Ask open-ended questions.
Open-ended questions require a longer answer than just “yes” or “no.” Try to tweak your questions so he’s more motivated to write out something in-depth, which will get the conversation going. Pretend to ask yourself the question first—if you can answer the question within a word or 2, it probably won’t keep your conversation going for very long. For instance, “What are your plans for the weekend?” is a better question than “Do you have anything exciting planned over the weekend?” If you’re feeling adventurous, ask a fun question, like “What’s the weirdest corner of the internet you’ve stumbled across?” or “If you had a budget of 1 million dollars for a party, how would you spend it?”
Offer follow-up questions.
Follow-up questions revert the conversation in his direction. These questions don’t have to be over-the-top. A simple “Then what?” or “How so?” can inspire him to keep talking. You can even turn your follow-up question into a compliment, saying something like “That’s so cool! Could you tell me more?” or “Please go on! This is so interesting.” If you’re worried about sounding too aggressive, hedge your question with a friendly statement, like “If you don’t mind me asking” or “If you’re comfortable.” A great way to follow up is repeating his last statement like a question. If he said, “I’m heading upstate for the weekend,” you might say, “So, you’re going away for the weekend?” This might inspire him to keep talking about himself. Follow-up questions are a great way to stay engaged without turning the chat into an interrogation.
Talk about your favorite topics.
It’s easier to navigate a conversation that’s in familiar territory. Look for ways to connect your conversation to something you’re really knowledgeable or familiar with. If the conversation starts to falter, lean on some of these topics for support. You might say, “Speaking of video games, I found a really cool site that lets you sign up for alerts on your favorite games” or “That reminds of something funny I overheard in class today.”
Chat about his interests.
See what books, movies, and other fun things he’s into. Depending on his answer, you might be able to compare notes on some of your favorite titles or jot down some recommendations for yourself. It can be a shot in the dark, but this conversation topic might lead to a pretty interesting chat. This topic can sound pretty abrupt, and may not be the best way to start a conversation. However, it’s a great way to keep your chat going! You might ask, “Read any good books lately?” or “If you were stuck on a desert island, what 3 movies would you bring with you and why?”
Discuss what you have in common.
Sports, hobbies, and other popular topics are a great way to keep your conversation going. Think about something you both like, even if it’s pretty small. Chatting about a tough class, a mutual friend, or a similar job could help reinvigorate your conversation. For instance, you might talk about a local sports team, or compare notes about a frustrating teacher at school.
Compliment him.
Compliments help guide your conversation through any awkward silence. Instead of pressuring yourself to think of something fun and creative, put the focus on him. A kind comment or compliment can help reinvigorate your conversation! You might say, “I was really impressed how you finished that math test so quickly!” or, “I thought no one could pull off wearing a football jersey, but you really proved me wrong.”
Blurt whatever is on your mind.
Don’t be afraid to change the subject. Blurting your thoughts may seem a little strange, but it’s a great way to keep your conversation going. Most people don’t mind a random topic change and are happy to follow whatever direction the conversation takes. You might start your statement with “This is a little random, but…” or “I was just thinking…”
Reminisce about your childhood.
Childhood nostalgia is a great way to break the ice. Chat with him about some of his favorite childhood memories, or some hilarious childhood memories. Then, keep the conversation going by sharing your own tales. Everyone has an interesting childhood story to tell, so this is a great way to get the ball rolling. You might say, “My mom just dug up some old photo albums yesterday. Do you have any Kodak moments from your childhood?”
Transition smoothly between topics.
Questions and word associations are great ways to switch topics. If the guy asks you a question, guide the conversation in a different direction with your answer. If he’s not feeling super chatty, build off a word or detail from the last thing he said. Word association is a simple, clever way to switch topics without seeming too random. If he asks “how are you,” you could talk about your weekend or a fun hobby that you enjoy. If he mentions his car, you might say, “I love long car rides, but for me, nothing can beat an early morning hike. Do you like any outdoor activities?”
Try a different way to communicate.
See if he’d like to call or video chat. Sometimes, a text conversation just doesn’t cut it. Ask if he’d like to call or video chat—worst-case scenario, he isn’t interested. Best case scenario, you both have a fun chat together and become even closer! You could say, “I have a little free time right now. Want to video chat for a few minutes?”
Don’t dominate the conversation.
Frequent messages and being the only one talking can make you seem a bit desperate. It’s totally understandable if you want to keep things going, especially if your chat was off to a good start. Just remember—your time is just as valuable as his. If he doesn’t seem that interested in chatting with you, he probably isn’t worth your time and energy. For example, if you’re texting him, refrain from sending more than 2 messages in a row.
Avoid talking about your relationship status.
Complaining about being single can turn him off. While it’s perfectly valid and understandable to feel frustrated about your relationship status, you’re much better off venting your feelings to a trusted friend or loved one instead of the guy you like.
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