How to Start a Conversation with a Guy Effortlessly

Communicating with the opposite gender is complex and sometimes anxiety-inducing. Regardless, it’s not something you can go without almost on a daily basis.

Most girls, if not all girls, have been in a position where they’ve desperately wanted to strike up a conversation with a guy but found themselves at a loss of word. After all, men seem like such an impossibly foreign species.

In most scenarios, what keeps girls from striking up a conversation with a guy is the common lack of experience in this area. Guys usually come up to you, so this may be a new skill you want to learn.

Congratulations on making this step and taking matters into your own hands!

If you’ve wondered how to start a conversation with a guy, then there is no need to worry. In this article, we’re going to provide you with some exclusive tips on how to become a master at striking up conversations!

How to start a conversation with a guy?

Small talk works.

You might think that small talk is the worst way to begin a conversation, but in most circumstances, small talk is an excellent way to make a move!

Asking for a small favor such as directions, opinions, or even commenting on the weather is completely fine.

The best way is to initiate the small talk and then lead the conversation towards something a little less generic.

If you tend to struggle with even that, then asking questions that fall into the dimension of small talk is also a safe bet. Here are some great (and simple!) ideas that you can use:

  • Talk about the weather. It’s a classic for a reason. If it is a cold day, you can say something playful, like – Is it just me, or a trip to Hawaii would be a life-saver now?
  • Compliment on a piece of clothing they are wearing. It’s simple, and it works – Loving your shoes! Always a pleasure to meet someone who knows their style.
  • Strike up a conversation at work. You can always complain about a busy week – Don’t you feel like there is so much more work this week?
  • Drop a casual cliché while you are at a park – It sure is a wonderful day to be outside, isn’t it?

The point is – you don’t have to come up with something incredibly smart or interesting. Your main goal is to start a conversation, and the good old tricks have been doing the job for decades.

Steer away from stereotypes.

A redhead girl making a funny facial expression.

The most common issue that accompanies our difficulty to talk with the opposite gender is that we often associate certain generic assumptions with them.

You may think you cannot start a conversation with a guy because all he might want to talk about are cars, sports, or some other topics you know nothing about.

All people are beautifully diverse, and there is a chance you are both interested in the same things. Even if you are not, it may lead to an even more interesting conversation!

Keep your options open and talk about anything that interests you because chances are, the guy you’re interested in might have a draw towards the same topic. This approach will help you stay comfortable and in your lane as you navigate the conversation.

Offer a compliment.

Guys enjoy praise too!

If you think about it logically, why would any person, regardless of gender, dislike a compliment?

Making a simple compliment about what a person is wearing, their hair or even their eyes is completely a safe bet. Guys enjoy the praise and are quick to pick up interest from your side this way.

Of course, you need to make sure that the compliment is appropriate to the interaction level you’re engaging in. If this is a guy you barely know, then be sure to know what kind of praise is okay and not too forward. If you’re somewhat familiar, you can be a little more open but feeling the conversation is completely up to you.

Are you still wondering what you could compliment him on? Here are a few suggestions that he won’t be able to resist:

  • Say that you feel lucky to be spending time with him. That can make a person feel special and appreciated.
  • Compliment his knowledge on a certain topic. The chances are – if he knows a lot about something, he is passionate about it and will appreciate the praise for that.
  • Mention his kindness if he is a nice person (and he better be if you are interested in him!). People who care about others rarely get enough appreciation for it. Show him that you care!
  • Express your amazement with how he handled a certain situation. Guys love to be proactive, make decisions and look after you. If you show your appreciation, he will feel good about himself immediately.
  • Call him your hero if he went out of his way to make your day amazing. Sometimes a simple ‘thank you’ is enough, but why not say more if you have the chance? Everybody loves being the hero!

Use your sense of humor.

A couple having fun and laughing.

Humor is a very enjoyable trait and one that guys especially like in women. When trying to start a conversation with a guy, try saying something funny.

Yes, we know it’s not that easy to do. That’s why Witty Companion is here – to help you be funny effortlessly! Just check out our humor section, and you will see improvements in no time.

Humor will not only spark his interest but also make the conversation fun and lighthearted. It can quickly lead to friendly banter. Banter is an excellent way to keep things going and bond fast with people.


It shows that you two are comfortable enough with each other that you can get away with a few friendly jabs. Just think about it – how often do you do it with your friends?

Using your sense of humor is also a safe bet to pass on the message that you are not necessarily interested but habitually an outgoing person. This makes it easier to avoid an uncomfortable situation if the guy you want to talk to may not be interested in reciprocating.

Nevertheless, being funny is a very reliable way to start a conversation with a guy (or anyone for that matter) if you can pull it off.

Radiate confidence and enjoy yourself.

A confident young woman.

A key element is to make sure your body language and expressions communicate confidence and comfort.

While most of us may be struggling with confidence issues, it is not as hard as you may think it is. Just check out our guide on confident body language here.

If you can pull that off, whatever you say is a good conversation starter.

For instance, imagine uttering the perfect opener but shaking while doing so. On the other hand, imagine saying something silly but owning it completely. What do you think would work better?

In essence, focusing more on how you project yourself is a fool-proof way to improve all areas of your social skills.

In contrast to common belief, guys like confident women who can hold their own. So, trying to integrate this principle the next time you try to start a conversation with a guy can be an excellent way to portray a good image.

How to keep the conversation going?

You have approached him, and it went well! Yay, you!

What do you do now?

Once you start talking, here are some great topics that you can talk about to make the conversation interesting and even unique:

  • Find out if he is a dog person or a cat person and why.
  • Talk about the earliest memories you both have – most people have interesting childhood stories. Still, they rarely bring them up in a conversation.
  • Ask him about the small joys that bring light into his life. This question can lead to some pretty wholesome answers.
  • A great question that you can ask if you are bold enough is – What is the one thing about you that most people would be shocked to find out?
  • People love talking about themselves. Ask him to tell you what is his favorite thing about himself. It’s bound to lead to a fun answer.
  • Following the same logic – you can ask him to describe himself unusually. What do we mean by this? Ask him what single song/color/movie would he use to describe himself. It gets people thinking in no time.
  • On some occasions, it may be interesting to see if he can tell you what his name means. There are quite a few people who cherish the meaning of their name. However, keep in mind that most of us don’t know much about it.

Your Turn

Conclusively, learning how to start a conversation with a guy boils down to sticking to what you know best and general experience. We hope that we managed to shed some light on the topic and that you picked up on a few good ideas here.

What is your favorite conversation starter?

Let us know by leaving a comment below – we would love to hear from you!

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