simple questions can turn into a great dialog. These topics will help you avoid one-word replies and keep the chat lively:
- Do you usually cook for yourself or prefer ordering in?
- What small things make your day better?
- Do you like creating things with your hands? Would you like to try sometime?
- What activities bring you the most joy?

What to talk about on a date?
Date is your change to get to know each other better. To learn more about him, ask questions that reveal his personality and values, but pay attention on his reactions and mimic. Unlike texting, in-person conversation lets you notice tone and body language.
Many guys enjoy remembering their childhood, it’s an easy warm topic that often brings out good memories. Try asking:
- Where did you grow up? What was you childhood like?
- Do you have any brothers or sisters?
Mix deeper questions with lighter ones. For example, about food and everyday favorites:
- What dishes do you like to cook?
- Do you have a favorite cafe or restaurant?
Keep the conversation going with open-ended questions:
- Do you like spending time outdoors?
- Do you play any sports?
- What do you like to do on the weekends?
Carrier is often a big part of like for many men, so it’s fine to ask about it, as long as the topic feels comfortable:
- What do you do for work?
- Do you have any goals or dreams related to you career?
If work isn’t something he’s passionate about at the moment, shift to more related topics, such as travel of leisure:
- What places do you dream of visiting?
- How do you like to spend you free time?

How to keep conversation going?
Sometime even the best conversation can hit a pause and that’s perfectly fine. If things feel awkward you can always move chat back on track.
Here are a few universal tips:
- Use what’s around you. Comment on the place you’re at or event you’re both attending.
- Avoid controversial topics. Politics, exes or money talk can wait.
- Ask open questions. Encourage him to share more that a simple yes or no.
- Don’t turn it into a interrogation. Keep things balanced and easygoing.
- Be open and genuine. Sharing a bit about yourself helps the conversation flow naturally.
- Use humor. A good laugh makes things more relaxed.
- Pay attention to his reactions. If a topic feels awkward or too personal, smoothly change the subject.
Want to make it easier?
Download AskCloser app - it includes ready-made sets of questions for any situation.
All the topics were developed with professional psychologists, so you’ll always find a way to connect and have a meaningful conversations with anyone.




