How to Start a Conversation With Someone You Like

Figuring out how to start a conversation with someone you like can feel harder than any job interview. With a stranger, there is nothing to lose. With someone you like, suddenly every word feels like it matters. Here is the good news: the first line is not that important. What matters is that you say something, and then that you listen. Let's make the first step easy, both in person and by text.

Lower the stakes first

You are not trying to win them over in one conversation. You are trying to have one nice exchange. That is it. If it goes well, you have another one later. Attraction usually builds over several small moments, not one perfect speech.

So give yourself a tiny goal: "I am going to say hi and ask one question." You can do that.

How to start a conversation with someone you like in person

In person, you have the huge advantage of a shared moment. Use it. A simple formula:

Notice something in the moment. The music, the line, the event, the thing they are holding.
Say it out loud, simply. "This song is a throwback." "Is the coffee here as good as everyone says?"
Ask an open question. One they cannot answer with a yes or no. "What are you working on?" "How do you know everyone here?"
Introduce yourself. After a minute or two of talking: "I'm Jordan, by the way."

Or go straight to a genuine compliment about something they chose: their jacket, their playlist, the way they handled a rude customer. A specific, sincere compliment is one of the best openers there is, because people rarely hear one. Dawn teaches this at the start of every speed dating night; read about the method on our learn how to date page.

Openers that work in common situations

At class or the gym: "Did you understand that last part? Because I definitely did not."
At a party: "How do you know the host? I want the embarrassing stories."
At work or school: "You always seem to know the best lunch spots. Where should I go today?"
At a coffee shop: "What did you order? I am stuck between two things."
At an event: "Have you been to one of these before? What should I expect?"

How to start a conversation by text

Texting someone you like gives you time to think, which is great, and time to overthink, which is not. Keep it light and specific.

Reference something real. "I tried that taco place you mentioned. You were right." That shows you listened.
Ask one question, not five. Give them an easy thing to answer.
Skip "hey" and "wyd." They put all the work on the other person.
Match their energy. If they write long messages, you can too. If they keep it short, so do you.
Do not double text all day. One message, then let them answer.

A few easy first texts: "Okay, settle this: best pizza in town?" or "I saw a dog that looked exactly like yours today and thought of you." or "That thing you said about road trips got me thinking. Where would you go if you could leave tomorrow?"

Keep it going after hello

Once the conversation starts, your job is to be interested, not interesting. Follow up on what they say. Share a little about yourself so it does not feel like an interview. Laugh at the funny parts. When they light up about something, ask one more question about it.

And watch for signs of interest. People who are into talking with you usually ask questions back, make eye contact, smile, turn toward you and keep the conversation going. Short answers, glancing away and looking at their phone usually mean they want to wrap up. Respect that. A friendly "Good talking to you" leaves the door open for another day.

When to ask them out

If the conversation is going well, do not wait for a perfect moment. Ask while things are good. Keep it specific and easy:

"I am really enjoying this. Want to keep it going over coffee Saturday?"
"There is a trivia night Thursday. Want to be on my team?"
"Can I get your number? I would love to call you this week."

If they say yes, follow through, and call rather than letting it fade into endless texting. If they say no, smile and say, "No problem, it was great talking to you." Handling a no with kindness is a skill, and it is very attractive.

Practice makes it easy

The more conversations you start, the less scary each one feels. Chat with the barista, the person next to you in line, your neighbor. You are training your brain that talking to people is safe and fun.

Want a whole night of practice? Now or Never is our speed dating in Las Vegas for everyone 21 and over. You get the lesson first, then short timed dates where the hard part, starting the conversation, is built in. New dates are coming soon, so register free to hear first. For daily practice noticing the good in people, try Compliments for Change.

Your turn

Who is someone you like that you could start a real conversation with this week, and which opener will you try?

Keep the love going

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This article first appeared on Now or Never Speed Dating, part of The Love Effect family of sites.