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How to Start a Conversation with Someone You Like

Updated on October 11, 2016
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Sadie Holloway is a workshop facilitator who teaches interpersonal communication skills to help people strengthen their relationships.

These tips on how to start a conversation with a guy you like will give you the confidence you need to finally approach him and get to know him better.

Start with small talk and move your way up.

Is there a guy at work or school you want to talk to, but you're too shy? Check out these easy tips on how to start a conversation with him!
Is there a guy at work or school you want to talk to, but you're too shy? Check out these easy tips on how to start a conversation with him!

What can you do to boost your confidence when you’re nervous about talking to a guy you like? There are a number of ways you can calm down and approach him without losing your cool. The secret to starting and maintaining a conversation with someone, especially someone you like, is to understand and notice how a natural conversation progresses from one level to the next. There are four distinct conversational phases that people pass through as they develop a relationship with someone they’ve just met.1

|making small talk and chatting about the weather or your mutual surrounding is an important part of the evolution of a conversation between two strangers.
|making small talk and chatting about the weather or your mutual surrounding is an important part of the evolution of a conversation between two strangers. | Source

Bonus Tip: If you want to have a good conversation with that guy you like, pay attention to your body language and voice and vocal projection. According to Albert Mehrabian's work studying interpersonal communication, how your voice, words, and facial expressions influence how likable you are perceived can be weighted as such:

Total Liking = 7% Verbal Liking + 38% Vocal Liking + 55% Facial Liking

Source: Mehrabian, A. (1981). Silent messages: Implicit communication of emotions and attitude

The first phase of striking up a conversation with someone is known as making small talk. Small talk, while often dismissed as trivial, is actually a very important aspect of getting to know someone. Small talk often includes light subject matter such as the weather, a comment about the events surrounding the two speakers, and current events. Small talk is ideal for striking up a conversation because it doesn’t require extensive knowledge about a particular subject matter.

Small talk is an important part of the getting to know you phase because it establishes a mutual interest in having a conversation. If the guy you're interested in walks away when you make a simple comment about the weather, he’s sent you a message that he’s not interested (or able to engage) in a conversation with you at the moment.

During the small talk phase, neither person involved at this point is committed to a full-on conversation. If, for whatever reason, it becomes clear that there's no chemistry and the conversation won’t be going any further, nothing significant has been lost. Since small talk isn’t about making grand declarations or emotional disclosures of personal information, either party is free to end the conversation and politely move on.

Will starting that conversation with someone you like be worth the risk of rejection?
Will starting that conversation with someone you like be worth the risk of rejection?

As your conversation moves from the initial greetings and starts to gain momentum, it’s important to ask questions that allow the other person to give you more than a yes or no answer. Most open-ended questions begin with the words what, how, or why. Open-ended questions, that is questions that natural elicit a more thoughtful, detailed answer are the heart of a fun, easy-going, easy-flowing question. Most people like to talk about themselves rather than a complex topics when meeting new people because they already have all the answers. When you ask someone questions about himself, he doesn’t have to remember facts or bits of trivia. He doesn’t have to prove that he has a vast store of academic information tucked in his brain. He just has to show you that he knows himself well and takes pride in who he is.

Move out of your comfort zone. You can only grow if you are willing to feel awkward and uncomfortable when you try something new.

— Brian Tracy

The next phase of a smooth-flowing conversation is the sharing and learning simple facts about each other. After the small talk phase, when you’ve established a mutual interest in talking to each other, you can begin to share some details about yourself that are not too personal. This phase of the conversation is also a good time to start asking open-ended questions that help the two of you establish common interests. For example, you could ask him about his occupation or what he likes to do in his spare time. As each of you share small bits of information about yourself, you’ll hopefully find things that you can talk about in greater detail. For example, you make find out that you both like to cook. This could lead to a conversation about favorite foods, recipes, places to eat, and so on.

The third phase of a successful conversation with a guy you like will likely involve the two of you sharing your thoughts and opinions on various issues. You may talk about politics, express an opinion on a current event, or offer a viewpoint on an issue you feel strongly about. Some people tend to be cautious about talking about politics with strangers, but if you have been listening carefully you’ll likely have a sense of whether or not the two of you are ready to start sharing your thoughts on issues that are a little more complex than how nice--or as it may be, lousy--the weather is.

Finally, if the conversation is moving naturally, you may find yourself discussing feelings that are more personal or private that merely expressing an opinion or strong viewpoint. For example, he may tell you about a personal family matter he is coping with right now, such as a sick relative. Not every conversation gets to the fourth level of depth. You and this fellow may not start talking about more personal matters until you have had a few conversations that glide smoothly from small talk (phase one) through to sharing and opinion (phase three) before you have a conversation that gets all the way to phase four.

Now that you know the various depth-levels of a conversation, you’ll have a better chance of starting and sustaining a conversation with someone you are interested in. Knowing the different phases that are a normal part of the conversational process will help you avoid coming on too strong (i.e.; sharing personal information too soon) or misinterpreting his availability to carry out a conversation with you at this time. If the conversation doesn’t progress past small talk then you needn’t worry about having spilled your heart out to someone who wasn’t interested. Likewise, now that you now the various stages in a smooth-flowing conversation, you will be able to gauge his level of social and emotional intelligence. If he, for example, jumps from small talk right into a deeply divisive political debate.

Starting a conversation with a guy you like is easiest when you have a positive attitude. If you genuinely believe that everyone has an interesting story to tell, whether or not you are interested in them romantically, you will find it easier to talk to people without getting flustered. Focus attention away from your nervous energy by showing the guy you are talking to that you are genuinely curious about his story.

Notes: 1. Interpersonal Communication: Conversing with Ease, Toastmasters International

Photos: Pixabay.com

Quotes: Brainyquote.com

Every relationship starts out with a single conversation.
Every relationship starts out with a single conversation.

Reminder: Always trust your gut. Although most conversations progress in a gradual manner from small talk to more personal disclosures, that doesn't mean you shouldn't trust your gut if something doesn't feel right. Even if you are trying to get out there and meet new people in a effort to overcome shyness, don't force yourself to stay in an uncomfortable situation if you are getting a bad vibe from someone. Part of being a good conversationalist is maintaining healthy boundaries with people you've just met.

Poll: What's your social style?

Do you prefer to initiate conversations or have someone approach you first.

See results

© 2015 Sadie Holloway

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