“Hey Rob, how do I break the ice with a girl? Holding conversations whether it’s small talk or some really deep stuff is pretty easy, but my real hurdle is overcoming the initial awkwardness of the introduction.”
With every workshop and Dating Mastery Class cycle, I’ve consistently gotten a variation of this question on how to break the ice and create the bridge from the initial introduction to creating a connection with a girl you’re attracted to. After a few years of doing this, I had to take some time to reflect and find a way to clearly articulate this concept, since at this point in my life it’s become instinctive.
That doesn’t mean I can’t empathize with someone who doesn’t have experience with women or general people skills for that matter, as it was also something I struggled with at one point in my life. I used to think that trying to start conversations with random strangers, especially attractive women who I had no relationship with whatsoever, even past a surface level and platonic relationship, would ever be possible.
One reason why men have such a hard time approaching a girl and even opening or starting a conversation with her has to do with the dreaded approach anxiety. If you’re still struggling with approach anxiety, I recommend that you take a look at part one and part two of our approach anxiety series to better understand it and implement some of the tactics and strategies to effectively manage your emotions and overcome it.
4 Types of Openers You Can Use to Make Every Conversation Stick
There is a lot of really confusing and misleading information out there presented by dating coaches, sleazy pickup artists, and so-called “experts” who claim that you need to do a lot of things or always have the right thing to say to break the ice with a girl who caught your eye, before you introduce yourself and have a conversation with her.
I’m not here to bash other systems or schools of thought when it comes to the topic of dating, but I will tell you one thing, it really boils down to sound judgment and a little common sense.
I’m not going to give you a list of pickup lines, gimmicky openers, or ridiculous lines you should say to a girl to break the ice with her. Instead, what I’m going to do is provide a conceptual framework for you to add to your communication toolbox.
The Functional Opener
This opener is a little indirect and subtle, but when applied effectively, can defuse and bring any girl’s guard down.
A lot of people ask me what I say to a girl to get a conversation going, and to be honest it’s as simple as asking for something random such as asking her for directions to the nearest coffee shop, what the time is, or if she has an iPhone charger.
Now, you’re probably scratching your head in confusion and that I should be honest and direct about my intentions. But after a few years of doing this and getting rejected God knows how many times, I decided to re-orient myself and focus on how I’m communicating with a girl.
That perspective shift came when Chris Luna and I were running a dating workshop for single women and men. I remember there was this stunningly beautiful blonde girl that was in the audience, asking tons of questions as she was feeling stuck and lost in her dating life.
For the few men who were part of and present in the workshop, I’ll never forget the moment when Chris wanted to make a point with a guy who was adamant on just directly opening a girl and telling her that she was sexy or cute.
Chris asked that beautiful blonde girl in the audience on how she’d like a man to approach her, introduce himself, and in a nutshell how to break the ice with her. He wanted to make a point with the men in the class and show them that going balls to the wall direct and taking the more macho approach isn’t always the best solution.
She said, “I want him to just talk to me and have a normal conversation without hitting on me or showing his interest only because of my looks.” To my astonishment, every girl who was present in the lecture nodded their heads in agreement.
A lot of women, especially attractive ones, get hit on and approached based on their looks or something that has to do with their physical appearance. While some women will respond well to forward advances, you’re cutting off a huge percentage of women who are in the gray area that we refer to as the “maybe zone.”
I’m not saying that you shouldn’t be forward with your intentions with a girl. The point I’m trying to make here is to be socially aware of your surroundings and her fears and insecurities. Girls and people in general don’t want to feel backed into a corner or forced to make a decision about someone or something. This is where the concept of “getting someone to a yes” isn’t actually a genuine yes.
To clarify this point, think back to the moments where you felt pressured to make a decision, only to regret it later. For example, imagine a really persistent and good friend of yours pressured you to come to an event because it was a valuable “business opportunity.” You show up to the event and realize that it’s a pitch for a multi-level marketing company that sells dietary supplements.
As everyone around you is signing up, you keep deflecting, saying that you want to think about it for a while, even though at the heart of it, you know that it’s a pyramid scheme. You eventually relent and end up buying in to not destroy your relationship with your friend. But you end up later resenting him and the people who pressured you into the buy in to become an affiliate.
It might not be your style and trust me, I’m a pretty straightforward guy as what I say is what I mean, but making the transition to indirectly asking a girl for something random and then moving onto a conversation was really difficult for me at first.
This type of opener can be used in practically any normal day-to-day scenario. What I mean by a “functional opener” is that is has a specific function and must be congruent with whatever situation you’re in when you see a girl you’re attracted to but just don’t know how to break the ice.
Don’t get over-analytical. Just keep two things in mind when you’re utilizing a functional opener:
- It must be congruent with your environment.
- Transition to a conversation right away based on whatever feedback or information she gives you.
Here’s an example.. This past Friday when I got done coaching the Dating Mastery Class, I walked over to the PATH station on 14th Street to get back to my car in New Jersey and go home. I was incredibly fatigued, as I had spent the week preparing the lesson plan for the class, and the last five hours teaching concepts, drilling, and making sure my students were doing their assignments and applying the concepts I went over with them.
At this point in the night, the last thing I wanted to do was socialize or talk to anybody. The only thing I had on my mind was to go home and pass out. As I entered the humid station, I saw this beautiful brunette standing in the corner waiting for the train. I quickly surveyed her surroundings and deduced that she might have been alone as there was no guy or group of friends directly next to her.
I positioned myself next to her, leaning my back on the wall as she had her back planted on the wall. As I was pretending to mess with my phone I turned over to her and simply opened her by asking her, “Hey, do you know what time the train is coming?” She replied, “Honestly, I’ve been here for 20 mins, I wish I knew, I can’t wait to get back home.”
At that point, I transitioned to a little bit of small talk about the train ride back and hoping that we didn’t get the drunk train. She laughed, and after a few minutes of talking about the train ride, it turned into some flirty bantering back and forth between us. I made a cold read and said to her, “You must’ve had a wild night.” She continued the conversation by saying that she came back from the Yankees game and was frustrated that they lost.
A switch went off in my mind, since I’m a huge Yankees fan, and I used the opportunity to toss in some banter about Aaron Judge. She bit on and we spent the next 5-10 minutes talking about her experience with the game, and getting to know each other, which led to more random topics ranging from career, going to the same college, etc.
She introduced herself as Sarah, and we spent the bulk of the wait and even on the train ride back to Jersey just flirting and talking to each other. I walked her to the parking lot where she parked her car and proceeded to exchange phone numbers with the intention of meeting up.
Anyways, the point I’m trying to make here is don’t over-analyze the opener. You can literally use anything, granted it’s congruent with your situation. Sometimes the simplest things can bring out the best results.
This is the second type of opener, which is also a little indirect and subtle, but just as effective as the functional opener. The observational opener is simply making an observation about the surrounding environment, her, or whatever the specific situation might be.
To clarify this with an example, I was walking through Washington Square Park the other day and noticed a huge congregation of people getting in a circle to watch these two guys. I saw this really pretty girl standing by the edge of the crowd and decided to position myself right by her so I could talk to her.
As I pretended to be curious about what was going on, I turned to her and asked, “Hey, do you have any idea what’s going on here, is this a fight?” She started laughing and said, “I wish, I’m trying to figure it out too, they might be getting ready to dance.”
Seeing that she looked really fashionable, I then followed up by making an observation about her. “Wow, I really just love your style, you must be a really creative person or work in some kind of fashion?” Her eyes lit up and she ended up telling me about her dream to become a fashion designer.
To make a long story short, the conversation stuck, we continue talking for the next half hour to an hour, and ended up grabbing some iced coffee from the nearest coffee shop down the block.
As I’ve said before, you can literally turn any situation into an opener. An opener is merely an ice breaker, and by coming under the radar, you come off as non-threatening and sociable. Just remember to be flirty, playful, and touch so you don’t end up getting friend zoned and sub-communicate that you’re interested in her.
This is something we teach in our live classes and is something that I utilize when I’m dealing with groups. The opinion opener is ideally used in bars where you can still hear your own voice, lounges, and networking events with large groups of people. We have a step-by-step structure with a backstory that follows it to provide context to a group situation when the conversation goes stale.
The way it works is simply asking the girl or group of girls with the girl you’re interested in their opinion on something. It could be pretty much anything (just avoid politics and religion). In general, to keep it more organic, I recommend picking topics that you’re genuinely interested in, or broad topics ranging from pop culture, dating and relationships, traveling, fashion, or hobbies.
For example, you could ask a girl or a group of girls their expert opinion on something like, “Hey guys, what do you think are the most attractive traits a guy must have if you were going to date him?” The point is, the question should always be positive with a funny twist if you really want to hook it.
The direct opener is simply directly laying out your intentions by introducing yourself and telling her that you wanted to meet her because you thought that she was cute, sexy, or beautiful.
I’m providing it here as another tool for your toolbox, and something you can utilize when you can’t use the other three types of openers, depending on your specific circumstances such as a time constraint.
But I personally don’t recommend that you utilize this approach regularly. As I mentioned earlier, while it may screen out only for girls who will say “yes” to you, in the long run you’re cutting out a large percentage of girls who are in the “maybe zone.”
Girls don’t want to feel pressured to make a yes or no decision about a guy right away or be put in an awkward position. I learned this the hard way, and at one point I was really adamant that this approach was the only way to convey your attraction to a girl.
While it did kill my approach anxiety and quickly build up my confidence because it made me develop a high tolerance to getting rejected, it didn’t do me any favors with developing social awareness, emotional intelligence, actually getting a date with a girl, or not getting a flaky phone number.
The analogy I often like to use is that the direct approach is like pulling a slot machine at a casino. It requires little to no thinking and is just pure chance. Dating in general is a numbers game, but over time with a little more experience, you develop your instincts and skills to ensure a higher percentage of success.
The direct opener is the easiest opener. But the problem lies in the fact that it isn’t efficient and will result in a higher rejection rate from girls who might have said yes to you if you didn’t lay out all your intentions upfront and put her in a situation where she feels pressured to make a yes or no decision right away.
That doesn’t mean I’m anti-direct, as I will tell you I’ve used this in situations where I was at a disadvantage and just wanted to go for the touchdown since I had nothing else to lose. One situation where I’d recommend using this is when you and her are pressed for time and you only have a short window to make an impression.
For example, I was at a bar and I saw this stunning girl who had dirty blonde hair. I wanted to talk to her but I had to leave the bar quickly as it was one of my best friends’ birthdays and we were out for a bar crawl. She was with a guy and I just had this hunch that she was on a date.
When the guy went to the bathroom, I made a little small talk with her and asked her if she was on a date. She told me yes, and based on her expression, she seemed disinterested in the guy that she was on the date with.
I said that I had to bounce quickly because of my friend’s birthday, and proceeded to tell her that I thought she was stunning, that I wanted to meet her, and wanted to take her out for some coffee the following day since she was on a date and that I had to get back to my friend’s party.
She giggled, smiled, and punched her number in my phone while calling her phone from my phone to ensure she got my contact info. I gave her a hug before her date came back and to make a long story short, we ended up hanging out the following day. But keep in mind that this situation won’t happen often. I would say it was pure luck on my part.
Another good situation to utilize a direct opener is when you know a girl is already attracted to you. You’ll know if she’s attracted to you once you’ve developed the reference experience. Pay attention to her non-verbal communication from the way she looks at you, if she’s checking you out, or is making an active effort to move closer and get into your line of vision so you can talk to her.
How do you know a girl is attracted to you? Refer to our article which describes seven signals she wants you to talk to her.
So there you have it, the four types of openers you can use to make every conversation stick. If you’re having trouble transitioning into conversations with a girl from an opener, or frequently run out of things to talk about, please take a look at our article on questions to ask a girl.
‘Til Next Time,
Hi, I'm Rob and welcome to our website!
In the last decade I've been coaching men (and women) in the art of connecting and finding love. I can tell you I've been referred to as "an asshole with a heart".
Just like other men who've been trying to figure out and understand the dating game, I used to be socially awkward. I'm a former Dating Mastery Program alumni and CofC apprentice with a decade worth of experience under my belt as a student, coach, and lifestyle mentor. My background is in applied psychology and I utilize a combination academic theory, research, and practical application towards our coaching.
I'm not a creepy pickup artist. I'm a normal guy that's competent, confident, and comfortable with women. My job is simple and that's to understand, nurture, support, motivate, and help you achieve and possibly realize the best version of yourself so you can authentically express yourself, connect with women (or men), and help you achieve whatever your dating goals may be in the most holistic, comprehensive, and practical manner.
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