How do you start a conversation?

For most of us, texting multiple people throughout the day is as normal as brushing our teeth or fixing dinner after work. We don't necessarily think about the thousands of tiny bubbles we've sent between loved ones over the years—we just continue building on them, one response after another. That is, unless, we've received a new number and the message screen is blank. Now, you need to figure out the right conversation starter text to send.

"Starting a text conversation depends on the scenario," Carmelia Ray, an online dating expert and advisor to the WooYouApp, says. "You want to be really mindful of the personality type and communication preference of the person."

Meet the Expert

• Carmelia Ray is an online dating expert and celebrity matchmaker. She's an author and certified dating coach who co-hosts iDate, the largest online dating, date coaching, and matchmaking conference in the world.

• Lisa Concepcion is a dating and relationship expert and certified life coach through the Institute of Professional Excellence in Coaching.

• Robyn Koenig is a relationship expert and an ICF credentialed Certified Professional Coach. 

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The Pros and Cons of Texting

We all know that the ease of texting makes it the preferred choice for simple conversations or for multitasking, and experts say it can help introverts especially manage interactions. Most of us are experienced with the downsides of that convenience, too, which Ray calls the "misrepresentation and misunderstanding" that occurs when tone and context are lost. Case in point: A Psychology Today article writes just seven percent of communication happens through the content of the message, while everything else happens through body language, vocal tone, emphasis, and pitch.

Similarly, there are some conversations that are better off having over the phone or in-person. Take it from relationship expert Lisa Concepcion. "My rule of thumb is, if you can't express something in two easy sentences, then it's too heavy a topic for text. Pick up the phone and have a conversation," Concepcion says.

Either way, when it comes to building a relationship with someone new—romantic or not—texting, when used in tandem with other forms of communication can be useful... and fun! However, it has to start somewhere. The challenge is how to start a conversation over text.

If you just scored someone's digits—whether it's platonic or romantic—our experts offer some tips to keep in mind when beginning a conversation through text. We also touch on what not to do when texting someone new, because we all know the unique frustration of an unanswered text, too.

Don't Start a Text Conversation This Way

Most experts we talked to agree to avoid potentially heavy topics and to save them for the phone or an in-person conversation. According to Concepcion, stay away from "heavier topics about your relationship status, your past hurts, personal victories and disagreements or misunderstandings which can easily be taken out of context." Similarly, "When you are texting back and forth and think to yourself, 'Why are we not talking on the phone?' then this may be the time to ask if you can call," Ray says.

Ray adds, "You also want to absolutely avoid statements that are sexually explicit in nature unless that is your only goal. Initial texting conversations should always be lighthearted, inspirational, inquisitive, and fun to create a friendly and engaging open dialogue." Be sure to also steer clear of cliche topics of conversation. Making a comment about the nice weather is not going to move the conversation along very much. Other things to be mindful of when texting someone new? Your tone, use of emojis, and when the text conversation is over. Says Ray, "Some people like to text forever and you may not be in a space or time to do that. Always have a plan to politely end your communication."

After your initial texts, you may realize that the conversation isn't going anywhere. Perhaps it's taking your recipient an extended amount of time (a day or longer) to respond. Or when they do respond back, they are not particularly engaged in the conversation. This might be apparent based on their terse responses ("yeah, uh huh, k," etc.). Another sign of a dead end is when you're the only one initiating conversations. Receiving no response at all after a couple of texts is also probably a sign that you should move on. A conversation is only useful (and fun) if both sides are engaged. If it's a one-way street, it's okay to end the chat. 

Text Conversation Starters

As a rule of thumb, texting someone new means keeping things light and involves back-and-forth dialogue about shared interests, finding common ground, and learning about who they are, says Ray. "It takes some time getting to know someone's communication style and may be best to ask in the beginning, 'So are you a texter, or do you prefer to talk on the phone?' or 'Can you text at work, or when is the best time to text you?'" Relationship expert Robyn Koenig adds, "The key to conversation starters is to be interested in the other person without coming across as anxious or desperate for attention. Keep it light and show you have a genuine interest by reaching out with questions that allow for responses beyond one word."

Use this list of 33 conversation starters to jump-start your next text thread with someone new:

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What do you have planned this weekend?

This conversation starter serves two purposes: It allows you to get an idea of their interests while enabling you to suggest a rendez-vous if their schedule is open.

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How would you describe yourself in three words?

Maximum insight in minimal characters.

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How do you relieve stress?

Are they the type who never misses a day at the gym, or do they find zen through binge-watching TV? Either way, knowing how a person winds down is as important as understanding what keeps them going.

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What's your sign?

True, this question can come across as a corny pick-up line, but knowing their zodiac sign can give you a glimpse into their personality. Plus, you can do some research into their sign's compatibility with your own.

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Who have you been friends with the longest and how did you meet?

If they're willing, this text conversation starter may encourage a dialogue about their childhood, including their family life, their hometown, and how they ended up where they are now.

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What was your first concert?

They may be embarrassed to divulge their past musical interests, but that's part of the fun.

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Did you see that viral YouTube video about [insert topic]? What did you think?

If you share a meme or video that made you crack up and they don't have a similar reaction, it could be a clue that you don't share the same sense of humor.

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What did you want to be when you were younger?

If they were able to realize their dream, ask them more about who or what contributed to their success.

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Who's your role model?

What qualities or achievements do they most admire in their role model? See if they think they share any of the same traits.

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What's the high point of your day so far?

If they're having an all-around crummy day, reply with some funny gifs or a link to a silly YouTube video.

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Working on anything exciting at the moment?

Don't limit this leading question to professional initiatives. It's possible that they're working on a creative project outside of work, like redecorating their bedroom or training their new dog.

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What do you bring with you everywhere and anywhere you go?

Are they the sentimental type who always keeps a childhood memento in their pocket? Or are they more pragmatic, preferring to limit essentials to their phone and wallet? This conversation starter for texting might give you a peek into what they think is really important.

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What's the most interesting thing you've read recently?

If they haven't read any good books lately, suggest some of your favorite authors.

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What makes you nervous?

Spiders, public speaking, Zoom calls... Whatever their response, ask them to talk about their coping mechanisms for anxiety (or lack thereof).

Keep the conversation going by asking open-ended questions instead of questions that can be answered with a quick yes or no.

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What's your pet peeve?

Are they irked by loud gum-chewers or bad email etiquette? It's always nice to commiserate about life's daily annoyances with someone who gets it.

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Do you have any hidden talents?

You may not find out about their photography, singing, or poker skills unless you ask.

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What else can you tell me about your post on [Instagram/Snapchat/Facebook/etc.]?

If you're connected with them on social media, ask them to share more details about one of their more recent posts. For example, you could ask about a delicious-looking meal they posted, or ask where they were when they uploaded that sunset photo.

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What's one thing you always do before bed?

Maybe they meditate, listen to a podcast, or pamper their skin. Follow up with more questions about their favorite daily rituals.

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Were (or are) you a good student?

Don't neglect to ask about their favorite and least favorite subjects. This conversation starter for texting allows you to learn more about their work ethic and their interests in one fell swoop.

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If you could outsource one thing in life, what would it be?

Is it cleaning, laundry, cooking, grocery shopping, or something else altogether? Ask how they would spend that extra time.

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If you came with a warning label, what would it say?

There's likely to be a little truth to their reply, even if their response is in jest.

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How did your [interview/meeting/workout class] go?

This text conversation starter shows that you were paying attention during a previous conversation, and allows you to share in their achievements or failures.

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What's your favorite food?

Go back to basics with this text conversation starter. You could reply with your favorite restaurant for that food or cuisine, and invite them to join you for a low-key lunch or more intimate dinner.

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Can you help me choose between [X] and [Y]?

Even if you don't really need their help to decide what to wear tomorrow or what to eat for dinner tonight, you're showing that you value their opinion.

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What was your first impression of me?

As long as you're cool with the potential for a snarky response, this text conversation starter is always good for a laugh.

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If you could travel anywhere in the world right now, where would you go?

Is it a place they've visited before, or is the destination on their travel bucket list?

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What's an emoji that sums up your day so far?

Reply with a few questions about what happened to result in that smiley or sad face.

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What's your favorite movie?

How many times have they seen it? Bonus points if they provide their favorite line from the flick.

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What's your favorite place in your home?

Their answer may hint at their homebody tendencies, or let you know that they're more of an extrovert.

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Hey! Let's get together—when are you free so we can meet up?

Skip the small talk and get right to the point with this text conversation starter. After all, even the most riveting text conversation can't compete with the connections that can be made during an in-person hangout.

31 of 33

You did an amazing job earlier today.

If you really want to win your crush over, use this as an opportunity to send a compliment. From praising them for a presentation well done to commenting on their great style, a few kind words can go a long way when establishing a conversation.

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What's your opinion on the latest [X]?

Ask them for their expert opinion on a topic that they know well. Be it an art exhibition opening, a new film, or a highly anticipated album release, odds are they won't be able to resist sharing their thoughts.

33 of 33

So, when are we going on our next date?

Keep the witty banter going by throwing in a flirty text to indicate that you want to continue your conversation in person. Insert a winking face emoji to seal the deal.

Try These Failsafe First-Date Conversation Starters on Your Next Night Out

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