A lot of men think dating gets easier when they find the perfect line. It usually gets easier when they stop waiting for the perfect moment and speak while the chance is still in front of them.
Start the conversation before you feel ready
You see a woman you want to meet at a coffee shop. You look at your phone, fix your shirt, and wait for a better time. She finishes her drink, puts on her coat, and walks out.
You didn't need a better line. You needed to walk over and speak.
Keep your first line tied to the place. Say, “You look like you know what to order here. What’s good?”
If she smiles and answers, say, “Good. I’m getting that next time. I’m Mark, by the way.”
You don't need to perform. You need to make the first few seconds easy for both of you. A simple question gives her something to answer. Your name makes the exchange feel like two people meeting instead of a stranger asking for attention.
If she gives short answers, keeps looking at her phone, or turns her body away, leave with a smile. Say, “Have a good one.” Then walk away.
A man who can start a conversation can also end one without making the woman carry the whole exchange.
Give her something real to respond to
Many men ask questions that sound like job interviews.
“What do you do?”
“Where are you from?”
“What do you do for fun?”
One question is fine. Five in a row makes you sound like you're filling out a form.
Use what she says. If she tells you she works with children, don't fire off another random question. Say, “You must have a lot of patience. I lasted one afternoon helping my nephew with homework.”
Now she has something about you. She can ask about your nephew, laugh at the story, or tell you about a difficult child at work.
A good conversation moves back and forth. You ask about her, then share a small piece of your own life.
For example:
“You come here often?”
“I come when I need coffee and quiet.”
“Same. I work from home, so my apartment gets too quiet. I start talking to the dog.”
That line gives her a picture. She can ask about the dog, talk about her own pet, or tease you about talking to yourself.
Don't tell your whole life story. Give her one clear detail, then let her choose where to take the conversation.
Show interest without asking for approval
A woman should know you're interested. If you hide your interest, she may think you want friendship or nothing at all.
You can say, “I like your style. You look sharp.”
Then keep talking. Don't stand there waiting for her to praise you or return the compliment.
You can also say, “I’ve enjoyed talking with you. Let’s get coffee another time.”
That sentence is clear. It doesn't ask her to decide if you're worthy. It tells her what you want and gives her room to answer.
If she says yes, take out your phone and say, “Put your number in here.”
If she says she’s busy, ask once, “What day works better?”
If she gives a real answer, set a plan. If she stays vague, smile and say, “No problem. Have a good day.”
Don't bargain with her. Don't ask why she doesn't want to meet. Don't send five texts to change her mind. Interest has to go both ways.
Make plans that are easy to accept
“Let’s hang out sometime” is weak because neither of you knows what it means.
Pick a place and a time. A short coffee or a drink works well because it gives both of you an easy way to leave after an hour.
Say, “There’s a small coffee place near the park. Come with me for a drink at 6.”
Now she can say yes, suggest another time, or say no.
When she agrees, don't keep texting all day. Send the details:
“Good. Meet me outside the cafe at 6. I’ll be wearing a gray jacket.”
On the date, don't turn the meeting into a test. You don't need to prove that you have an exciting life every minute. Talk about places you like, food you hate, trips you want to take, and the strange things that happen at work.
If she tells a story, listen. Ask one question about it. Then share your own story.
A guy I coached used to plan dates that lasted three hours. He hoped more time would make women like him. Most of the women stopped replying after those dates. He changed one thing. He started asking for a short coffee instead. He talked less, asked better questions, and ended the date while the conversation still felt good.
The women he met began agreeing to see him again.
Handle silence like a grown man
Sometimes she won't reply. Sometimes she will cancel. Sometimes she will enjoy the date but still say she doesn't want another one.
That hurts, but chasing her will not change the answer.
Send one clear message if you need to confirm plans:
“Are we still on for 6?”
If she doesn't answer, don't send three more messages. Make another plan with your own evening.
If she cancels and offers another time, set it. If she cancels without offering another time, say, “No worries. Take care.”
You don't need to act cold. You also don't need to write a speech about how much effort you made.
Your job is simple. Start the conversation. Share real details. Make a clear plan. Watch whether she meets you halfway. Then keep your standards when she doesn't.
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.
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- 02How to Make Dating Easier by Changing Simple Habits6m
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- 0520 Years Later... Why I’m Still a Dating Coach8m
- 06Walk and Carry Yourself So She Notices Before You Speak6m