How to Start a Conversation With a Guy Confidently

woman flirting with young man

It's natural to be a little nervous, but don't panic if you're unsure how to start a conversation with a guy. It's actually much easier than you think. The best way to get the conversational ball rolling depends on whether you're talking in person, online, or over text. Once you understand the basics, you'll be able to form a connection quickly.

First Things First: Conversation Basics

Before you begin any conversation with a guy, it's important to remember that anything you say will fall into three main categories:

  • You - You can talk about some aspect of yourself, although this is probably the most difficult way to get a conversation started.
  • Him - You can make an observation or ask a question about him or something he is doing.
  • Your environment - This includes everything else around you in your shared environment.

Starting a Conversation in Person

Although it may seem daunting, starting a conversation with a guy in person may be one of the easiest ways to get the ball rolling. There's a lot you share in your environment, since you're physically together. Here's how you can use these commonalities to jump start your conversation.

couple drinking beer in pub

1. Notice Something in Your Environment That Affects Both of You

Take a moment to be mindful of what is going on around you. What are you both seeing, feeling, or tasting? These are shared experiences, which can give you something to talk about. This will be very specific to your situation, but here are some possible examples:

  • Food you're both eating
  • Music that's playing
  • A sunset or beautiful view that's right in front of you
  • Warm or cold weather
  • A show or movie you just watched
  • The host or hostess at a party
  • An exciting event that's about to happen

2. Make It Personal and Positive

Once you have a common topic from your environment, you need to make it personal. A simple observation about the weather isn't going to inspire him to continue chatting. Instead, you need to consider how this thing in your environment is affecting either or both of you. How do you feel about this thing? How is it impacting the two of you? In general, it's best to start with something positive too. Avoid negative remarks about people, food, music, and anything else. Here are some examples:

  • A band you've heard before and you're wondering whether he has too
  • How he knows the host of the party
  • How you feel about an exciting event
  • How the warm weather has affected the day
  • Whether you've seen him at this place before

3. Start the Conversation With a Question

An observation can start a conversation, but it can also fall flat. That's because an observation doesn't actually ask for an interaction with him; he won't need to give you a long answer. Instead, it's better to walk up to him with a great question based on your shared environment. Here are some ideas:

  • Wow! I completely love the music tonight. Have you heard these guys before?
  • Isn't Sawyer awesome? He always has people laughing in my Econ class. How do you know him?
  • I was worried this party wouldn't happen because of the weather, but it's perfect today! You're not too hot, are you?
  • I come to this cafe every day, and I don't think I've seen you before. Is this your first time here?

4. Be Prepared to Follow Up

It's a good plan to think a couple of conversational moves ahead. That way, you can approach him with confidence and not worry that the conversation will suddenly grind to a halt with an awkward silence. Think of a couple more details related to your main topic, so you have some more to discuss. If things are going well, you can even throw in a getting-to-know-you question.

man and woman flirting

How to Start a Conversation With a Guy Online

It's a little different starting a conversation with a guy on Instagram, Snapchat, or other online platforms. Here, your environment doesn't offer as much variety for conversation, but that's okay. Because the environment is very specific and shared, you actually have plenty to talk about. The key is to make the conversation about him. Here's how to do it.

1. Choose Something He Has Shared

If you're talking to a guy online, you can see what he's sharing on his social media. You can use this as a springboard for conversation. Take some time to look through his Instagram feed or Facebook profile. Look for things that can spark a conversation. This will be specific to his personality and interests, but here are some possible examples:

  • A photo of his pet
  • A post about a restaurant he enjoyed
  • A cause that's important to him

2. Decide What You Want to Ask

Just like when you're talking in person, knowing how to start talking to a guy on Instagram or another social media platform involves asking a question that will take a little time to answer. A simple comment isn't enough to start a full conversation, and a question with a quick answer won't work either. Try something like these:

  • Your dog is the cutest! How did you find him to adopt?
  • I saw you ate at Pizza Luce. I've been meaning to go there. Do you think it's worth a visit?
  • I loved your post about veganism! What made you decide to become a vegan?

3. Be Ready to Continue the Conversation

Before you send that direct message or chat, come up with a few more things to talk about with him. You'll need to keep the conversation going, and there are lots of ways to do that. One is to offer him a great compliment. Stick to something he's done or is doing, rather than a physical attribute. Another is to come up with a few more follow-up questions about your main topic. You can also add an icebreaker joke if you want to keep things light. Either way, you'll have time to think, since the conversation exists online.

How to Start a Conversation With a Guy You Like Over Text

If you have his number and are wondering what you should text a guy first, there are some strategies to help. Try these ideas:

  • Brush up on conversation starters for texts. Because texting is a little different than online and in person interactions, it has its own rules. Whether you want to be flirty or serious, a great conversation starter is important.
  • After that initial text, you'll need to keep the text conversation going. Try some ice breakers and get-to-know-you questions.
  • Finally, make sure you make it real. Starting a conversation over text is one thing, but actually learning something real about the guy is another. Take some time to learn how to get to know someone better over text.

Put Him at Ease

With some guys, starting a conversation is simple. If you're dealing with a guy who is an extrovert or is super social, he'll handle some of the work of keeping things going. However, not all guys find this easy. It's a good idea to learn how to talk to a quiet guy too, since some guys are shy and may struggle with the conversation. Either way, if you can open with a good conversation starter and put him at ease, he'll be attracted to your confidence.

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How to Start a Conversation With a Guy Confidently