How to Start a Conversation: With Your Crush, a Stranger, or Friend

By Angela Saulsbery, M.A.
Reviewed by Tchiki Davis, M.A., Ph.D.

Do you want to reach out, but aren’t sure how? Learn how to connect with acquaintances, crushes, and new friends–and even how to start tough conversations.

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Maybe, like me, you’ve made a New Year’s Resolution to be more social—to make more friends, go to more events, or even find a new partner. But, when you get the chance to meet new people, you’re not sure what to say. Maybe you stumble through an awkward opening, go quiet, or avoid new people altogether.

It’s typical to feel anxious about meeting new people and putting yourself out there. Knowing some tried-and-true conversation starters can boost your confidence: Even though you can’t control everything about how other people respond to you, you can definitely plan ahead to smooth the way to a great conversation.

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How to Start a Conversation With Your Crush

What is your relationship to your crush? Are they a friend, a friend of a friend, an acquaintance, or someone you gaze at from afar every morning at your favorite coffee shop? Your current relationship to your crush, as well as both of your personalities, will determine the best ways to approach them. In my experience, it’s best to be direct about your interest while respecting your crush’s boundaries and freedom to turn you down.

Assuming that you’re not already friends with your crush and that you’d like to get to know them better, light conversation or “small talk” is a good way to build rapport. If your crush is a friend of a friend, and your mutual friend is trustworthy, you can let them know that you’d appreciate more opportunities to hang out as a group. These conversations will probably give you a better idea of who your crush is, whether they’re actually someone you’d like to date, and what shared interests the two of you have. For example, if you both love a musician that your other friend doesn’t love, you can say, “Hey, Tamara Shift is playing live here next month. Do you want to go?”

If the crush is an acquaintance, strike up a conversation based on your shared setting. For example, I met one of my closest college friends at an internship. Our early conversations revolved around the quirky goings-on at the office. These chats naturally progressed to lunches in the neighborhood where we worked. After a few weeks, she invited me to a party she was throwing the next weekend. You can build a relationship with a crush in the same way.

If the crush is a stranger, and you’re looking for a relationship, I don’t recommend mooning over them from across a crowded café for the next several months. As long as the stranger looks age-appropriate and doesn’t seem desperate to be left alone, you can probably find a good moment to exchange a few words with them. For example, if you’re in line together at the café, you can say something like, “Have you ever tried the pastries here? Is the blueberry muffin good?” Your opening line doesn’t need to come off as staggeringly brilliant—the point is not to impress; it’s to offer a moment of connection and see whether the other person is open to it.

How to Start a Conversation With a Girl

First, if you see a woman in public wearing headphones and reading a book, she probably isn’t open to conversation. Little is more annoying than having to pause your podcast and take out an earbud to figure out what some stranger on the subway is saying to you. I’d rather read another page of my book than brace myself for sexual harassment while scrambling for a response that won’t come across as insulting or encouraging. It’s not fun.

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How to Start a Conversation With a Stranger

Research shows that, although we often prefer to keep to ourselves, people report that they experience grater positive emotions after greeting, thanking, or expressing good wishes to their shuttle driver during a commute (Gunaydin et al., 2021). Indeed, even small things like striking up a casual conversation with the grocery store clerk as been shown to increase feelings of well-being (Martela & Ryan, 2016).

Video: Start a Conversation with Anyone with These Killer Conversation Starters

How to Start a Conversation With an Old Friend

Do you have an old friend whom you miss and keep planning to call–then next thing you know, 6 months have gone by? Don’t sweat it–almost everyone is busy, and it’s likely your friend will be excited and happy to hear from you. When I’ve fallen out of touch with a friend, I text, “Hey, how are you? Do you have time to catch up in the next couple of weeks?” I’ve also been known to simply pick up the phone and call–although this extreme extrovert move may not work for everyone. My friends and I also like to exchange postcards occasionally–it’s rare and exciting to receive mail that isn’t junk, and I always feel special finding a card or postcard among my assorted grocery store flyers and credit card offers. A cute postcard often turns into a multi-hour video chat.

How to Start a Conversation After a Fight

If you’ve recently fought with someone and are looking to resolve the conflict, an in-person conversation may prevent misunderstandings and restore warmth and connection. If meeting in person isn’t possible, a phone call or video chat at least lets you see the other person’s facial expressions or hear their tone of voice. When starting a conversation after a fight, I recommend being direct, clear, non-blaming, and respectful of both the other person and yourself (for example, you don’t need to take all the blame if the other person hurt you and contributed to the conflict as well).

When a friend recently insulted me during a tense conversation, I didn’t address her cruel words in the moment. When I next saw her a few days later, I eased into the conversation with a minute of small talk, then said, “I want you to know that I was hurt by what you said to me the other day, and it’s not okay for you to talk to me like that. It doesn’t have to be now, but I’d like to talk more about it at some point, because it really was not okay.”

I waited until we’d calmed down but didn’t procrastinate and pretend nothing was wrong while I simmered with resentment. I expressed my hurt feelings using an “I statement” and drew a boundary without matching her aggression. And I gave her space to meet me halfway instead of demanding that she drop everything immediately for a possibly long, intense conversation. I couldn’t control her response, but I didn’t want to or need to—I’d done what I could do and was willing to do to repair the friendship.

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How to Start a Hard Conversation

Similarly to conversations after a fight, I suggest starting a hard conversation when both you and the other person feel calm. I also suggest being direct, non-blaming, as clear as possible, and respectful of both your own and the other’s feelings and needs. It can also help to broach the challenging subject during a shared activity, such as a walk. Many people feel more comfortable discussing emotional subjects when they’re walking or working with their hands (as opposed to sitting across from another person who expects consistent eye contact).

For example, after a couple of particularly busy weeks, I wanted more time with my partner. As we drove to the grocery store, I said, “I missed you this week. I’d like to spend a bit more time with you.” Although this vulnerability felt a little uncomfortable, asking for what I wanted worked: He immediately suggested an additional day that week for us to hang out.

How to Start a Conversation Examples

As an extrovert, I enjoy small talk and striking up conversations with interesting people–strangers, acquaintances, new friends, and old friends. Below, I provide several examples of recent conversation starters that I’ve used, others have used to start conversations with me, or that I’ve seen friends use successfully.

“I love your hair!” – Most people appreciate a sincere, non-creepy compliment, especially if you’re complimenting something they put effort into. In this case, a stranger was complimenting my friend’s freshly-colored aqua blue hair.
“Can I pet your dog?” – How I broke the ice with a neighbor whose dog was sitting at my feet, staring up at me and wagging her tail. (His answer, delightfully, was, “It’s up to her.”)
“Do you work with ___?” – How I began my first conversation with a coworker whom I’d passed in the hallway several times since my first day.
“Do you want to catch up over the phone sometime this week?” – A frequent text from or to my long-distance friends.
“I was by [football stadium] the other day!” – Text to my brother, who loves professional sports.
“So…who are you people?” – A close long-distance friend of my partner and I had introduced us to someone she met at a workshop who lives in our city. Our new acquaintance started the conversation this way once she, her partner, my partner, and I were settled at a table with our coffees and snacks. I appreciated her bluntness, and it began an hours-long conversation that stretched into dinner at a second location.

How to Start a Conversation Over Text

Depending on the recipient of your text, starting a conversation can be as simple as asking, “How are you?” or sending a cute picture of your pet. I often start text conversations with my partner by sending a kiss emoji and asking, “How was your day? Did you make it to yoga?” Generally, people seem to appreciate a greeting, a question following up about something you recently spoke about, and/or an invitation to hang out. You can use your judgment as to what’s appropriate–for example, if you’ve texted an acquaintance twice and they haven’t responded, you might want to leave them alone.

How to Start a Conversation on a Dating App

The key to starting a conversation on a dating app is to prove that you read your match’s profile. Unless you are incredibly good-looking, sending a heart or a simple “hey” probably won’t get you an enthusiastic response—if you send one of these low-effort messages, you’re putting the onus on the person you’re supposedly interested in to start the conversation. Receiving a one-word message has rarely sparked my curiosity or given me a good feeling about the sender’s ability to hold up their end of a mutual, meaningful relationship (or even an entertaining few dates).

Instead, pique that person’s interest and give them something substantial to respond to. If you can make a (non-offensive) joke, it’s absolutely worth a try—you don’t know this person yet, so you have nothing to lose, and if you can make them laugh, they’ll probably feel positively toward you. Also, there are low stakes and very little pressure–you don’t need to marry this person; your goal can just be to find out whether they’re interesting enough and your conversation flows smoothly enough that you want to go for coffee with them. (And your goal for that coffee can be to see whether you want to go on a second date, and so on.)

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Final Thoughts on How to Start a Conversation

When striking up a conversation to connect socially, you can think back to what you have enjoyed or appreciated when others struck up conversations with you. Most people respond positively to friendliness, sincerity, respect for boundaries, humor, and appreciation. Also, dating and making friends can be a numbers game–if, for example, someone doesn’t reply to your dating site message, you can respectfully leave them alone—their silence doesn’t mean that no one will respond, and out of the many users of the app, someone probably will. Last, when building social skills, you can practice a growth mindset and treat each interaction as a mini experiment. With practice and reflection, I’m confident that you’ll find conversation starters that work for you!

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References

Gunaydin, G., Oztekin, H., Karabulut, D. H., & Salman-Engin, S. (2021). Minimal social interactions with strangers predict greater subjective well-being. Journal of Happiness Studies, 22, 1839-1853.
Martela, F., & Ryan, R. M. (2016). Prosocial behavior increases well-being and vitality even without contact with the beneficiary: Causal and behavioral evidence. Motivation and Emotion, 40(3), 351–357.