How to Talk to a Guy You Like (Even if You Feel Awkward)

Talking to strangers can be a challenge at the best of times. Talking to a guy you like is often much more intimidating, but it doesn’t have to be.

Here are our top tips to help you talk to any guy you’re interested in, with minimal awkwardness.

Sections

  1. How to start a conversation with a guy you like (in person)
  2. How to keep a conversation going with a guy
  3. What to talk about with a guy via text
  4. How to keep a conversation going on a first date with a guy
  5. Common questions

How to start a conversation with a guy you like (in person)

Starting a conversation with a guy you don’t know can be scary. Talking to strangers risks rejection, especially in a public setting such as a bar. Here are some of the best ways to start a conversation.

1. Stay calm

This can be easier said than done, but the more you can calm yourself down before talking to a guy you like, the easier the conversation will usually be.

Take a few deep breaths and spend a moment paying attention to how your body feels. Notice any muscles that are tense and allow them to relax.

2. Start a conversation by saying “hi”

Lots of guys complain that they’re always expected to make the first move, but it doesn’t have to be that way. Rather than focusing on how to get guys to talk to you, try to feel comfortable approaching them. Saying hi and smiling might be all the ice-breaker you need.

Being told to “just say hi” might seem like being told to ‘draw the rest of the owl’, so here are some steps to saying hi.

  • Make eye contact and smile as you approach
  • Take a deep breath
  • Say “hi” and tell him your name
  • Have a back-up question ready in case he doesn’t continue the conversation. This might be “Are you new here?” or “What does it say on your t-shirt?” It doesn’t really matter what the question is as long as you can ask something to show that you’d like a bit more conversation.
  • Have an exit phrase ready. This is a graceful way to get yourself out of the conversation if it feels awkward. Simply saying “It was nice to meet you” gives you a way to end the conversation gracefully.

Just saying hi and having a chat with a stranger might seem like too much of a challenge if you’re shy, and that’s OK. Check out our guide on how to stop being shy in social settings for advice that can help you.

3. Be prepared for rejection

When you start a conversation with someone new, there is always a chance that they won’t want to talk to you. It can be helpful to prepare yourself so that rejection doesn’t feel so bad.

Before you approach him, remind yourself that he might not want to talk to you right now for reasons that have nothing to do with you. He might be busy, worrying about something in his personal life, or have had a rough day at work. If he doesn’t want to talk to you, it doesn’t mean he dislikes you or that you did something wrong.

If you’re nervous about rejection, check out our guide to learn how to tell whether someone wants to talk to you.

4. Practice approaching other people

The more you approach different people for conversation, the easier it can be to understand that some people will want to talk, and others won’t… and that’s OK.

Starting a conversation with a guy you don’t know might feel different from approaching other people, but the skills you need are the same. Try starting a conversation with one stranger each day, maybe on your way to work or in the checkout line when buying groceries. This can help build conversational skills to help you start talking with the guy you like.

If you struggle to approach anyone for conversation without being awkward, we have a whole guide devoted to learning how to not be socially awkward.

5. Pay him a compliment

If you’re attracted to a guy, there must be something about him that you like. Hopefully, that will make it easier for you to find something to compliment him on.

Try to keep your compliments specific and personal. Compliments based on stereotypes, in particular, can leave people feeling worse than saying nothing.[1]

Guys don’t get as many compliments on their appearance as women,[2] so telling a guy you like his hair or his t-shirt can make you stand out. Compliments on someone’s appearance tend to come across as signs that you’re interested in them.

You might worry that he will feel uncomfortable about receiving a compliment, but studies show that people and more comfortable receiving compliments than we expect, and they enjoy them more.[3]

Giving a compliment isn’t just in the words you say. Your tone of voice can also show that you’re impressed with someone. Just saying “You seem to know your way around” can be a compliment if said in the right tone of voice.

6. Don’t put him on a pedestal

Putting a guy you like on a pedestal can make it harder for you to approach him and can actually be uncomfortable for him.[4] Talk to him naturally by remembering that he’s a normal person.

Remind yourself that you’re only crushing on a guy once you talk to him. Until then, you’re attracted to your image of him. Having the courage to start the conversation can help you start to get to know who he really is.

How to keep a conversation going with a guy

Let’s say that you’ve started talking to that cute guy, whether he’s a friend or a new acquaintance. You might find that your mind is racing, worrying about whether your hair looks OK, whether you’re laughing too loud, or if the conversation is going to fizzle awkwardly.

Here are the best ways to carry on a conversation with a guy you like.

1. Smile

Smiling when you’re talking to a guy you like does two things. It shows him that you are enjoying the conversation, which makes you appear warm and approachable.[5] It can also help you to relax into the conversation.[6]

If you feel awkward about your smile, try our tips to help you build a naturally dazzling smile.

2. Make eye contact

Making eye contact shows that you’re interested in what the other person has to say, but if you’re talking to a guy you like, it can be even more important.

Studies show that making more eye contact can create a sense of intimacy and increase romantic feelings.

Making lots of eye contact can feel intimidating, so go slowly. Start by holding eye contact for just a moment longer than you normally would, and slowly increase how long you feel comfortable holding his gaze.

3. Touch him a little

We tend to make more physical contact with people we are relaxed around and those we trust. Making physical contact with a guy can show him that you’re enjoying his company and that you trust him. You could touch his arm or gently push on his shoulder.

This can be another piece of advice that is difficult to follow. Being attracted to someone can make you hyper-aware of any time you touch them, which then makes it feel awkward and forced. Try to use low-impact touch to begin with, such as a high-five.

If you’re a girl, try to remember that it can be even more difficult for him to be the one to touch first. He might be worried about being too “handsy” or coming off as a creep. One great strategy is to take the uncertainty out of the issue by being overt about your use of touch. If you’re feeling awkward about hugging him, for example, try asking, “Are you a hugger, or a handshake guy?”

If you’re a guy, it can be even more complicated to work out when it’s ok to touch and when it’s not. Straight women are generally given a lot more license to touch others than men are, however unfair this might be. Try not to initiate touch more than once or twice in a row without him reaching out in return.

4. Practice small talk

Lots of us don’t enjoy small talk, but it’s an important skill. Small talk lets you start to get to know someone in a way that feels safe for both of you. It’s a chance to show that you are interested in communicating with them more and that you can be trusted to be polite, fun, and respect their boundaries, which builds trust. The more comfortable you are talking about minor topics, the easier it will be to keep a conversation flowing.

The fastest way to get better at small talk is to practice a lot. Try making small talk whenever you get the chance. You’ll probably find that you get better at it surprisingly quickly. If you’re struggling, or if the idea of practicing small talk makes you anxious, we have a whole article devoted to how to build up your small talk skills.

5. Offer personal information

If you’re starting to talk to a guy you like, you might be excited to learn everything you can about him. This can leave him feeling like he’s being interrogated rather than having a relaxing conversation.

Research has shown that the fastest way to feel close to someone is by offering small bits of personal information and responding to the personal information that they give you.[7] To begin with, you can offer information that’s only slightly personal, such as “I have a pet dog” or “I like cycling.” Over time, you can offer information that’s more meaningful to you, such as your dreams for the future.

The aim is to offer information and wait to see whether they reciprocate. Only say something more personal if they’ve said something equally personal to you.

The ideas about how to become closer to your friends are also useful for becoming closer to a guy you like.

What to talk about with a guy via text

Lots of us are meeting new guys via dating apps, such as on Tinder or on Bumble. Whether you first meet someone in person or online, the chances are you will spend a lot of time talking to them via texts or messages. Here are our best ideas to keep the conversation flowing naturally when you talk to guys online or via texts.

1. Reply promptly

Slow replies don’t always mean that you’re not interested in a guy. You might just get distracted doing other things and then realize you meant to reply 3 days ago. Unfortunately, slow replies do feel like a rejection.

Try not to read texts until you’re in a position to reply. If that doesn’t work for you, try setting a reminder on your phone to reply later that day.

Don’t aim for perfection. You might procrastinate because you want to get your message exactly right. Think about how you feel when you receive a text from him. You’re probably just excited to hear from him, rather than analyzing every word. Just say what you want to say without overthinking it too much.

2. Ask questions

Keeping a text conversation going means giving the other person something to answer or reply to.

This is why the guys who pop up in your DMs saying ”Hi. You’re cute” are so irritating. They’re not offering anything to the conversation.

If you’re not sure what to ask, try giving a piece of information about yourself and then asking, “How about you?” For example, you could say, “I’m going hiking this weekend, which I’m really looking forward to. How about you? Any fun weekend plans?”. Here is some inspiration for conversation starters and questions to ask a guy you like.

3. Flirt a little more

Most people are a little bit more flirty online or over text than they are in real life.[8] It might seem strange, but being your normal self can seem standoffish over text but warm and flirty in person.

Try to up your flirting during text conversations. This might be by dropping in casual comments about him looking good, teasing gently, or making suggestive comments. Here you can find some subtle ways to show you like them as more than a friend.

4. Suggest moving to a different medium

Even if your text-based conversations are going well, you will usually want to move the conversation to some kind of face-to-face interaction eventually. If you’re struggling to talk without being awkward over text, you might want to suggest moving to a different form of communication sooner.

You don’t have to jump directly from texting into meeting up at a party. Think of how you would feel most comfortable talking. This might be on the phone, via Facetime or Zoom, or meeting up for a walk or a coffee.

It might feel scary to be the one to suggest a more personal way of talking but remember that one of you will have to do it. It’s no less scary for him just because he’s a guy. Being the one to make the suggestion also lets you suggest the approach that works best for you.

How to keep a conversation going on a first date with a guy

If you’ve managed to get to the first date stage, great job. You’ve overcome the first hurdle, and there’s probably some attraction between you. Conversation during a first date is about getting to know the other person and letting them get to know you. Here are some tips for how to keep the conversation going on a first date.

1. Be honest and be yourself

If things go well during a first date, you’re probably hoping for more. The date is both of you trying to work out whether you’d like to spend a lot more time together, so it’s important that you show the real you. Try to focus more on being honest than on being impressive. Remember, you don’t need to be perfect to be loved.

This doesn’t mean that you shouldn’t make an effort. In fact, when you try to make a good impression, people get a more accurate understanding of who you are.[9]

Sometimes, you might be tempted to tell a white lie to make a better impression, but you usually shouldn’t. For example, if he tells you he loves Ska music, don’t say that you do too unless it’s true. Instead, try saying, “That’s really cool. It’s not my taste, but I love how enthused you are about it.”

2. Be generally positive

You don’t want to be fake, but try to focus your conversation on the more positive things in your life. This will make you seem more upbeat and enjoyable to be around and keeps the conversation going without awkward silences.

You can touch on more negative topics, but try not to make them the focus of your conversation. For example, you might mention that you’re not that close with your family, but it’s usually better not to go into long anecdotes about how your mum started a huge argument during that holiday in Texas.

3. Ask questions

Keeping a conversation going, especially on a first date, is about balancing giving information about yourself with showing an interest in the other person. This means you need to ask questions without letting it feel like an interrogation.

One great way to do this is to ask for more details about something he’s already talking about. For example, if he’s telling a story about a funny conversation, you can say, “Oh gosh! What did she say then?”

Try to focus on asking open-ended questions. Closed questions can be answered with a single word, usually yes or no. This can leave the conversation feeling stilted. Open questions, such as “what do you like about it?” or “what have you been up to today?”

We also have a more detailed breakdown of how to use questions to keep a conversation going.

When you ask him questions, try to be genuinely interested in the answers. Don’t ask for details about his workday if you really don’t care that much. Ask about the things that matter to you or that interest you.

4. Avoid topics that make you rant

A first date is a time to get to know each other. Having a long rant about a topic you feel strongly about might be enjoyable, but it’s not giving him a chance to learn much about you as a person. It can also make you come across as an angry person.

Some other topics of conversation should also be avoided, but this will partly depend on your local culture. For example, in England, you don’t typically discuss your salary, and especially not on a first date.

5. Focus on things that you share

Talking about things you have in common can be a great way to keep a conversation going. Try to find topics that you’re both interested in, and elaborate on shared experiences.

Remember that you don’t have to have the exact same tastes to find shared things to talk about. If he likes going for runs and you like swimming, you might both love the first cup of coffee after your exercise.

You can also try to find connections in terms of how you feel about activities rather than the activities themselves. In the example above, you can talk about how you both love the freedom of being able to exercise alone in the mornings before everyone else is awake.

6. Speak to him as if he’s already a friend

Friendship and trust are at the heart of all relationships. If you’re on a date with someone, you’re trying to build a friendship as much as you are trying to create chemistry.

Show that you like and trust him by talking to him as if he’s already a friend. This means that you can crack jokes and enjoy the conversation. This can also make it easier if you do mess up a little.

It can be helpful to treat him slightly better than you do other guys. This sends a subtle message that you like him more than you do other people. If you just want to be friends, here’s our guide on how to become friends with a guy.

7. Focus on the “right now”

No matter how well a first date might be going, it’s almost never the time to start confessing your feelings or talking about marriage and babies. Avoid putting too much pressure on the conversation (and yourself) by focusing on the date you’re currently having. This can make it easier to keep the conversation going.

Common questions

How can I talk to a guy when I feel awkward just saying hi?

Overcome awkwardness talking to a guy by reminding yourself that he probably can’t tell how you feel about him.[10] Try to be friendly rather than trying to impress him. The more you practice talking to guys you like, the less awkward and anxious you will be.

How do I talk to him if he is shy?

Make it easier to talk to a shy guy by respecting his privacy and boundaries. Shy people often don’t like to open up about themselves, so don’t bombard him with questions. Instead, try making opportunities for him to talk about himself without pressure. Focus on making him feel comfortable.

How do I get better at talking to guys?

The fastest way to get better at talking to guys is by practicing. The more you speak to different men, the more you realize that talking to men isn’t very different from talking with your female friends.

How do you know if a guy likes you?

The biggest signs that a guy likes you are that he tries to spend more time with you, he looks at you and makes eye contact, he touches you more than other people, and he pays attention to you in a group.

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Natalie Watkins writes about socializing for SocialPro. She holds a B.A. in Experimental Psychology from the University of Oxford, an M.S.c. in Cognitive and Clinical Neuroscience from the University of London, and is currently in her final year of an MSc in Integrative Counselling at the University of Northampton.

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