When you approach a woman in person, give small talk about a minute or two, then change the kind of thing you are talking about. Move from facts like where she is from and what she does to opinions, reactions and a little playfulness. At the same time, make it clear the conversation is between a man and a woman, not two colleagues. When the tone shifts from information to energy, small talk turns into interest.
What small talk is for
Small talk is not a mistake. "What brings you here?" and "How long have you lived in the city?" tell her you are friendly and harmless. They lower her guard.
The problem is staying there. A conversation made only of questions and facts feels like a form being filled in. Neither of you is learning anything about the other as people. After a few minutes she is polite, and then she leaves.
Treat small talk as a doorway, not a room. The first minute is there to make her comfortable, and the second is there to make her curious.
Notice the signal to move on
You do not need a timer. Move when the facts have run out, or when you notice any of these.
- Her answers have turned short and polite.
- You have asked three questions in a row.
- You feel the urge to ask yet another one.
- She has relaxed but is waiting for you to lead.
a dating coach stresses that the man has to carry the early part of a conversation, since she did not start it. That includes steering it somewhere more interesting.
Switch from facts to feelings
Ask about what she likes, not just what she does. "What do you do?" gets a job title. "Do you actually enjoy it, or is it just paying the bills?" gets a reaction.
Questions that bring out opinion and mood work best.
- "What is the best part of your week so far?"
- "What are you weirdly passionate about?"
- "If you could skip one thing in your normal week, what would it be?"
Then react to what she says. If she tells you she hates mornings, do not just nod. "So you are a night person who is forced to function. Respect." Your reaction is what turns an answer into a conversation.
Share something of yourself
Real interest goes both ways. If you only ask questions, you are an interviewer, and she is the interviewee.
Give a short, honest opinion or a small story, then hand the floor back. "I used to hate running, and now I get oddly competitive about it. What is yours?" invites her in. It also shows who you are, which is what she is trying to find out.
Keep these stories short. Thirty seconds is plenty.
Make it man to woman
a dating coach's idea of premise is useful here: the shared understanding of what is going on. If the premise is a friendly chat between two people, nothing will happen. You want her to see that this is a man and a woman who might be interested in each other.
You do this lightly. A playful tease, a specific compliment, or a bit of flirtatious banter does it. "You seem like trouble, but I like it" is man to woman. "Where do you work?" is not.
Tease only as much as she can handle. If she laughs and teases back, you are in. If she goes quiet, ease off and return to friendly.
Keep the energy up
When the conversation reaches real interest, you will notice it. She gives longer answers, she laughs, she asks you things, and she has stopped glancing around.
Stay there for a few minutes and enjoy it. Do not rush to the number the instant she smiles, and do not drag it out until the energy fades. Then, when it feels natural, suggest the next step: a number, an Instagram, or a coffee now. Interest that is never acted on fades.
If she stays at the surface
Some women stay in small talk no matter what you do. She may be shy, busy, or simply not interested. Try once with a more personal question and a lighter tone. If she still answers in the same flat way, thank her and leave.
Learn it live
This transition is easy to explain and hard to do, because it depends on timing, tone and her reaction in the moment.
That is why a Cold Approach Bootcamp is taught in the field, in Miami and New York, with live coaching on every approach and feedback after every set. Keeping the conversation going without turning it into an interview is part of the first of the four parts covered every training day. Attraction and delivery, including genuine interest and flirting, is the second.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.




















