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How to start a conversation with a guy: 9 tips

Nowadays, anyone can go on Instagram and leave a couple of likes or react to a story to show some interest. But interacting and starting a conversation for the first time, either in person or online, is a new challenge. Knowing how to start a conversation with a guy without falling into the typical cliché topics or awkward silences, avoiding coming across as basic or too gossipy, takes a bit of preparation.

How to start a conversation with a guy: 8 tips

You don’t have to do a masterclass or learn anything by heart, but there are some aces you can hide up your sleeve to break the ice and make the conversation flow as naturally and smoothly as possible.

1. Be self-confident

Yes, being shy can make a cute impression at first. But being too shy will highlight your negatives more than positives if you’re interested in having a conversation.

On the other hand, if you’re confident (or introduce yourself as such), even if you’re having the banalest conversation in the world, it will make you seem much more attractive. Any mistakes you might make will appear much smaller and even funnier if you know how to speak with a smile.

Nothing is more captivating than a confident person, even if you have your insecurities deep down.

2. Find common ground

It’s effortless to find something in common. Look at his social media accounts or even what his looks tell you. If you see that each photo has a different location, you can talk about your trips and ask which was his favorite and why. If he’s wearing a band t-shirt, you can bring up the music, or if he has tattoos, ask if they have any meaning or thinks tattoos can be helpful simply for aesthetics, etc.

Remember that it’s about having things in common, but you don’t necessarily have to agree on everything. Above all, be honest and act naturally. Sometimes it’s good to complement each other and not be similar in everything.

how to start a conversation with a guy - find common ground

3. Be interested in his interests.

Take the opportunity to ask about that topic that you think has more juice. For example, if you’ve encountered a musician or a reader, you can ask about his passions. Even if he is a timid guy, we all like to talk in detail about what we are passionate about.

In addition, there are many questions you can ask about it, such as when he discovered it was his passion, how he feels about it, or if he sees a future for it.

4. Avoid “yes”/”no” questions

Very important: It is not about learning everything about the other person in a first conversation, nor on a first date. It is essential to get to know each other little by little. This process will inevitably happen as you talk. There is no rush.

What is essential is to create a connection and feel comfortable talking to ensure that you both want a second date or conversation. Therefore, think of questions that are not too personal or intense but give you a little more talk, and avoid the “yes or no” questions.

5. Avoid interrogations

Don’t try to ask questions all the time, either. You are getting to know a person, not filling out a form.

It’s okay to ask questions to discover certain things, but you’re not collecting information as if it were a thesis. Make general comments that keep the conversation flowing without asking question after question because the guy is likely to get overwhelmed.

6. Be open so that he will open to you.

If you’ve run into a timid person, you may end up in that interrogation-like loop of asking questions. In this case, try to open up first.

Without forcing things, if you open up and tell something personal (but not too emotional, remember it’s the first conversation), you’ll create a safe space and make the guy feel more comfortable expressing himself.

how to start a conversation with a guy - be open

7. Avoid complicated topics

In a first conversation, it’s all about connecting and having a good time talking.

First impressions are not the most important thing, but they are the element that will open the door to future conversations.

Therefore, avoid starting conversations with controversial, complicated, or uncomfortable topics. Avoid essential “what’s your favorite color” questions, but don’t get too philosophical or politically tricky in the first contact.

8. Think of a different question

If the conversation is flowing, at some point, it might not hurt to ask a more interesting question that allows you to change the tone slightly. This way, you can show a little of your original side.

Depending on where the conversation has gone and how much the guy has opened up to you, you can ask the question, “Where do you see yourself in ten years?”, “Where would you travel right now if you could?” or “What is your biggest regret?”.

Avoid asking a tricky or intense question if you haven’t gone too deep into the conversation.

9. Key: The farewell

If you liked it, let him know. The good idea is to say something you would like to do in the next few days in the city, which he might also be interested in. If he replies that he wants to do it too, remember to tell him to meet you again to carry out that plan. It’s a piece of cake.

How to start a conversation with a guy – The bottom line

First contacts can sometimes be complicated, and it is good to prepare yourself mentally to feel more confident. However, remember that the idea is to have a good time without forcing things.

These tricks can help you get out of awkward silences and feel more at ease with a “backup plan.” But the most important thing to remember is that you can’t force connections and that there won’t always be a second conversation. The important thing is that you enjoy it.