How to Start a Conversation with a Guy

Co-authored by Lynda Jean

Last Updated: October 25, 2022 References Approved

Starting a conversation with a guy can be a nerve-wracking process, especially when you think he's cute. But if you can pluck up enough courage to just go for it, the results can be oh-so-worth it. Here are some simple, easy-to-follow tips and tricks for striking up a meaningful conversation with a guy. Think about it this way, guys are people who do think of themself as friends, and believe it or not, boys get nervous when talking to girls sometimes as well.

Things You Should Know

Use the circumstances around you as an icebreaker. For example, you could comment on the weather or ask him if you can borrow a pen.
To keep the conversation flowing, ask him open-ended questions until you discover a common interest that you can both easily chat about.
Remember to make eye contact and smile during the conversation so you make a great impression.

Part 1

Part 1 of 3:

Getting Him Talking

1
Introduce yourself. The most straightforward way to get a guy talking is to walk right up to him and introduce yourself. It doesn't matter if he's the new guy at work, the cute boy you've noticed around the school corridors, or the handsome stranger at the coffee shop - put your shoulders back, plant a smile on your face and approach him confidently. Say hi, tell him your name and ask for his - if you're lucky he'll take it from there!^{[1]
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- Once you find out the guy's name, use it frequently in the conversation. People like to hear their own name - it makes the conversation more personal and creates a sense of intimacy between you. Just be careful not to overdo it!^{[2]
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  Expert Source
  
  Lynda Jean
  Certified Image Consultant
  Expert Interview. 17 November 2020.}
- Say something like "Hi, I've noticed you around here and I just thought I'd come over and introduce myself. My name's Kate, what's yours?" Simple!
2
Use the circumstances around you. One of the easiest ways to start a conversation is to take advantage of your surrounding circumstances to get him talking. It could be literally anything, from the weather, to the traffic, to the results of a sports game. You can either make the comment to him directly or to yourself, hoping he sees it as an opportunity and responds.^{[3]
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Lynda Jean
Certified Image Consultant
Expert Interview. 17 November 2020.}
- Commenting on the weather may seem like a mundane conversation starter, but it works nevertheless. Try saying something like "Beautiful day, huh? Don't you just love the sunshine?" When starting a conversation with someone you don't know, the point is to break the ice and open a line of communication first. Once you've done that you can move on to more interesting topics.
- If you're sitting next to a cute guy on the train or an airplane, try sighing and muttering to yourself about the delay or bumpiness of the ride. If he's interested, he'll take this as his cue to respond in sympathetic agreement. Once you have his attention, you can take it from there!
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3
Ask him for help. Men love to help women. They're biologically wired that way. So engaging the damsel in distress routine from time to time might just help to get the conversation going. Appeal to his manly muscle and strength - it will give him a confidence boost and make him feel more comfortable around you, allowing conversation to flow more freely.^{[5]
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- If you're struggling with a heavy stack of files or a bulky box, ask if he can help to lighten the load. If you just can't seem to open the coffee jar or unscrew the cap of your water bottle, see if he'll oblige.
- Make sure to smile and thank him sweetly after he helps you - everyone likes a little appreciation when they do a good deed. And he'll be ready to jump at the opportunity to help next time round.
- This step also comes with a warning: don't overdo it. You want a guy's respect as well as his attention, so don't play the damsel in distress too often or you'll come across as helpless.
4
Compliment him.^{[6]
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Research source} Guys like compliments just as much as girls do, so paying your guy an enthusiastic, genuine compliment will definitely get you in the good books and optimize his interest in the conversation. Paying him a compliment is a great conversation starter as you can be as intimate or as casual as you like, depending on how confident you're feeling.
- If you're feeling forward, compliment him on his amazing eyes, his killer six-pack or his George Clooney smile. This will let him know that you find him physically attractive, which all guys love to hear.
- If you're aiming to be a little less obvious, compliment him on his snappy suit, his funky band tee or his great-smelling cologne - letting him know that you think he has great taste.
- Compliment him on his performance at work or on the sports field, if you happen to be present at the time. Tell him he did a great job on the presentation or that he played really well. He'll know that you were paying particular attention to him.
- Alternatively, you can compliment him on something a little less personal. If you run into him walking his dog, compliment the dog instead (earning you major guy points). Or tell him that you approve of his choice of sandwich at lunch. Anything that grabs your attention and gets him talking.
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Ask a question.^{[7]
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Research source} Questions are great conversation starters, especially if you're feeling a little awkward, as they provide you with an excuse to talk to the guy under the pretense of seeking out information.^{[8]
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Expert Source

Lynda Jean
Certified Image Consultant
Expert Interview. 17 November 2020.} The questions themselves can be as short and simple as you like. Just try to avoid questions that can be answered with a short "yes" or "no" as this can lead to awkwardness, causing the conversation to fizzle away.
- Phrase questions in such a way that he will be forced to think about the answer, or at least provide more than a monosyllabic response. Men can be a little dull at times, so try to help them along a little. He'll soon realize that you're more interested in him than in finding out what time it is.
- Try asking him if he has a pen you could borrow or if he watched the basketball game last night. At this point it's just about grabbing his attention and getting the conversation going, so don't worry too much about the topic.

Part 2

Part 2 of 3:

Keeping Him Talking

1
Find a shared interest. Finding a shared interest is conversational gold. When you find a topic that both of you enjoy talking about, the conversation will flow much more easily. Even if it's something you're not particularly knowledgeable about, demonstrate your interest by asking him plenty of questions and allow him to do the talking.
- For example, if you discover that you both like to watch football, ask him about his favorite team, who he thinks their best players are and whether they'll make it to the playoffs this year. Once you get him going there'll be no stopping him, and he'll probably think you're a pretty cool girl for being interested.
- Pick up on hints about his interests from his clothing, desk or accessories. If he's wearing a band tee - bingo! He likes music. If he has a surfing picture set as his desktop background, that's a pretty good indication he likes to ride the waves. Picking up on small details can help you to choose the right topic to get him going.
2
Ask open-ended questions. To really get the conversation going and to find out about your guy's interests and personality, it's important to ask open-ended questions. Avoid questions with one-word answers or rote questions that he'll automatically answer without thinking.
- For example, avoid starting a conversation with "how are you?" which he'll probably answer by reflex with a "fine" or a "good". Instead try asking him "what did you do this weekend?" or "what do you think of the new boss?" which will force him to think about his answer and actually string a sentence together.
- Alternatively, you can try asking him an "either-or" question, to initiate a playful debate. Ask him whether he prefers "The Simpsons" or "Family Guy", rock or hip-hop, burgers or hot dogs. Whatever he answers, gently tease him about it and soon you'll both be laughing.
3
Listen more than you talk. Conversational etiquette dictates that you should always listen more than you talk.^{[9]
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Lynda Jean
Certified Image Consultant
Expert Interview. 17 November 2020.} That's why you have two ears and only one mouth, right? So once you've got the ball rolling, take a back seat during the conversation and really listen to what he's got to say. Let him take charge of the conversation for a while - in case you've never noticed, guys tend to like the sound of their own voice.
- Even when you're not talking, try to stay engaged in the conversation. Acknowledge things he says with a smile, nod or other appropriate facial expression or gesture.
- Being a good listener during your conversation does two things: it allows you to make a good impression, letting the guy know that you're thoughtful and easy to talk to, while also giving you the chance to see whether you actually think this guy is worth your time.
- From the things the guy says, you'll get a pretty good idea of his personality and you can think about whether you want to take the next step. This is important because - let's face it - if you don't find him interesting now, you won't find him any more interesting on a date.
4
Pose an interesting question. On the other hand, if you've got nothing to say for yourself, he may not find you very interesting. Elevate your conversation beyond everyday chitchat by posing an interesting or thought-provoking question that will make him think and ensure that you make an impression. Give him something to ponder and you'll be in his head long after the conversation has ended.^{[11]
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- For example, ask him fun yet interesting questions like "If you could visit anywhere in the world, where would it be?" or "If your house were on fire, what three things would you save?" or "If you were a fictional character, who would you be?" These questions will hopefully make him smile and give you a little insight into his personality.
- Or you can get a little more serious and personal and ask him questions like "what is your biggest regret in life?" or "where do you see yourself in ten years?"
- Just to be clear, these are not the kind of questions that you ask to open a conversation or that you bring up completely out of the blue. If you do, he'll probably think you're just a teeny bit crazy. These questions are best reserved for when the initial awkwardness has passed, maybe after a couple of drinks.
5
Bring up pop culture. Pop culture is the old reliable when it comes to conversational material. Everyone, no matter what their interests, will have something to say about movies, music, television shows, books or the latest crazy celebrity baby names. Once you've gotten a sense of what his interests are, you can ask him whether he's seen a particular movie, read a particular book, or heard a popular band's new record.
- Also try asking for the guy's opinion or recommendation when it comes to an aspect of pop culture he considers himself an expert on. Guys love to show off their vast knowledge, especially to a rapt audience.
- For example, if he loves Woody Allen movies but you've never seen any, ask him which is the best one to start with. Feeling confident? Maybe you could suggest watching it together.
- Or if you can find something random that you're just as knowledgeable about as he is, you're in luck. Impress him with your love of obscure 70's punk-rock bands or your readership of Franco-Belgian comic books. He might just think you're The One.
6
End on a high note. The final step in successfully conversing with a guy is to know when to gracefully bow out. You should always leave him wanting more, not wishing you'd take the hint and leave. After a particularly successful joke or story, you should try to make your exit. Tell him that you need to get back to work or should be getting home. Hopefully he'll be disappointed you're leaving and will look forward to the next time you get a chance to talk.
- If you feel that things really went well and you like this guy even more now, put yourself out there and suggest that the two of you go out for coffee or drinks after work sometime. If you feel too awkward to say it out loud, do like the girls in the movies and slip him your number on a scrap of paper.
- Right before you leave, you should look the guy straight in the eyes, flash him a smile and say "I really enjoyed talking to you, *insert guy's name here*" It's personal, it's flirtatious and it's so much more memorable than "see you later".

Part 3

Part 3 of 3:

Sending the Right Signals

1
Smile and laugh. Guys are more attracted to happy, laughing, smiling girls than scowling, duck-faced divas. Fact. Smiling makes you seem friendly and approachable before you even open your mouth to speak.^{[12]
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Research source} He'll instantly feel more comfortable around you and be more willing to open up. Laughing at his jokes will boost his ego and make him feel good, while also making you look more attractive. Win-win.
2
Make eye contact. Eye contact is one of the most vital aspects of successful conversations.^{[13]
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Expert Source

Lynda Jean
Certified Image Consultant
Expert Interview. 17 November 2020.} Think about it. If you are constantly averting your eyes or looking away you'll either look awkward and uncomfortable or as if you're not interested in being there at all. Plenty of eye contact projects confidence and indicates interests, which is exactly what you're trying to achieve. Be careful not to stare though, that's just plain creepy.
3
Be subtle. Ok, so you want this guy to know you're interested, but you don't need to wave it in front of his face. You can smile at him, make eye contact, laugh at his jokes and ask him questions, but don't do it too often or hang on his every word like an over-eager puppy. Try to retain a little bit of mystery and make him work a little for your attention. Guys like the chase, remember?^{[15]
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Look your best.^{[16]
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Research source} Attraction isn't always physical, nor should it be. You want a guy who's attracted to your intelligence, your sparkling wit, your sweet nature and maybe your ability to chug a pint of beer in under 7 seconds. But when trying to get a guy's attention, it doesn't hurt to look your best. This doesn't mean high heels and a full face of make-up. Rather it involves things such as dressing to suit your figure, always having freshly-washed, sweet-smelling hair or wearing make-up that draws attention to your best features, such as your full lips or beautiful eyes.
5
Don't overwhelm him. Asking questions and getting to know this guy better is all perfectly fine, but try not to scare him off either. Don't ask him questions that you wouldn't feel comfortable answering yourself. Also, try to keep the questions breezy - you don't want him to feel like you're scrutinizing his answers, as if he were interviewing for a job or being cross-examined on the witness stand. Play nice.
6
Make physical contact.^{[17]
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Research source} A subtle brush against his shoulder or a hand lightly placed on his arm mid-conversation can give a guy chills and let him know, without having to say a word, that you're interested. You shouldn't overdo it, but once or twice over the course of a conversation will achieve just the desired effect.
7
Ask him out. This is what it's all been leading up to, right? If you've spoken to your guy, decided you like him, and you're pretty sure he likes you back, why not bite the bullet and ask him out? It doesn't need to be a big, romantic gesture or anything so formal as dinner. Try asking him if he'd like to a grab a coffee (or something stronger) after work on Friday.^{[18]
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Research source} This will give you a chance to spend some more time together without being in an overtly date-like situation. Just think of it as an extra opportunity to work on your conversation skills. Not so scary at all!

Warnings

Don't ask him if he likes being single or if he has ever been in love. He will probably think of you as pushy, or as if you're moving too fast in your relationship and it might scare him off!

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If you put yourself out there and ask a guy out, there's always a chance he'll say no. Don't feel too hurt or rejected if this happens, just pick yourself up and keep smiling. Someone better may come along.

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