How To Start A Conversation With A Guy: 25 Simple Ways To Do

How to start a conversation with a guy? This is a question most of the girls grapple with. When it comes to their family, friends, co-workers, they might be pros at starting conversations. But when it comes to a guy they’re interested in, most of them are tongue-tied. If you want to talk with someone you are interested in, you must make sure to have an engaging and enjoyable conversation. It should be enough to spark chemistry and a possible start to a beautiful relationship. Since starting a conversation can be a task, read on to know about some best conversation starters with a guy, for both in-person and over text.

In This Article

How to Start a Conversation With A Guy?

Conversations, by nature, flow both ways and are typically a two-way street between two or more people. However, when you’re just starting a relationship, you’re likely to have early conversations via text. While you both are equally invested or responsible for keeping the conversation entertaining and flowing, you must understand how to start a conversation with a guy over text. We’ve compiled a list of the best ways to keep him engaged and invested in the conversation while making it appear natural and relaxed.

1. Open with an inside joke

After introducing oneself, sharing an inside joke could be a great way to initiate a conversation. An inside joke is something that only two people or a small group share, so you’re already indicating something intimate and personal to the two of you.

Teasing each other about a celebrity crush or good-natured teasing about an embarrassing incident are two good examples. As long as it’s all in good fun and no feelings are hurt, this is a great way to start a conversation because very few other people (if any) can talk about the same thing.

2. Lead with open-ended questions

Many conversations die before they can even begin, especially if they start with bland phrases like, “sup?” “Hi” or “what are you up to?”. Do not make small talk, as there are very few responses to these questions that can actively engage the other person or entice them to continue the conversation. It’s a good idea to start the conversation with a question. You can engage him by asking, “how did that presentation to your boss go?” or “what did you do over Thanksgiving break with your family?”. At the very least, it shows a primary interest in what the other person is up to and a willingness to listen. Keep conversations interesting by making them fun and interactive to capture the guy’s attention.

3. Follow up on something you spoke about earlier

An excellent way to start a discussion with someone is to continue from where you left off in your previous chat! Of course, we don’t mean resurrecting some long-forgotten conversation or topic. But you can make a lot of progress if you strike up a conversation with something like “Oh, wasn’t today your interview with that new company? Best wishes! I’m confident you’ll do well” or “I decided to check out that band you mentioned the other day, they’re pretty good!”. This will ensure continuity and demonstrate that you are a good listener with a good memory.

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4. Talk about a shared interest

Talking about a shared interest has many advantages because it shifts the focus away from you and onto the topic at hand. This can be helpful because it makes the entire conversation more casual and puts less pressure on you. Discuss a show you both enjoy watching or a sport that you both follow. Texts like “Did you catch the XYZ game last night? It was so close!” or “I missed yesterday’s episode of ABC show, was it good? No spoilers!” will set the mood for a great conversation.

5. Share an old memory

Start a conversation with a guy by sharing an old memory

Image: Shutterstock

If you’ve known each other in some capacity for a while, chances are you’ll have pictures, memories, and other records of your time together, which provides an excellent starting point for a conversation. You can always say, “I can’t believe we started working together two years ago today!” or “I’m so excited for the final movie in this trilogy, I can’t believe we saw the first two years ago.” Nostalgia is a strong emotion and can serve as a good starting point for a conversation.

protip_icon Point to consider
Just go with the flow. The more you overthink, the more you are likely to get stuck on your words or say something stupid. Even if you start with a “Hello, how are you?” it sets a platform for a meaningful conversation.

6. Ask for help with something

Men have a “hero complex” or a “savior complex,” making them help women instinctively. It has a solid biological basis and can be easily triggered. You don’t have to be in a life or death situation to ask him how to fix an appliance or figure out a feature on your computer or anything else he might be good at. It will not only be a great, innocent start to a conversation, but it will also make him feel needed and helpful, which will set the tone for the conversation.

7. Sprinkle in pop culture references

Maybe you’re both die-hard comic fans or enjoy the same TV show or director. In any case, pop culture is a great topic to bond over because it takes the focus and pressure off yourself as the subject of the conversation. So go ahead and start a conversation with a movie quote or a music lyric that you both know and love. It can be a great opening line as long as you don’t overdo it or make it the sole basis of the entire conversation.

8. Ask them for advice on specifics

This isn’t just something that works well while talking to men. People, generally, are social beings who enjoy sharing and learning from each other’s experiences. So it’s perfectly normal to approach a guy and seek his advice on a subject which he may be more knowledgeable about than you. You could always say something like, “I’ve never been to France, you visited last summer, right? What are some must-see places?”. This demonstrates to them that you not only value their opinion but that you are also a good conversationalist.

9. Invite opinions instead of making statements

Invite opinions, how to start a conversation with a guy

Image: Shutterstock

When you make a statement like “I’m going on a diet,” it limits the scope for further conversation. Instead, try to invite their opinions on matters and engage in a meaningful discussion and interesting exchange of words. Phrase it more like “I feel like I need to cut down on junk food, what do you think?” making them feel like they’re involved in the decision-making instead of just being informed of something you’ve decided to do.

10. Give them an update on a mutual friend

Many conversations between people who have mutual friends are often about them. So it’s uncommon to bring up a mutual friend or a development in their lives, such as getting engaged, moving to a different city, or changing jobs. Talking about these things isn’t even gossip because these are significant events in their lives that they would expect people to talk about, especially life milestones like getting engaged. You can always say something like, “Did you hear our good friend XYZ is moving to Canada?” or “I can’t believe ABC is having their first kid!”. It emphasizes the fact that your friendship extends beyond the two of you.

protip_icon Do remember
Do not use a controversial topic (like politics or religion) to start a conversation. If you have contrasting opinions, it might lead to future bitterness and resentment.

How To Start A Conversation With A Guy Over Text?

Texting is a natural evolution of communication. While texting will never truly capture the magic of speaking in person or even speaking in real-time over a video or phone call, there’s a different dynamic to texting.

1. Lead with confidence

If you are wondering how to start a conversation with a boy on text, remember that being the first to reach out may be intimidating at first, but it also demonstrates that you are bold and confident in your approach. Don’t be afraid to reach out to him out of the blue and initiate a conversation. Allow them time to respond and revert when available, and then casually continue the conversation with jokes and other conversation starters. A good example is a joke question that he must guess or answer. This will go a long way toward stimulating the conversation.

2. Use an emoji or GIF

An emoji or popular .gif file can sometimes very accurately capture an entire vibe. Something that correlates with “ugh Mondays” or “I’m too hungover to work” or “my face when I realize the long weekend is coming up” can be more than just a conversation starter. It will not only put a smile on the guy’s face, but it will also start your conversation on a relatable note.

3. Don’t overthink the timing

There are objectively good and bad times to call someone, but a text is somewhat unaffected by social conventions. So if you’re thinking of a guy, send him a casual text message without overthinking it. It could be at midnight, or 6 am, and there’s nothing wrong with sending it at either time. He’ll get back to you when he’s available, or if he’s up late (or early), in which case you can have a fun insomniac conversation with him! The joy about texting is that you do not need to wait for an immediate response, and this also opens up for free conversation where someone can respond when they are free.

4. Be authentic

Texting may appear to put a filter between you and the other person that an in-person conversation does not, but it’s still the two of you talking. Ensure you always text the way you speak or aren’t completely different when you text him. Although it may be tempting to overthink and edit our texts before sending them to present the “best versions” of ourselves, people will value authenticity and honesty in all social interactions.

5. Share a picture

Share your picture to start a conversation with a guy

Image: IStock

Everyone has heard the phrase “a picture is worth a thousand words”, but one of you, or just you, can be a great conversation starter. It could be a wacky hairstyle, a goofy shirt, or a kitchen disaster, but it’s sure to spark a funny conversation. People are also more inclined towards visual mediums than text, so their chances of noticing and responding to those are higher.

protip_icon Point to consider
If you ask too many personal questions, it might make the person at the other end uncomfortable. So keep the questions and conversations lighthearted.

6. Ask if you can vent

This may appear to be counterintuitive, but it’s far from it. We all have our limits as humans, and we all snap at times. Before we reach that tipping point, it’s a good idea to have someone to talk to, even if it’s only through text messages. Just let them know, “Just had a terrible day at work, need someone to talk to, do you have a sec?”. If they are available and willing, they will gladly listen to you out of curiosity, if not for the sake of your friendship. Another advantage is that it demonstrates that you are available to him if he ever needs to vent.

7. Ask for recommendations

It’s never too late to try a new show or movie or read a new book or new musician. You can always start a conversation by asking a guy for advice for any of these. You could even phrase in a way that demonstrates your appreciation for his taste and recommendations, making him happy. Something as simple as “you have pretty good taste in music, what are some good 80s songs I could check out?” can be a huge confidence booster and a great start to the conversation.

8. Share some memes with them

If jokes aren’t your thing, you could always send them a meme! A meme is essentially a joke but in a recognizable and relatable pictorial format. So, regardless of the time of day or the subject, you could always send a funny meme you found online to a guy friend. Odds are you might get variations of that meme or similar memes from them and establish a meme-sharing or joking relationship with them. Meme sharing is an upcoming way of communication and building a bond. You could make a relatable meme on an inside joke, and this could create an intimate bond.

protip_icon Quick tip
Share memes that suit your present mood. This will make the conversation fun and easy and foster the connection.

9. Give them an update on your pet(s)

This is a great way to start a conversation if you and your friend are pet owners or even just pet lovers! To begin the conversation on a lovely note, show them a cute picture of your cat napping on the sofa or a picture of you coming across a litter of newborn puppies. The best part is that you’re bonding over something wholesome and joyful to both parties, so there’s little pressure to “keep the conversation going”. If both have pets, you can always send each other pictures of your pets doing silly things.

10. Update them on your workouts!

Update them on your workouts

Image: IStock

With the rise of wearables and the ability of your smartphone to track your physical activity, it’s easier than ever to see how many calories you’ve burnt, steps you’ve taken, and so on. This also makes it simple to communicate your fitness goals and progress to your friends. Apps such as Strava and Apple Health have the “Share” feature that allows you to share your overall health and exercise levels. By sharing your healthy lifestyle with your guy, you’re creating memories and associating healthy living with fun times. There are numerous ways for you and your guy to encourage each other to get healthier, ranging from competing against each other to using fitness as a shared goal. If you have a competitive streak, you even challenge them to beat your score.

11. Reference their social media or dating profiles

If you met this person through social media or a dating site, it’s a good idea to include a picture or their bio from that site. You could always say something like, “Hey, you mentioned you like to play guitar. Do you think you could teach me some basics?”. It will not only reinforce that you are paying attention to their profiles, but you will also want to engage with the aspects of their personality they have uploaded online.

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12. Be mindful of the timing

You should have a good idea of the guy’s schedule if you’re close to him, and you should text him accordingly. Trying to start a text conversation while he’s driving to work or at the gym will fail. Of course, he may return to the messages later, but the momentum has been lost by then. Ideally, you should text him when he is free and available to respond, keeping the conversation active and engaging for both of you in the present. So, while texting him, keep an eye on the clock and weekend/weekday schedules.

13. Keep it light and playful

While we can discuss serious issues via text, no one wants to debate the Middle East conflict or discuss their taxes. If you want to socialize with them, it is best to keep the conversation light. When texting a guy you like, keep the topics playful and light, so he feels like texting you about those things to escape from stressful factors in his life, such as work or finances. Try to keep the conversation light and fun and avoid serious topics unless he wants to discuss or vent to you about it. Make the conversation interesting and happy, so he always wants to talk to you when he’s having a stressful day.

14. Be clear in the tone of your messages

Texting is convenient in many ways, but it also has drawbacks. Perhaps, the most obvious is how difficult it is to convey tone via text message. If you haven’t gotten close to a particular guy yet, you should re-read your messages before sending them to ensure that the intended meaning and tone are conveyed. People can often sound sarcastic, irritated, or even upset over text, leading to miscommunication and even conflict. Ensure your intended message is clear and vocal, and make liberal use of emojis and memes to ensure there is no room for confusion.

15. Avoid asking questions if possible

Avoid asking questions if possible

Image: IStock

When we’re asked a question, we usually respond by answering it. However, when we open our phones and look at our texts and see a slew of questions from various people, our brains classify them as “work” because we have to respond to them. Make sure that your text interactions do not appear to him to be an effort. This is not to say that you shouldn’t ask questions or seek advice, but try not to wake him up to a barrage of questions in his inbox that he feels obliged or burdened to answer.

Frequently Asked Questions

1. How can I start a conversation with a guy I don’t know very well?

You could start by introducing yourself and asking his name, then follow up with a casual question, comment or ask an opinion to get the conversation going.

2. How can I start a conversation with a guy without seeming too nervous or shy?

Prepare a few conversations ahead of time. Act confident even if you are not, and take deep breaths to calm your nerves before approaching them.

3. How can I use body language to start a conversation with a guy and make it more engaging?

Make eye contact and smile, lean in slightly to show that you’re interested, and use an open and relaxed body posture to show that you’re approachable and friendly.

4. What are some tips for starting a conversation with a guy at a social event or party?

When starting a conversation with someone at a social event or party, it can be helpful to find common ground or a shared interest to build on. Commenting or stating an observation from the event can be a great conversation opener. Be open and friendly, and focus on favorites. Show genuine interest throughout the conversation.

5. How can I start a conversation with a guy I see regularly but haven’t spoken to before?

Start by introducing yourselves. Stay calm and let the conversation flow naturally. Ask about their day or week, comment on something in your shared surroundings, or find a shared interest to talk about.

6. How can I use humor to break the ice and start a conversation with a guy?

Humor can be a great way to break the ice and make a conversation more engaging and memorable. Look for opportunities to make a joke or share a funny observation. Ensure that the joke is lighthearted and not demeaning.

Many girls often wonder how to start a conversation with a guy and take it forward naturally. If you are among them, you may know how pressurizing it can be to make the conversation enjoyable and productive. The trick is to stay relaxed and let the conversation flow. Talk about a shared interest, ask open-ended questions, or share an old memory with them. Let your conversation flow naturally instead of making it feel like a chore. If you’re texting the guy, the rules stay the same. Be confident and original in your texts. You can make your conversations silly and funny too. Being yourself will help make your text conversations enjoyable and provide them with a pleasant break from their daily routine. Having regular conversations will also help create good chemistry.

Infographic: How To Start A Conversation With A Guy?

Conversations present you with a chance to get to know each other better. But starting that conversation might be a challenging task for some. We are sure that with the help of this post, you will be able to find the right way to start a conversation with a guy. In addition, we have also prepared this infographic to help you with a few more tips regarding the same.

tips on starting a conversation with a guy (infographic)

Illustration: Momjunction Design Team

Get high-quality PDF version by clicking below.

Download Infographic in PDF version Download Infographic
Download Infographic in PDF version

Key Pointers

  • An effective way to keep the conversation flowing with the guy is to ask open-ended questions.
  • If you both have a shared interest or an old memory, it can be a great conversation starter.
  • Be it through a text or in person, remain confident and authentic.
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