Conversation skills don’t come naturally to everyone, but it can be especially hard to start and keep a conversation going with guys. There are a lot of stereotypes about the supposed differences between male and female communication styles, but many aren’t scientifically proven. While some guys may be more closed off, less social, or not as into long conversations as girls, each guy is an individual. This makes it hard to know how to talk to a guy, especially when you’re still in the “get to know you” phase.
If you’re talking to a guy you like or have a crush on, conversations can be even harder. It’s common to get stuck overthinking your conversations or worrying about what to text a guy you like. Preparing some topics and examples of things to say can help you to enjoy these conversations instead of stressing out about them.
This article will give you ideas and examples of how to start a conversation with a guy online, through texting, or in person, and how to keep the conversation alive.
- How to start conversations with guys online
- How to keep a conversation going with a guy
- Common questions
How to start conversations with guys online or offline
Today, about one in three adults have used a dating app like Bumble, Grindr, Tinder, or Hinge. These apps have definitely made it easy to meet and match with guys, but they haven’t made dating any less stressful. In fact, two-thirds of adults on the dating scene aren’t satisfied with their experiences, and feeling uncomfortable approaching people is one of the main problems.[1]
For straight women, there are also concerns about risk and safety, and 57% of women experienced some kind of harassment.[1] For this reason, most women on dating apps want to have some 1:1 interactions before agreeing to meet up with a guy they just met online.[2]
These early interactions are important because they’re used to determine whether or not there’s chemistry and to screen out people who make them uncomfortable.
In the current world of online dating and “matching” with guys on apps, some conversation starters are better than others. The best ones are designed to help you get the information that helps you figure out whether or not to meet up with someone. Here are some tips for starting conversations with guys you meet online or on apps:[2][3][4]
1. Personalize your approach by mentioning something that stands out
Online example: “I love your picture of you and your pup! What breed is it?”
Offline example: “Your T-shirt is amazing. Where’d you find it?”
2. Find common interests and build off them
Online example: “Hey! It looks like we’re both into movies. Seen anything good lately?”
Offline example: “It looks like you’re a basketball guy. Who’s your favorite team?”
3. Keep it simple by just saying hi and introducing yourself
Online example: “Hey, I’m Kim. I like your profile!”
Offline example: “I don’t think we’ve officially met. I’m Kim.”
4. Talk about your shared experiences
Online example: “I haven’t used this app before, so I’m still figuring out how this all works!”
Offline example: “I’ve been with the company for only a year. What about you?”
5. Give them a compliment to build a bond quickly
Online example: “I love the way you kept it real in your profile. So relatable!”
Offline example: “I’m a fan of guys who are polite, so you just got major bonus points!”
6. Ask about meeting up or talking more 1:1 if you feel comfortable
Online example: “Loved chatting so far. Would you be up to meet up in person?”
Offline example: “Hey, I was thinking we could grab a beer after work one night?”
How to keep a conversation going with a guy
Once you’ve started the conversation with a guy, it can be difficult to know how to keep it going with good topics that are interesting, funny, and engaging. Below are 15 strategies to keep conversations going with a guy. The earlier steps are great for guys you’re trying to get to know, casually date, or become platonic friends with. The later steps are best for guys you have already gotten close with, including a guy you’re dating or trying to get serious with.
1. Check in if it’s been a few days or more
When you’ve been chatting or texting with a guy, make sure to check in after a few days have gone by, especially if you’ve been in regular contact. It can feel awkward to pick the conversation back up if you’ve waited a week or two, and some guys might worry you ghosted them.
If you’ve been MIA or forgot to respond to a text with a guy you like, make sure to fill in the gaps by apologizing and giving a brief explanation for your late response. A simple text like, “Sorry, I thought I replied” or, “Crazy week… just seeing this!” followed by a check-in can help avoid misunderstandings.
2. Ask open-ended questions to get them talking more
Another great way to keep a conversation going with a guy is to ask open-ended questions to get to know them better. Unlike closed questions, open-ended questions are ones that can’t be answered in one word or with a simple “yes,” “no,” “OK,” or “good.”[2][4]
Open questions are great tools to keep a conversation going because they tend to encourage longer, more detailed responses.[3] This means less pressure on you to carry the conversation or come up with new topics. Examples of good questions to ask a guy you like are asking him to tell you more about his job or asking him to describe his hometown.
3. Show interest in things they like
While you might want to seem interesting to impress a guy, showing interest in him is more likely to make a good impression. When you show a sincere interest in things that a guy is talking about, it can help to build trust and closeness with them.[3][4]
Showing interest in the things that matter to him is a great way to show that you’re interested in him. This doesn’t mean you need to pretend to be a huge sports fan or movie buff (if you aren’t interested in them), but it does mean being open to talking about these topics. To do so, you could ask “What are you streaming?” “Who is your favorite team?” or “What’s your all-time favorite sci-fi movie?”
4. Use easy questions to get to know him better
When you are still trying to get to know a guy, it’s a good idea to start off with light and easy topics and questions rather than going straight for the deep, serious, or personal ones.[4] Easy questions are ones that allow him to decide how much or how little to share. Try to avoid sensitive, stressful or controversial topics.
Good questions don’t require a lot of deep thought or brainpower. (A series of complicated questions can feel more like an IQ test than a conversation when you’re on a first date.) Some examples of easy questions to ask a guy you like and want to get to know are:
- “What kinds of things do you like doing in your free time?”
- “What do you like most about your new job?”
- “Do you have any exciting plans or trips coming up?”
5. Pause more to let them lead conversations
If you’re struggling to find things to talk about, it may be because you’re unknowingly dominating the conversation without giving your guy a chance to talk. To avoid talking too much, step back and take longer pauses to allow him time to think and come up with things to say.
Letting him lead takes some pressure off you and gives him a chance to introduce topics he is interested in. By letting him initiate a conversation, you may not have to work as hard to keep a guy interested. If pauses and silences make you uncomfortable, it can be less awkward if you smile, look away, and wait a few seconds before jumping in to say something.
6. Keep things light and positive early on
While there’s a time and place for serious and difficult conversations, these usually are reserved for later stages of a relationship. When you’re still in the early stages of talking to or dating a guy you like, try to keep conversations light, positive, and friendly.[3][4] For example, share good news or something funny that happened at work instead of complaining about your job or coworkers.
Being more positive helps to make a good impression on a guy you just met. When you stay positive, you’re less likely to come across as judgmental, negative, or critical. Just make sure not to overdo it by being too bubbly or happy all the time, which can come off as fake.
7. Sidestep debates and controversial topics
These days, there are lots of current events and relevant topics that can spark heated debates and controversies. It’s wise to try to avoid these kinds of topics when you’re in the ‘get to know you’ phase of a relationship. This is especially true if you’re unsure of his views or opinions on a certain topic, and you might end up disagreeing.
Established relationships need to be strong enough to handle these kinds of conflicts, but they can be deal-breakers early on.[4][5] Some potentially controversial topics to avoid before you get to know a guy are:
- Political views
- Opinions about certain current events
- Religious beliefs
- Prior sexual or romantic relationships
- Money and personal finances
- Family issues and conflicts
8. Look for chances to show empathy
Eventually, there will be an opportunity for you to show your softer side to a guy, which is a good way to begin deepening trust and closeness with him. Don’t try to force this moment, but do stay on the lookout for an opportunity when it presents itself. Showing empathy is one of the best ways to build trust and closeness, even if your goal is to just become friends with a guy.[5]
Some examples of opportunities and ways to respond empathetically are:
- Saying, “That sucks, I’m sorry you’re dealing with that” when he shares something stressful that’s going on at work
- Texting, “No worries, I completely understand!” if he messages you that he needs to cancel or raincheck because something came up
- Responding, “Oh no! Hope you feel better!” if you find out he’s not feeling well or is out sick
9. Allow your interest in them to show
One major mistake that both boys and girls who are dating make is that they try to “play it cool” by acting disinterested when they actually have strong feelings for someone. While this strategy might have worked in middle or high school, open communication is a better approach if your goal is to form a healthy, close, mature relationship.[4][5]
Playing cool or “hard to get” is a dangerous game to play when you have a crush on someone and really want things to work out. This can lead a guy to assume you’re actually not interested in him, causing him to give up, back up, and move on. Avoid these kinds of games by showing sincere interest and letting some of your feelings show. For example, send a text saying you’re looking forward to seeing him before a date or that you had a great time afterward.
10. Use social media and photos to stay connected
These days, it’s pretty normal to meet and talk to people online, using social media or apps like Whatsapp. While texting and messaging aren’t always the best way to form deep, authentic connections, they can be used to share your experiences with someone and let them know you’re thinking of them.
To stay connected to a long-distance boyfriend or a guy you like or just started dating, try:
- Sending a Snapchat video or Instagram photo of where you are or what you’re doing to make him feel included in your daily life
- Let him know you’re thinking of him by sending a personalized message or a text saying you miss him or wish he was there
- Use social media to give a shoutout to your boyfriend by tagging him in an old picture of you two or posting a picture of something sweet he gave you or did for you
11. Find things you have in common
It’s natural to be attracted to people who are similar to us, so finding things in common with someone is an important step in relationship building.[4][5] Avoid being too quick to judge a guy based on how he looks or acts when you first meet him. One of the best ways to find common ground with a guy is to open up and share things about yourself, including:
- Hobbies, random interests, or fun facts
- Music, movies, or shows you like
- Activities and events you enjoy
- Professional interests or goals
- Places you’ve traveled or want to travel to
You might also like some ideas from this article on things to do as a couple.
13. Remember important dates and details
Remembering important dates and details a guy shares about things going on in his life is a great way to demonstrate that you care and are paying attention. This may involve becoming a better listener so that you can focus more on listening and retaining what he says to you rather than getting too wrapped up in what you say to him.
Here are some examples of important details and dates and ways to use these to spark up a conversation:
- “Hey! Just wanted to wish you good luck today on your presentation!!”
- “Hey there! How was your trip last week? Did you have a blast?!”
- “Just checking in to see if you heard back from any of those jobs you applied for?”
- “Hey, how is your aunt? Keeping her in my thoughts and hoping for a quick recovery.”
14. Spice things up with a flirty text
Once you and a guy are no longer just friends or if he’s earned the official title of your boyfriend, a flirty or playful message from you can brighten his day up.[3] A sense of humor is a quality a lot of guys appreciate in people they’re dating, and funny texts are also great ways to keep in touch with a guy. For example, try:[5][6][7]
- Sending funny memes or GIFS
- Referencing an inside joke
- Sending a cute message of something that made you think of him
- Using more emojis to make a text message more fun or friendly
If you want to spice things up, you can always get a little flirtier or more explicit, but just keep in mind that you can’t unsend a text or pic. For example, sexts and nude selfies are often a source of remorse for people when relationships end or don’t work out. Unfortunately, explicit texts or photos being shared online is an increasingly common problem, so be wise about what you send.
15. Ask about what they’re looking for in a relationship
At some point, it’s important to have an open conversation about what kind of relationship you’re both looking for. It’s up to you to decide when to have this conversation. Some people prefer not to waste time and are really upfront about what they are looking for. Others avoid these conversations until they feel certain they’ve met the “right one.” Some try to put it off for as long as possible because it requires being vulnerable, which is hard for a lot of people.
While vulnerable conversations are hard, not having the conversation can be even worse. A recent survey found that the number one barrier for daters is finding someone who’s looking for the same kind of relationship as them.[1] For example, if you’re looking for something serious, but he just wants to hook up, it’s better to know this before you get too invested in the relationship.
Final thoughts
Talking to guys can be difficult, but having some good topics and ideas about things to talk about can help. Sometimes, these will help to keep conversations flowing in ways that feel natural, instead of conversations that feel forced, awkward, or one-sided.
If things are getting serious with a guy you’re seeing, your conversations will probably get deeper and more meaningful. At some point, it’s also important to clarify that you’re on the same page with a guy you’re seeing, especially if your goal is to find a new partner or get into a committed relationship.[5]
Common questions
If a guy keeps a conversation going, does he like you?
When a guy you’re chatting or texting with keeps a conversation going, it usually means he’s interested in you or likes you, but it doesn’t necessarily mean he’s interested in you romantically. For example, a guy might be interested in hooking up or making new friends.
What happens if you run out of things to say to a guy?
If you run out of things to say during a conversation with a guy, don’t panic. Saying, “My mind just went blank” or “I just forgot what I was going to say” can be a simple way to make it less awkward and buys you time to recover.
What if a guy stops responding to you on a dating app?
Being ghosted is hard, but it happens to a lot of people. If this happens, send one or two messages, but don’t keep texting if you get no reply. Instead, focus on guys who are more responsive.
