How to Start a Conversation: Keeping the Chat Going With Someone New

Why do conversations run dry so fast?

The hardest part of chatting with someone new is the first few messages. "Hi", "Hi, how are you?", "Good, you?" — and that's where it ends. Usually it's not that the other person isn't interested; it's that neither of you finds anything to hold on to. Closed questions (ones answered with yes, no or a single word) don't move the conversation forward.

The good news: starting conversations is more a habit than a talent. With a few simple principles your first message gets easier to write and the conversation moves along by itself.

The first message: make it about them

A message you could send to anyone doesn't feel special to anyone. In your first message, mention something from their profile, a post or something you have in common. One of your answers to the same test, a hobby on their profile, a place in a photo they shared — these show you're interested and give them something to talk about.

• "We both chose 'a quiet evening' in this test; what does your ideal quiet evening look like?"
• "The beach in your photo looks lovely, where is it? I love walking by the sea too."
• "Your profile says photography; do you shoot with your phone or a camera?"

Ask open-ended questions

Open-ended questions start with "how", "why" or "what do you like most about" and invite the other person to tell a story. Instead of "Do you read?", asking "Is there a book you read recently that stuck with you, and why?" opens up far more room.

Still, don't fire questions one after another; after each answer, share something of your own. A conversation is an exchange where two people take turns, not a one-way interrogation.

• "If you had no plans at all this weekend, where would you end up?"
• "What did you want to be as a kid, and does it have anything to do with who you are now?"
• "When you visit a city for the first time, where do you go first?"
• "Has anything made you laugh lately?"
• "Is there something you've always wanted to learn but never started?"
• "How does the morning of a perfect day begin?"

Active listening works in text too

Face to face, you nod, smile and say "mm-hmm". In text, the equivalent is really responding to what they wrote. Instead of replying only to the last sentence of a long message, pick up on a detail: "That trip with your brother sounds fun, what moment do you remember most?"

Remembering what they told you is also a strong signal. Asking about an exam or job interview they mentioned a few days ago shows you were listening.

What to do when the conversation stalls

Every conversation has quiet moments, and that's normal. When you feel it stalling, don't hesitate to change the subject. A light "this or that" question, going back to something you share or telling a small moment from your day can bring it back to life.

• This or that: "Mountains or the sea?", "Morning person or night owl?", "Movies or series?"
• Go back to a shared test question: "I'm curious why you picked that answer."
• Share a moment from your day: "I saw the cutest dog on my way home today, how was your day?"
• Ask for a recommendation: "Any film you'd recommend for this weekend?"

Mistakes to avoid

Some habits can cool down even a conversation that started well: one-word answers, talking only about yourself, asking very personal questions too early or making insistent comments about someone's looks. Asking for a phone number, address or social media account in the first messages can also make people uneasy; these get shared naturally as trust builds.

If a reply is slow, it's better to wait than to send message after message. Everyone has a life, a job and busy hours.

Respecting boundaries and ending kindly

Not every conversation has to become a friendship or a date. If you sense they're not interested, or you aren't, saying so kindly saves both of you time: something like "It was nice talking to you, but this isn't what I'm looking for. Good luck!"

If someone crosses your boundaries, sends disturbing messages or won't accept "no", you don't have to keep the conversation going. On Hemdem you can block someone and report a message; a blocked person can't write to you again.

Something in common is the best start

The best ground for an easy conversation is something you genuinely share. That's why Hemdem has personality tests: talking with someone who took the same test about where you think alike and where you differ is a much easier start than "Hey, what's up?". There are no right answers in the tests; what's interesting are the stories behind the answers.