With Your Crush, a Stranger, or Friend

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.​

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).
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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.

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. 

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.) 

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!

• ​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.