The Art of the First Text: How to Start Conversations That Lead to Great First Dates

Home » The Art of the First Text: How to Start Conversations That Lead to Great First Dates

Starting the Text Conversation Right

Hey there, I’m Michael Kowalski and I’ve been around the online dating block more times than I can count. In my experience, taking that first step to text a girl you’re interested in can be intimidating. How do you go from matching online to having a fun, engaging text conversation that leads to a real life date? I’ve tested out countless conversation starters and texting strategies over the years. In this article, I’m going to share my proven tips for starting great text conversations with girls you want to get to know.

By following my advice, you’ll learn how to craft interesting opening messages, keep text exchanges going, and turn your online match into an offline connection. I’ll provide plenty of text examples you can use yourself. From thoughtful questions to get the ball rolling to flirty compliments she’ll love, I’ve got you covered. By the end, you’ll have all the tools you need to start meaningful conversations that spark a real connection. Let’s get texting!

Ask Thoughtful Questions That Invite Conversation 

When you first text a match, you want to get the conversation flowing. Yes or no questions won’t cut it. Those kinds of closed-ended questions are conversation killers! You need to ask open-ended questions that spark discussion and get her opening up. 

The key is asking questions about topics she’s genuinely interested in. This shows you want to dig deeper and find out what makes her tick. Go beyond small talk by asking about her hobbies, passions, dreams and opinions. 

Great openers include:

  • “What are you most excited about this summer?”
  • “What’s your favorite way to spend a Saturday afternoon?” 
  • “If you could travel anywhere in the world tomorrow, where would you go?”
  • “What’s the best concert you’ve ever been to?”
  • “What’s something you’re really looking forward to in the next few months?”

See the difference? These questions encourage longer responses and get her engaged in the conversation. She’ll appreciate you taking an interest in who she is and what she cares about. 

So don’t waste those first texts on boring questions. Ask open-ended questions that give her room to share her interests, goals and desires. This lays the groundwork for an engaging, two-way text conversation.

Show You Value Her Opinion

Another great way to get a conversation going is to ask her for a recommendation. This shows that you respect her thoughts and are genuinely interested in her input. Plus, she’ll enjoy feeling like an expert and sharing her knowledge with you.

Some fun recommendations you can ask a girl for include:

  • “What’s the best restaurant you’ve tried lately?” 
  • “I’m looking for a new TV show to get into, what should I watch?”
  • “Know any good live music or comedy shows coming up?”
  • “What phone apps do you find yourself using the most?”
  • “I need some new workout tunes – what are your favorite albums to sweat to?”
  • “What’s your go-to order at [local coffee shop]?”

When you ask for her advice, make sure to follow up. Let her know if you checked out the restaurant or show she suggested. Send a text updating her on how you liked her recommendation. This shows you actually listened to and appreciated her input. 

Giving her a chance to offer a recommendation makes the conversation a two-way street. And following up displays genuine interest in learning her tastes and preferences. This thoughtful approach will score you major points.

Show You’ve Been Paying Attention 

One of the best ways to keep a text conversation going is to proactively bring up topics and interests she’s mentioned. This displays that you’ve been listening and recall what she cares about. 

For example, if she said she loves playing tennis, you could ask:

  • “How was tennis practice this week? Learn any new killer serves?”

Or if she talked about an upcoming trip, check in with:

  • “How’s the planning for your Hawaii trip going? Found any must-do activities yet?”

If she’s a foodie, try:

  • “Checked out that new Italian place yet? I’d love to hear what you thought of it.”

Other great ways to naturally work her interests into the conversation include:

  • Wishing her luck before a big game/event 
  • Sending a relevant article or video you think she’d like
  • Making a light joke about something she’s into
  • Asking thoughtful follow up questions 

Bringing up the things she’s passionate about shows effort on your part. It tells her you’ve been paying close attention and remembering the details. This thoughtful, personalized approach will keep the conversation flowing smoothly.

Make Her Laugh with GIFs, Pics and Memes

A great way to keep a text conversation fun and engaging is to send her a cute or funny GIF, picture, or meme. A bit of humor and levity goes a long way. Just make sure any images you send are tasteful and appropriate. 

Some solid options include:

  • Reaction GIFs responding to something she said (like an “lol” or “mind blown” GIF)
  • Memes related to pop culture or current events you’ve discussed 
  • Silly animal photos and videos
  • Funny scenes from shows/movies you both enjoy
  • Random weird or wacky images (like shoes on a cow or a hippo photobomb)

When choosing GIFs, pics and memes, make sure the humor aligns with hers. Pay attention to the kinds of things that make her laugh. And only send images sparingly – you don’t want the conversation to lose substance.

Sprinkling in some lighthearted visuals shows you’ve got a playful side. This keeps things upbeat and makes your chat feel more dynamic. A shared laugh goes a long way towards strengthening your connection.

Make the Conversation Feel Fresh 

You want your texts to feel like they’re part of an ongoing, active conversation. A great way to do this is to say something timely that’s relevant to the current moment. 

For instance, you could reference:

  • The weather (“Loving this warm sunny day, perfect for a walk in the park.”)
  • A holiday or event (“Happy Valentine’s Day! Any fun plans to celebrate?”)
  • A recent news story (“That meteor shower last night was crazy! Did you catch a glimpse?”)
  • A local happening (“Excited for that new burger place opening up downtown?”)
  • Her recent travels (“How was the jet lag after your Europe trip?”)
  • Sports or TV (“I can’t believe they got eliminated! My bracket is totally busted.”)

Tying your messages to what’s happening now makes things feel current, spontaneous and lively. It shows you’re tuned into the world around you both. 

So look for opportunities to connect your conversations to the day, week or season. Timely references keep the texts coming across fresh, immediate and engaging.

Spark Fun and Connection with Texting Games

An engaging, lively way to keep a text conversation going is to initiate a fun texting game. The playful interaction can create humor and give you a chance to creatively connect.

Some texting games to try include:

  • 20 Questions – Take turns asking each other questions to guess a person, place or thing.
  • Would You Rather – Pose silly scenarios and choose between two absurd options.
  • Name Game – Say a name starting with the last letter of the previous name. 
  • Story Time – Alternate texting a sentence or two to collaboratively build a story. 
  • Lyrics Challenge – Send song lyrics and see who can name the tune first.
  • Emoji Translation – Describe a movie, book, etc only using emoji symbols. 
  • Quote for Quote – Go back and forth sharing inspiring, funny or favorite quotes.

The goal is to keep things upbeat and entertaining. Gauge her interest level and don’t force a game if the convo isn’t vibing. With the right texting partner, exchanging some playful messages can strengthen your connection.

Compliment Her in a Thoughtful Way

An excellent text conversation starter is a sincere compliment. Thoughtfully highlighting something you admire or appreciate about her is a huge confidence booster. Just make sure to keep the focus on non-physical attributes.

Great ways to compliment a girl over text include:

  • “That charity event you organized sounded so cool. You’re so good at bringing people together.”
  • “I really admire your dedication to achieving your dreams. That motivation is contagious!” 
  • “You always have the best book recommendations. Your taste is impeccable!”
  • “I love how you’re always positive and upbeat. It’s really refreshing.”
  • “You’re one of the smartest, most insightful people I know. I love getting your take.”

The key is keeping it classy and centered on something unique about her character, talents or quirks. This shows genuine interest in who she is as a person.

When you brighten her day with a thoughtful compliment, it lays the groundwork for a great text exchange. Just avoid anything that seems objectifying or superficial and focus on qualities that really shine through.

Emojis Are Your Text Convo Friends 

Emojis are great for adding color, fun and personality to your messages. When used strategically, they can convey tone and make text conversations feel more dynamic.

Best practices for emoji usage include:

  • Don’t overdo it. Sprinkle in just a few to augment your texts.
  •  Use emojis that match the tone of what you’re saying. A smiley face conveys something very different than the eye roll emoji!
  •  Pay attention to the emojis she uses and reciprocate accordingly. 
  •  Try out emoji combos to mix things up. A thumbs up + smiling emoji adds enthusiasm.
  •  Utilize emoji reactions when appropriate. Like sending a celebration emoji after she shares good news.
  •  Get creative! Emojis you wouldn’t expect, like a frog or mailbox, can show your quirky side.

Overall, emojis make conversations more colorful, expressive and fun. Just don’t rely on them to do all the work. The best texting combines engaging words with well-placed emojis to maximize effect.

Move the Conversation Offline

Once you’ve got a fun texting rapport going, it’s time to steer things towards meeting up in person. After all, the goal of great text conversation is to transition to spending quality time together offline.

When asking a girl to hang out, keep it low-key and casual at first.

Some smooth ways to propose a meetup over text include:

  • “I’d love to keep chatting more in person. Want to grab coffee this weekend?”
  • “My friends and I are getting together for bowling and beers on Friday. Come join!”
  • “I remember you said you love live music. Want to check out this cool new band playing downtown tomorrow?”
  • “There’s an awesome scenic hike I’ve been wanting to try. It Would be fun to go explore it together.”
  • “What’s your schedule look like next week? Let me know if you’d be up for dinner or something.”

The key is to suggest a casual, low-stakes first meetup. Don’t come on too strong by proposing an elaborate all-day date. Keep it simple and let her vibe guide timing. If she seems interested, set a day and time to continue getting to know each other offline.

Take a Chilled Out Approach 

When texting a girl you like, it’s important not to overload her with a bunch of rapid-fire messages. Take a relaxed pace and let the conversation unfold organically.

Only send one text at a time, and give her a chance to respond before you follow up. If you bombard her with a dozen messages in a row, it can come off as needy or intense. 

Keep things chill by:

  • Not double/triple texting if she hasn’t responded yet
  • Matching the cadence of her texting rhythm 
  • Letting some time pass between back-and-forth volleys  
  • Giving her space to initiate texts sometimes too
  • Avoiding overwhelm by keeping messages concise

The goal is to establish an easygoing, genuine texting dynamic. Rushing things or texting excessively can sabotage the flow. Exercise a little patience and let your connection build slowly but surely.

With a relaxed, one-text-at-a-time approach, your conversation will unfold in an organic way. This sets the stage for a blossoming texting relationship that feels fun, comfortable and full of promise.

Missteps to Steer Clear Of

While texting a new match, there are a few common blunders you’ll want to avoid. Stray from these texting faux pas to keep the conversation positive and moving forward:

One-word responses – “lol” “ok” “nice” – don’t further the convo. Give her sentences and questions to work with. 

Anything inappropriate or overly forward – sexting, flirting aggressively, sexual innuendos – will totally turn her off. Keep texts PG. 

Texting excessively late at night – she may be asleep and conversations can easily misconstrued when it’s late. Stick to normal waking hours.

Asking boring questions like “how’s your day?” – be more original than these dull standbys everyone uses.

Not paying attention to her responses – don’t just talk about yourself. Engage with what she shares to display active listening.

The first conversations you have over text set the tone. You want to establish positive vibes from the start. Keep your texts focused, thoughtful and conversational to get off on the right foot. 

With a bit of care and consideration, you can craft great text messages that capture her interest and spark an exciting new connection.

Texting Tips FAQs

Should I text a girl I just met, or call her?

Texting is usually the way to go when you’ve just gotten a girl’s number. Calling can feel overly formal for an initial outreach. 

Pros of texting first:

  • Easier to break the ice in writing 
  • She can respond on her own time
  • You can craft thoughtful messages 

Pros of calling:

  • More personal 
  • You can gauge verbal interest/tone
  • Shows extra confidence

It’s fine to call later on once you’ve established texting rapport. But at the start, messaging her shows respect and enables an organic back-and-forth.

Does a girl like it if I know a lot of things about her? 

It’s flattering when you can demonstrate you’ve been paying attention to what she shares. But take care not to overdo it too soon – that can come off as creepy. 

Show interest, not obsession. Use the personal details she provides to thoughtfully engage her, not to weirdly impress her with the minutiae you’ve memorized.  

Focus on organically using what you learn about her hobbies and interests to start meaningful conversations. This shows genuine interest in who she is.

What are some “hot” questions to ask?

Universally engaging “hot” questions show your curiosity about her dreams, aspirations, opinions and quirks.

Examples include:

  • “What’s your biggest goal you’re working towards right now?”
  • “What’s something you geek out over that most people don’t get?” 
  • “If you could live anywhere in the world, where would your dream home be?”
  • “What’s on your bucket list this year?” 
  • “What’s something you believe that you think the opposite of most people?”

Thoughtful questions that invite her to share things she’s passionate about are always winning conversation starters.

Let the Conversations Flow

Starting a text conversation with a girl you’re interested in takes finesse. But going in armed with engaging questions, lighthearted humor and genuine compliments gives you a winning formula.

Remember to:

  • Ask open-ended questions that invite her to share
  • Make her laugh with memes and GIFs when appropriate
  • Compliment her in a respectful, thoughtful way
  • Keep texts concise; don’t overdo it
  • Move the conversation offline at the right moment
  • Avoid common texting faux pas

If you focus on listening, tailoring your messages to her vibe and exchanging positive energy, texting success will follow. With the right balance of charm, humor and consideration, you’ll be well on your way to dates that turn great texts into even greater in-person connections.

The texting stage is just the starting point for building a meaningful relationship. Approach it with care and her messages will light up your phone in no time.

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