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Swiping on dating apps can often feel like being in the romantic trenches. Even when you come across a hottie with a non-boring profile, you’re probably all too familiar with the struggle of coming up with a witty first message. You hope they see it and their interest is piqued, and then you wait…for a measly “haha” in response. Meh. But that doesn’t mean you’re out of luck just yet. Knowing how to keep a conversation going on an app, over text, in person, or through DMs is about putting your best foot forward, and more importantly, being confident enough to do so.
If you get a little nervous along the way, that’s okay too—no one is automatically just good at small talk. Like any skill, it takes practice. You just have to know what to ask and be willing to put yourself out there. Licensed clinical psychologist Dr. Morgan Anderson, attachment theory expert, relationship coach, and author of Love Magnet, says you deserve to ask questions that you actually want the answer to, and questions that give you the info you need to decide whether you actually want to meet them IRL. So don’t be afraid to get a little creative!
Need help getting started on how to keep a conversation going, or just want to brush up on some social skills to make sure your topics are fun and fresh? We tapped a few experts who shared key tips, whether you’re sending that first dating app message or getting to know each other on your first date.
1. Learn How to Ask a Seriously Good Question
“How long have you lived in the city?” is something you might want to know on a first date, but it’s a question that’s going to lead to a dead end, simple answer. Instead, try a more open-ended question that has a better likelihood of leading to a natural conversation.
Anderson loves questions like, “What are you most excited about right now?” This is a great way to learn what your date is passionate about and what lights them up. If you ask someone what their hobbies are, they might clam up or try to come up with something that sounds interesting or good enough as an answer. Asking what that person is excited about reveals their passions in a more natural way.
2. Avoid an Interrogation
When the questions you’re asking your love interest start to feel like the same ones you’d ask someone you’re interviewing for a job, take a step back. “If there are too many non-open-ended questions, it could feel like an interrogation, which could feel like a huge red flag,” explains Los Angeles-based licensed psychotherapist Adrine Davtyan, LCSW, owner of Serenity Therapy. After all, dating should be fun, and no one wants to feel like they’re interviewing for the role of partner. Instead, Davtyan recommends asking questions that start with words like “what,” “how,” “why,” and “tell me about…” Think: “Tell me about the last concert you went to,” or “What does an average weekend look like for you?”
3. Don't Make the Conversation All About You
Raise your hand if you’ve ever been on a date where the other person totally fails to ask you anything even remotely interesting about yourself. It’s a struggle that, unfortunately, many people face while talking to someone they’re still getting to know. And while it’s perfectly natural to be nervous and feel the need to oversell yourself to the person you’re talking to, it often has the opposite effect.
If you find yourself on a date where you're so nervous that all you can do is list off your achievements, as incredible as they are, remember that it’s a two-way street and they probably have tons of interesting info they want to share with you, too. Ask them questions about their friends, their work, their hobbies, or about what they’re looking for in a partner.
“When getting to know someone new, you want to make sure that you’re curious about who they are and what’s important to them,” says Anderson. “Instead of making assumptions about them, you'll improve the connection by asking lots of questions. For example, if I’m getting to know someone and we’re chatting over text, I’ll ask them questions that I genuinely want to know the answer to, like, ‘What was the best part of your day, and why?’"
4. Avoid Judgement
Another key aspect to staying curious is to avoid inserting judgment, which can halt a conversation faster than spilling your drink all over the table. “You may be into someone, yet disagree with a perspective they may have on a certain topic,” says Davtyan. “Exploring why they feel the way they feel can open a deep discussion that can be really healthy.”
And while it’s never too early to talk about serious topics (they’re key measures of compatibility, after all), it is important to remain respectful if you bring up something charged on the first date. Worst case scenario: You’re not compatible long-term, and that’s okay! Don’t order that second drink and kindly say you’ve got to turn in early, thanks, goodbye! Best case scenario, you have a robust conversation that keeps you engaged and lets you peek into someone else’s POV for a second. You decide if it’s a deal breaker or not.
5. Display Healthy Empathy
Just like no one wants to be judged for having a different opinion, no one wants to be criticized after sharing something vulnerable. If your date decides to share something deep or personal on a first date, make sure you respond in a supportive way that makes them feel heard and safe enough to continue being honest with you. After all, vulnerability is attractive! It shows that your date felt comfortable enough to open up and is inviting you to learn more about them. Responding with kindness—and, if you feel comfortable, opening up yourself—can help you see different sides to each other, and in some cases, even bring you closer.
“Let’s say I’m out on a date, and my date shares something vulnerable about their childhood,” explains Anderson. “I would want to respond with empathy and validation. A good rule of thumb is to repeat back what you heard and express how it must have made them feel. For example: ‘Losing your dad at such a young age must have been unbelievably challenging. I can see it has made you such a strong person.’”
6. Learn About Their Values and Goals
While asking someone about their hobbies and their favorite memories can go a long way in terms of keeping a conversation going, true compatibility lies in shared values and goals, and it’s good to make sure you’re aligned within the first few dates—especially if everything else has gone well so far and you want to keep seeing them. You can ask directly, or, if you want to be a little more low-key about it, you can go with something like, “I’d love to hear where you see yourself in five years. What do you want to accomplish?” This is a clear pathway to learning what their long-term goals and "dream life" look like.
Another way to learn about someone’s values is to ask them questions about who they’re close to, what their family life looks like, what they prioritize in friendships, and what they look for in the people they date. Questions about their work and what they dedicate their time to can also tell you a ton about what they consider important.
7. Set up the Next Date
If you’ve been chatting online and want to extend the conversation beyond app messaging, texts, or DMs, Los Angeles-based dating and relationships coach Dr. Tara Suwinyattichaiporn, tenured professor of sexual and relational communication at California State University Fullerton, and sex educator on TikTok, says to naturally work in a time to meet up if you feel the conversation is going well. You can say something like, “Would love to tell you more about this story in person! When are you free for a date?” or “OMG, can’t wait to hear more about this. Maybe IRL? When are you around?”
If you’re on a first date already and you already know you want to see them again, “make sure you get the next date scheduled on the calendar. Keep being in each other’s orbit,” says Dr. Tara. You can say something like, “I’d love to hear more about [XYZ topic]. Maybe we can talk about it more over coffee this week?”
8. Play an Ongoing Game
And no, we’re not talking about mind games, like not being the one to text first or waiting a certain amount of time before texting back. We mean an actual game or routine that can give you a natural reason to chat daily. Dr. Tara suggests sharing your “best thought of the day”—initiate it via text one day, and keep it going by sharing the best thought you each had that day. “This allows for vulnerability or humor, and may let each other in on key personality traits or values.”
9. Keep These Questions in Your Back Pocket
If all of this sounds great in theory, but you know that in practice it might be more challenging to keep conversations going, Anderson suggests having the questions below handy. Whether it’s a Notes app note you can scan in the bathroom during a date, or a Post-It you attach to your fridge and refer to before sending that next text or DM. (Just don’t ask them all at once.)
What are you most excited about right now? (This one is great to learn what they’re passionate about.)
What is one of your happiest childhood memories? (To learn more about the things that shaped them in a positive way.)
What do you do to practice self care? (This one can give you insight on their boundaries and what, if anything, they do to intentionally take care of themselves.)
What would your ideal day consist of if anything was possible? (This one can help clue you in on their values and what brings them joy.)
Do you enjoy your career? Why, or why not?
Do you know your love language?
What do you feel like your top three core values are?
What do you do when you’re angry?
What are some qualities you’re looking for in a partner?
What sort of relationship are you looking for right now?
If you stay sincere, open, non-judgmental, and curious, you’ll have a successful conversation, even if you find out there’s no chemistry in the end. Each date is another opportunity to brush up on your dating and communication skills a little bit more, so if a conversation doesn’t go how you want it to, just remind yourself that it’s all part of the process and you’re learning more about yourself and what you want each time you put yourself out there.
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