A good conversation starter notices something real about the moment you are both in and hands her one easy thing to answer. "That is a bold choice of drink, what is the story?" beats "hi, how are you?" every time. Pick something unusual you can see or hear, say it in a friendly tone, and ask a narrow question. Then listen and say something about yourself, so it turns into a conversation and not an interview.
Why most starters fall flat
"How is your day?" and "what do you do?" are common, so she has a standard answer ready, and it is a dull one. Both questions are also huge. She has to decide how much to say and what you want to hear.
coach describes boring conversation as a mix of three problems: asking lame questions, running out of things to say and drifting onto dry topics. The fix is to stop collecting facts and start playing with what is in front of you.
A narrow question has a small, obvious answer. "Which of these two bands is better?" takes two seconds, and she will usually add a reason.
The best starter is something you noticed
My favorite type is the observational opener. Look for something a little unusual about the person or the place, make a light, exaggerated comment about it, and let her react.
If she is wearing a bright yellow coat: "I could see you from across the room. Is that coat a safety feature?" If she is reading a thick book at a bar: "That book looks like it has opinions. Is it winning?"
The detail needs to be unusual, because "nice jeans" gives her nothing to play with. Your comment can be a little silly. If it is warm, she will smile, and then the conversation starts.
Starters for common places
At a bar or party, use the setting. "What is the best thing you have heard here tonight?" or "Settle something for my friends and me: is it too early for a second drink?" gives her an easy way in.
At the gym, keep it brief and respect her workout. A short, friendly line between sets works better than a long chat: "That is a serious routine. How long have you been doing it?" If she gives a short answer or puts headphones back in, say "nice talking to you" and move on.
At school or in class, use the shared experience. "Did you understand the reading, or is it just me?" is easy to answer and starts a normal chat. Keep it casual and do not hover.
Online, by message, pick something from her page and ask one narrow question about it: "Which trail was that photo from?" Skip "hey" and "how are you."
For a shy girl
Make it easy. Ask a small question, smile and give her time to answer without rushing. Offer an either-or: "Coffee person or tea person?" Share a bit about yourself so she does not feel she is being quizzed.
Do not fill every silence. A shy woman often warms up when she is not under pressure, and she will take a step toward you if you let her.
For a girl you already like
Do not turn on a special voice. Talk the way you would to a friend, and use what you know. If she mentioned a trip, ask how it went. If she is always carrying a certain mug, tease her about it.
Do not open with a big confession. A light, specific question will do more than a heavy declaration.
If you are talking to your girlfriend
The same idea works. Skip "how was your day?" and ask about a specific moment: "What was the funniest thing that happened today?" or "What was the best part of your week?" She will give a real answer.
Keep it going
After your first line, listen for what she gives you and follow it. My trick for dead air is to start a sentence with "yes, and" and finish it however you like, because starting to talk gets your brain working for you instead of against you.
Say one thing about yourself for every question you ask. Let her end the conversation if she wants to, and take it well.
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.