How to Start a Conversation with Someone You’re Interested In

A woman who learned how to start a conversation with someone, chatting with a man she’s attracted to outside.

If you’re trying to express interest in someone, learning how to start a conversation is the first step. It can be daunting, sure, but there’s no way around it. If you want to see if you have chemistry with someone, you start by talking to them. Here are some tips to get you started.

1. Build your self-confidence.
The number one factor affecting your ability to start a conversation with a stranger is having confidence in yourself. Self-confidence is important, because it communicates a strong belief in yourself and your ability to deal with what life has to throw at you. People take cues on how to treat you based on how you carry yourself. If you’re self-confident, people will respect you. Of course, confidence doesn’t come easily to everyone.

If you need to build up your confidence, start by joining a sports team, signing up for a trivia league, or picking up a new hobby that’s more social like a painting or guitar classes. If you’re thinking this has nothing to do with your ability to make conversation, it does. By putting yourself in situations where it’s easier to talk to new people, you’re giving yourself an opportunity to practice your conversations skills in safe, low-pressure environments.

2. Develop conversational confidence.
Having confidence in yourself is one thing, but you need conversational confidence as well. Maybe you have friends and family you chat with regularly, but you’re shy around new people. Shyness comes from your perception that what you’re feeling or have to say is somehow inadequate and won’t be received well. The best way to get over this feeling is simple practice. Social skills are like a muscle, so make sure to keep them in good shape.

A good way to build up your conversational confidence is to chat up strangers that work in service and hospitality. Make conversation with baristas, the cashier at the grocery store, or the ticket teller at your local movie theater—they’re paid to be nice to you, so there’s nothing to be afraid of. These microinteractions will train you to pick up on natural rhythms of conversation and nonverbal cues. Set a goal for how many of these interactions you want to have per day, even if you start at one. It will build your conversational instincts and help you get over that initial feeling of inadequacy.

3. Understand and control your nerves.
OK, the next step is to talk to someone you’re attracted to. When you see someone you want to chat with, do a quick body check. If your heart’s racing, take a couple deep breaths in through your nose and out through your mouth to calm yourself down.

There are two main reasons people get nervous starting a conversation with someone they’re attracted to: fear of rejection and mismanaged expectations.

Fear of rejection often stems from an irrational fear that the person you’re approaching will humiliate you for even attempting to hit on them. The truth is most people who refuse your offer to start a conversation  will be very polite about it. More importantly, don’t make a rejection mean anything other than that they weren’t interested. Some people have a tendency to equate their self-worth with their romantic success or their ability to start these conversations. It doesn’t work that way. Rejection is part of dating and everyone goes through it. Let it go and move on.

Mismanaged expectations usually come with inexperience. Inexperienced flirters usually expect every conversation with a crush to be a hypersexual exchange of innuendo and batted eyelashes. While this does happen, it’s usually the exception not the rule. Initial contact conversations are usually normal conversations. They’re a way for two strangers to chat and decide if a conversation is worth continuing. That’s it. The romance comes later.

4. Be natural.
At this point you may have prepared a bunch of canned lines ready to start your conversation. Stop. Don’t use them. You don’t need openers or corny pickup lines to start a conversation. If you’re chatting with a friend, you don’t rehearse things to say to them—you just talk. That’s the energy you want to channel. Tap into the improvisational element of conversation. People can feel when it’s genuine and when it’s not. The best opening you can start with is something specific to the moment. If you’re in a bookstore, ask about the books they’re looking at. If you’re at a volunteering even, ask how long they’ve been doing volunteer work. If you don’t know how to start, just say “Hi, my name is… How’s it going?”

Just chat and be natural, like this person is your friend, because that’s the goal isn’t it? Don’t focus on the physical attraction, but on the content of what the other person is saying. Ask questions. Get their opinions. Share an appropriate amount in response. Get a feel for whether you’re interested in keeping the conversation going. I can’t stress this enough: confidence is the key to letting go of your self-consciousness and it will take you farther in your love life than any other advice.

5. Pay attention to body language.
Now that you’re talking, pay attention to body language. Usually the conversation will take some time to warm up. That’s normal. If the person seems talkative, they’ll turn to face you and make good eye contact. Usually it will take a few minutes to get here.

But know when to exit. If you’ve been chatting for a few minutes and they’re still half turned away like they’re ready to leave or just giving you short responses, it’s time to call it quits. Respect their choice and make your exit. On the other hand, if the conversation is really gaining some traction keep chatting until things slow down. When they do, offer to exchange phone numbers and suggest meeting up in the future.

Learning how to start a conversation, especially with a stranger, is hard for anyone. So if you hit some bumps in the road, don’t worry. Missteps and mistakes are a natural part of getting to know people and learning what does and doesn’t work for you is an important part of dating. With more knowledge, a little guts, and a lot of practice you may be surprised by how strong a conversation starter you can be.

Alex Bocknek

Alex Bocknek is the senior editor of The Date Mix and works at Zoosk, the online dating service. He’s also a recovering music critic and an aspiring fiction writer (probably lost) on the way to an independent bookstore near you. He can be found occasionally musing about politics, philosophy, and love in the modern world.

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