5 Conversation Starters That Actually Work

You’ve done it: you’ve successfully matched with someone! But with so much pressure to say the right thing (and so much potential to say the wrong thing), it can be hard to make any move at all. Small talk — even the classic “tell me about yourself” — is way more difficult than it should be, and often turns into a robotic, interview-like conversation. To combat this, here are five simple and effective exercises that will actually capture someone’s attention and spark authentic, engaging conversation that lasts longer than one word.

1. Small talk, revamped

Small talk doesn’t have to be shallow or boring like many people think. When done efficiently, it can express a genuine interest in getting to know someone, and even inspire meaningful conversation! Instead of asking questions that give one-word responses, rephrase them for open-ended answers that encourage more thought and explanation. Three examples are:

How was your day? → What was the high and low of, and who was the hero of, your day?

Where are you from? → Where is your favorite place in your hometown? What was the most interesting part of your childhood?

What do you do? → What’s your current job like vs. your dream job?

2. What are you most proud of and/or passionate about?

Honestly, most people secretly enjoy being asked to talk about themselves, as it gives us an opportunity to discuss our accomplishments and interests without coming off as conceited. In general, listeners will appreciate when you express interest in something you are passionate about or proud of, and will match your enthusiasm.

3. Embarrassing stories battle

Asking for embarrassing moments may seem a bit extreme to begin with, but it can actually be a really effective and engaging icebreaker. People will naturally start with a less embarrassing memory, but as the conversation goes back and forth and the stories get more and more embarrassing, you are guaranteed a fun, laugh-worthy time. Plus, everyone can relate to a cringe-worthy moment, so this idea can help quickly connect two people.

4. What are some things on your bucket list?

Their response also allows you to quickly get to know them, which is a win-win situation: if nothing on their bucket list matches yours, you can still ask them to explain answers further, but if something does match one of yours, then you can bond over the similarity. Listening to people list their goals shows that they are attempting to live life to its fullest, and it is genuinely interesting to hear each person’s own bucket list contents.

5. What is the most different or “unlike yourself” thing you’ve ever done?

This is a variant of the tiresome “tell me about yourself,” as learning about who someone is not can tell you a lot about who someone is. Whether the response is a funny, one-time event or a longer period of self-discovery, this is an awesome exercise to encourage more thought, and a personal — yet easy — look into someone’s personality.