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The Simple Secret to Beginning Compelling Conversations

There's nothing that amuses me more than hearing someone give the advice that you can begin a conversation by saying anything… While technically true (and far better than not starting a conversation at all as the alternative), there are good ways and bad ways to start conversations…

In the past 5 years, I have started conversations with over 20,000 people and trained people to do the same in situations related to romance, networking, sales, and generally socializing. I've tried a lot of things. Some worked. A lot didn't. Now it's your turn to start getting conversations off to a roaring start with my best practices around beginning conversations.

The Open

I label the first words you use to begin a conversation, the Open. The purpose of the open is to create (or open up) a dialogue with a person where there was not one before. You can consider a conversation successfully “opened” when the person you are talking to replies. The conversation is now moving, and all it takes is a single phrase (see the end of this article) to broaden the conversation from a quick exchange to a broader emotionally charged conversation by following the Conversational Formula.

The Three Ways Every Conversation Begins

There are three ways to start a conversation with anyone:

  • She starts a conversation with you
  • You start a conversation with her
  • Someone introduces the two of you

While you can nonverbally influence a girl to open you or convince someone else to introduce the two of you, we are going to put our focus into how you can start the conversation with her because you have most control over this option. Remembering the goal that we just want the conversation to get a good start–meaning she responds to us in a way that the conversation can broaden beyond the initial topic–here are your 4 approaches to beginning a conversation in order from most advised to least advised and reasons for doing each…

The Compliment

The compliment is one of the easiest and most powerful ways to begin a good conversation. This is when you make a positive remark about something a girl has likely put time, effort, or thought into, such as her hair, clothes, shoes, and even her pet. Compliments will almost always be taken positively and will put the person you are talking to in a better mood…

As you start to understand what a girl values and how she thinks, you are going to develop an intuition for what things you can compliment each girl on. The simple question to ask yourself when you see a girl who you would like to start a conversation with is…

What is it about her that stands out that I find interesting, intriguing, or extraordinary?

Then go up to that girl and compliment her on that thing about her. With a little trial and error, you will quickly fine tune your observational muscles to pick out the right thing to compliment a girl on.

Here are some examples to get you started…

Compliment on Her Hair

Oh wow! I love your hair.
Wow! I love the bangs. 
(girl with bangs)

Note: Women put remarkably more time and effort into their hair than men. By complimenting women who have nice hair, you are recognizing something that most men completely ignore. You become a person “in the know” and will have more rapport with these ladies because you have revealed you appreciate a part of their world most men do not notice.

Compliment on Her Pet

Aww… that is such an adorable puppy

 Note: This is reference to any dog of any age… just about every girl likes to think of their dog as a puppy.

Compliment Her Style

Oh wow! I love the frames! (Girl with glasses)

Note: People cannot choose whether they have good vision or not. They can choose the frames of the glasses they wear. Complimenting the frames is relatively specific and validates them for choosing a cool set of frames.

Haha! I love the shirt! (When wearing a graphic tee you like)

Wow! Nice tattoo design!

Note: If they have a tattoo, 95% of the time it means something to them and about 80% of the time they are still happy with having it. Either way, you are picking out a part of her and recognizing it.

Final Thoughts on Compliments

  • Sincerity is an absolute must! This is why I encourage you to start thinking for yourself about what truly intrigues you about a given girl (aside from her beauty). When you are approaching her about something you genuinely mean, she will take the compliment well.
  • It's all about practice! The beauty of compliments is they'll never be poorly received, which is why I encourage guys to start with compliments when they are practicing talking to girls. One super easy way to get very good with the art of complimenting is using Tinder. Unlike in person, on Tinder you have an abundance of time in which you can look at her profile and find those things that jump out at you. Then send her a message about it! (Check out the Top 5 Messages that Work 80% of the time on Tinder here [AAAA])
  • Getting attention is always important before saying the compliment and with any open. This is because she may not be paying attention to you before then and will not hear the compliment if you say it before she is listening to you. To get her attention, I'll say, “Excuse me” or “Oh wow!” or “Haha” or something else relevant to the situation and the open I am about to say.

The Observation

Making an observation about something the girl is doing or that is going on in the nearby area is the best way you can begin a conversation. It's also a little more difficult than the compliment. Being observant of what's going on around you will make you very good with this conversation starter before long. When you get this right, you seem very perceptive and present, two attractive qualities.

Observations are very situation-specific. Here are some examples to spark your own creativity…

Observation at Social Gathering

Oh! So this is where the party’s at! (Said to one or more people in a group. Works best when group is high energy)

Observation on Weather

Oh my god! It's so cold right now! I'm jealous you have so many layers on!

Note: Obviously super situational specific. Playfully mentioning that you are jealous about them for being better than you at something will almost always go well because it's evident you're joking around.

Observation on Just about Anything Notable that Just Happened

Oh wow! Did you just see that too?
Oh my god! Did that seriously just happen? You saw that right?

Note: The thing you are witnessing doesn't have to be absolutely remarkable. It's all about your delivery that will carry that observation.

The Functional Open

For people super nervous about beginning conversations with strangers, start with the functional open. It's not nearly as amazing as the compliment or the observation, but you will at least get the conversation started. Also this is a great way to warm yourself up if you are at a club, event, or out and you are just trying to get your socializing muscles warmed up a little. The main reason I do not like the functional approach too much is because it also assumes very little rapport and you place yourself in the frame of someone uninformed or not fully aware of his surroundings. Also the functional does not really open a dialogue. As soon as the question is answered, the dialogue is technically finished. All this being said, you can still overcome this minor rapport issue and barrel through to a broader conversation rather easily by following the suggestions further in this post.

A functional open is any simple informational question usually about the surrounding area that just about anyone would answer. These include asking for the time, directions, and store hours of operation among many others.


Functional Time

Excuse me… Do you have the time?

Functional Directions

Excuse me… Do you know where the nearest Starbucks is?

Functional Hours of Operation

Excuse me… Do you know when the store opens?

The Direct Open

The direct approach is my least favorite approach but so many guys are addicted to this strategy and do it so badly that I should at least bring it up to give them the best odds of getting this thing to work. Hopefully you'll be inspired by the other strategies in this article, please realize that going up to a girl and saying she is beautiful is a terrible strategy overall. She has heard this plenty of times and probably doesn't exactly know how to react to your statement because whether or not she is interested, it's an odd comment and there's a high chance she's had a guy be volatile to her in the past when she was not absolutely flattered when he catcalled her.

Additionally when you go direct, you are putting yourself completely out there, and if she is not interested in you for any reason, your chance at appealing to her basically vanishes. You're far better off opening with a compliment or observation and then following the Conversational Formula.

The only time being direct is an okay strategy is when you don't have enough time to actually have a conversation. Perhaps you are about to run off to work or class or the gym and cannot come up with a quick observation or compliment, then sure say the direct thing. This is the most common line I've ever heard for a direct open:

Direct Example

Excuse me. I saw you walk by and thought you were cute and would be kicking myself if I didn't say, “Hi.” I'm [your name]. What's your name?

Note: You will get more positive responses by using a word like “cute” than “hot.” You still will want to broaden the conversation after this statement.

After the Open

As soon as the girl responds to your open, congratulations! You have successfully begun a dialogue! The next step is to broaden the conversation. No matter what you begin the conversation about–whether about her hair, something going on around you, her looks, or simply for directions–if you continue talking about that topic, you are going to fall on a single subject conversation…

The problem with this is that eventually, the conversation will run flat and then it's much harder to bring up something new to say once the conversation falls flat. Usually before you have a chance to, the person will excuse themselves and continue about their day.

To prevent the conversation falling flat, you need to broaden the conversation and then follow the Conversational Formula.

Here's what you say to broaden the conversation as soon as she replies…

The Transition

Oh wow! You're actually really friendly! Where are you from?

From here, follow the Conversational Formula and you are golden!

The Other Two Beginnings

We covered how you begin a conversation. What if she begins the conversation with you or someone else introduces the two of you?

Well, it's pretty simple… First, decide if you actually want to get to know that person… If you do, then just say the Transition above and have a compelling and stimulating conversation following (you guessed it) the Conversational Formula!

That's what I've got on getting things going. You'll notice no pick up lines of any kind. That's because a 1 liner is never going to work to capture a girl's interest as more than amusement. The true way to connect and be with someone lies in the conversation.

How do you like to open up conversations?

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