50 Fun, Flirty, and Unique Ideas

When you develop a crush, you experience a number of tell-tales: flushed cheeks, an ever-present smile, and a desire to learn everything you can about that person. Luckily, in the age of digital communication, texting allows you do just that. Instead of waiting until your next in-person interaction to ask for their thoughts on, well, everything, you can send them a message. However, even though such a possibility exists, that doesn’t mean that figuring out what to say or how to say it is an easy feat. And as a result, you may be eagerly searching for good conversation starters for a texting conversation.

Before you start drafting lines and stressing over your capitalization, consider the context of your relationship. “Starting a text conversation depends on the scenario,” says Carmelia Ray, an online dating expert. “You want to be really mindful of the personality type and communication preference of the person.” For example, some people may prefer to chat over the phone versus over text—while others may want to develop your relationship exclusively through in-person dates. None of these approaches are right or wrong; it’s simply about understanding how your partner prefers to communicate and seeing if that complements your own preferences.

Below, experts offer key tips to keep in mind when messaging something new, as well as offer some of the best conversation starters for such a conversation. Make sure to read these important reminders before hitting send.

Should You Text Someone You’re Interested In?

It depends on what you plan to say. There are numerous benefits to texting, including it being an easy and quick form of communication, as well as its ability help certain people, particularly introverts, manage social interactions. However, this type of digital back-and-forth also comes with some downsides. It’s much more likely that someone will misunderstand your tone or context over text than during an in-person conversation.

There are also certain discussions that are better over the phone or in person. “My rule of thumb is, if you can’t express something in two easy sentences, then it’s too heavy a topic for text,” says Lisa Concepcion, a dating and relationship expert. “Pick up the phone and have a conversation.” When it comes to building a relationship with someone new—romantic or not—texting, when used in conjunction with other forms of communication, can be useful. However, the challenge is often figuring out how to start a text conversation.

What to Avoid When Starting a Text Conversation

Avoid potentially heavy topics when starting a text conversation. Instead, save them for the phone or an in-person meet-up. According to Concepcion, this may include discussing “your relationship status, your past hurts, personal victories and disagreements or misunderstandings which can easily be taken out of context.” Make sure to reflect on the nature of your dynamic prior to hitting send. “You also want to absolutely avoid statements that are sexually explicit in nature unless that is your only goal,” Ray says. “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 cliché 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 conversation is over. “Some people like to text forever and you may not be in a space or time to do that,” Ray says. “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, they’re not engaged in the conversation. Maybe this is clear based on their terse responses (“yeah, uh huh, k,” etc.) or the fact that you’re the only one initiating conversations. Ultimately, receiving no response at all after a couple of texts is likely a sign that you should move on.

50 Conversation Starters for Texting Someone New

When texting someone new, keep things light. Focus on having a back-and-forth dialogue about shared interests, find common ground, and learn 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?'” Even if you’re excited about your budding dynamic, try to play it a bit cool. “The key to conversation starters is to be interested in the other person without coming across as anxious or desperate for attention,” says Robyn Koenig, a relationship expert. “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 50 conversation starters to jump-start your next text with someone new:

Ask Them About Their Life

• How would you describe yourself in three words?
• How do you relieve stress?
• What’s your sign?
• Who have you been friends with the longest and how did you meet?
• What did you want to be when you were younger?
• Who is your role model?
• What is the high point of your day so far?
• What do you bring everywhere you go?
• What’s one thing that makes you nervous?
• What’s a pet peeve of yours?
• What’s one thing you always do before bed?
• Did/do you enjoy school?
• If you came with a warning label, what would it say?
• What’s your favorite thing about your hometown?
• What’s your biggest accomplishment?
• How do you define success?

Ask About Plans, Interests, or Activities

• What do you have planned for this weekend?
• What was your first concert?
• Are you working on anything exciting at the moment?
• Do you have any hidden talents?
• I’d love to hear more about your recent post on [Instagram/Snapchat/Facebook/Twitter]!
• If you have an hour of free time, how do you typically spend it?
• How did your interview/meeting/workout class go?
• What’s your absolute favorite food?
• If you could travel anywhere in the world right now, where would you go?

Ask About Pop Culture

• Did you see that viral YouTube video about [insert topic]? What did you think?
• What’s the most interesting thing you’ve read recently?
• What’s your favorite movie, and how many times do you think you’ve seen it?
• What’s your opinion on the latest [X]?
• What song do you have on repeat lately?
• I just finished watching [X], and I think you’d love it!
• What are your thoughts on social media?

Ask Them About Their Thoughts on You

• Can you help me choose between [X] and [Y]?
• What was your first impression of me?
• What’s an emoji that you think describes me, and one that describes you?
• What’s something that surprised you about me?

Make Plans

• Hey! Let’s get together—when are you free so we can meet up?
• So when are we going on our next date?
• What do you think we should do for our next date?
• I have an extra ticket to this concert, do you want to come with me?
• Hey, want to try out that restaurant in town that just opened?

Compliment Them

• You did an amazing job with that [interview/meeting/event] earlier today.
• Do you want to know something I really like about you?
• I really enjoyed our conversation about [X] the other day.
• I can’t get your smile out of my head.
• I’ve been thinking about you.

Lead With Humor

• What’s the worst pick-up line you’ve ever heard?
• What’s the most embarrassing thing that happened to you in your recent memory?
• What’s your plan for the zombie apocalypse?
• Hit me with your best dad joke.