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

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

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Every day, we have conversations with various people, whether friends, coworkers, or family. When you’re about to talk to a guy you’re interested in, the stakes are slightly higher. You must ensure that your conversations are enjoyable and engaging enough to foster chemistry and possibly even the start of a relationship. However, starting the conversation is the most challenging part. Here are some of the best ways to start a conversation with a guy, both in person and over text, that you can use the next time you want to start a conversation with someone special.

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

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?”. 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.

3. Follow up on something you spoke about earlier

An excellent way to start a conversation with someone is to carry on from where you left off! Of course, we don’t mean resurrecting some long-forgotten conversation or topic. But you can make a lot of progress if you start your 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.

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

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.

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

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. 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.

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

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!

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

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.

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.

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!

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.

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. 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 stay away from serious topics unless he wants to discuss or vent to you about it.

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

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.

Starting a conversation can be stressful because you have to keep it going and feel pressured to ensure the conversation is enjoyable and productive. Sometimes all you need to do is take a step back and relax as you begin a conversation and allow it to flow naturally. This way, it won’t feel like a chore or something to “perform” well at, but rather like a natural, organic flow of conversation between two people.

When it comes to texting a guy, the same rules apply. You can text almost any time and from any location and be utterly casual about it. The response may come hours or even days later, and it can be a conversation about something silly or nothing at all while still being a fun interaction between two people.

By keeping some of these simple rules in mind, you can ensure that your text conversations with guys are always a welcome break from their routine and lead to further good chemistry between the two of you.