Fun and flirty ways to start a conversation with a guy over text.

27 Ways To Start A Conversation With A Guy Over Text (+ Examples)

27 Fun and flirty ways to start a conversation with a guy over text. How to start a conversation to keep your crush interested and wanting more.

Figuring out ways to start a conversation with a guy over text can be nerve racking. You want to come across as cool and confident, without being cheesy. But what to say to him?

In real life, smiling and saying a simple “Hi” is about all you need to get a conversation started. Unfortunately, texting doesn’t work that way.

Saying “Hi” lacks imagination and is boring and dull. Not to mention that it doesn’t give your conversation any real flow at all.

How To Start A Conversation With A Guy Over Text - Lead with confidence!

Making a good first impression by sending him that first text is important. That’s where this handy list of conversations starters to text him comes in. You can use these to help ensure that your conversation gets off to a great start.

After you get the ball rolling with a great opener, the ball will be in his court. Then depending on how he replies. You’ll be able to gauge his level of interest. As well as, if it’s going to be the start of a good match, or not.

How To Start A Conversation With A Guy Over Text

1. Lead With Confidence

Yes, sending the first text is bold. But, it also shows major confidence, and you aren’t afraid to go after what you want. You may feel nervous about it or be asking yourself….”Is it even ok to text him first?”.  And yes, sending off that first text can feel intimidating. But the truth is that it’s totally ok to message him first. Even if you just met.

However, you don’t want to over do it. And be the one putting in all the work. All of the time. After you initiate, you have to give him the space that will allow him to come to you.

For more on the do’s and don’ts of texting a guy first read my post here.

how to start a conversation with a guy

2. Make Your Texts Original And Engaging

These days you have to be a savvy texter to stand out from the crowd and get your crushes attention. That means that your text to him should be engaging and interesting. Days of the “Hey”, “Hi!!”’ and the “How are you?” texts are just no longer an option.

Besides being utterly boring, these types of messages can be a total turn off. In fact in one survey conducted by OkCupid, found that sending someone a “Hey” message is totally ignored by users a whopping 84% of the time. (1)

Instead opt for something original, with a little more pizazz. With the goal being, that whatever message you send, it gives him something he can easily and quickly reply back to.

For a example a flirty message like the examples below are a cute way to initiate a fun conversation:

  • “Is it just me, or was the way we met unbelievably cute?” Is a flirty bold opener.
  • “You won’t believe what happened to me today….” Is an example of a cliff hanger text that will definitely pique your crushes attention.

For a list of cute messages and ideas about what to talk about with a guy over text check out our post – 130 Flirty Text Messages To Send To A Guy That You Just Met (Best Of The Best Examples)

Ask him open ended questions

3. Ask Him Open Ended Questions

The goal is to have him text you back, and keep the convo going right? Then the best way to do this is to ask him a question that will spark conversation. One way to do this over text is to ask him an open ended question.

Open ended questions are questions that can’t be answered by a “yes’ or a “no” or some such other one word answer. Open ended questions give the conversation somewhere to go. Instead of falling flat and fading.

They are also a good way to show your interest in getting to know him better.

For example if you send your average run of the mill question like “How was your day?” . You will more often, than not, get an answer like “Good”, “Ok” or “fine.”

Instead text him an open ended question such as:

  • “What was the best part of your day?”. This prompts him to text you back and share something specific.
  • “What’s your opinion on the latest (Album/Movie/Book/Artist)?” (Pick a topic that you know that they really enjoy a movie, Netflix series, book etc.)?

Which in turn, gives you something you can easily respond to and the conversation alive and flowing.

Find Common Ground With A Shared Interest

4. Find Common Ground With A Shared Interest

One the best ways to strike up a conversation with a guy you like is to bring up shared interests or experiences.

A love of the same music, books, or a passion for tacos?  Whatever it is there’s a cute and interesting opener there.

A few examples of light and casual texts that you can send him to find out what you have in common are are:

  • “What’s your guilty pleasure? I’m not ashamed to admit that I’m watching “Love Is Blind” right now :)”
  • “I checked out that band you told me about. You’re right, they DO make the perfect dance music!”
  • “I feel like I’ve seen everything on Netflix. Have you watched anything cool lately?” (You can also use a movie, books, music, etc.)

5. Ask Him For A Recommendation

People love sharing their recommendations. If you know he’s into music, ask which album you should listen to next. If he’s a foodie, you can ask him, which restaurant has the best Sushi in town. Or what his favorite neighborhood hot spots are. The sky’s the limit really.

  • “I went to ( x place ) last night, the food was amazing! Any more recommendations? **smiley face emoji**”

From there, who knows? You may even find yourself agreeing to a date at one of his (or your) favorite spots around town.

How to Start a Conversation Over Text (And Make It Interesting)

6. Text Him A Pop Culture Reference

Sometimes sending something unexpected is one of the best ways to start a conversation. For instance, a pop culture reference could be just the ticket to a fun and engaging exchange for both guys or girls.

For example, you could surprise him by asking that age old question

  • “Did Ross and Rachel ever really break up?”

Then see what happens next.

7. Go For The Puppy (Ask Them About Their Pet)

We’ve all heard that a man’s stomach is the way to his heart. But the next best thing is of course, man’s best friend. Either his dog (or his cat). So if you know he has a pet you can always use that as a starting point to initiate or keep the convo going.

For example:

  • “I adore dogs, pics please..:)”
  • “What usually attracts you to somebody? For me, it’s always a man with a sense of style and a love of dogs/cats…:)”

Besides, everyone loves to talk about their pet. It’s a simple and yet interesting topic that is perfect if you’re ever stuck for what to talk about with a guy over text.

And it also naturally gives your exchange with him somewhere to go.

Be bold! Starting the conversation shows your confidence.

8. Send Him A Bold Message!

Show your interest and confidence by outright acknowledging that you’re making the first move. A modern woman who goes after what she wants. And couldn’t give a toss about outdated texting rules.

How To Approach A Guy Through Text (Example)…

  • “Since we had such a great conversation last night, I decided to bypass the three-day rule and text you.*smiley face emoji*”
  • Good morning! This cute gif/meme reminded me of you. I hope this starts your morning of with the cutest smile! Coffee later?”

9. Send Him A Funny GIF or Meme

Sending a funny GIF or interesting Meme, works like a charm to get his attention. While effortlessly taking the conversation in a fun direction. After all, who doesn’t like getting a funny meme?

Along with the photo, gif, meme etc., text him one of these examples below…

  • “Thoughts?” Or “Why is this so funny to me right now”.
  • Or ask him “What’s your go-to meme?”
  • Send him a funny good morning text for example “Good morning! How you doin?” [then insert a gif with Joey’s sly smile]

A quick word on sending funny gif, meme’s etc. They they work as an opener, because there’s some context for him to respond to. Plus it’s aways nice to show him that you’ve got a good sense of humor.

However, avoid sending just a string of emojis as a conversation starter. As they have much less context, and many people don’t usually know how to reply to them.

In the example below I suggest a better way of using emoji’s as an icebreaker.

For more funny flirty ideas of what to text a guy check out my article here > Flirty Texts To Make Him Laugh

Emoji's can be great conversation starters

10. Use The Power Of The Emoji

Using cute emoji’s are a fun way to help break the ice with that guy you’ve been crushing on. Besides being fun and a bit unexpected. You also have a high probability of getting a reply back from him.

There’s also evidence that people who use emoji’s may have a more satisfying dating life. According to a study based on research from the The Kinsey Institute (2). Where they found a link between those who frequently use emoji’s with potential dates, as having more sex. As well as, a more successful and active dating life. (3)

However you must you this method in a very specific way.

As mentioned above in #8, if you’re just getting to know a guy don’t just send him a string of emojis. Because without any context, he may not know how to reply to you. Instead incorporate the playfulness of emoji’s by using one of the examples below.

Two examples that you can text him to break the ice and start a conversation are…

  • “Which emoji best captures your essence?”
  • “Which emoji’s sums up your day so far?”

Then depending on what he sends, you can start a lively and interesting discussion from that point on.

Pick up where your conversation left off

11. Pick Up A Where A Previous Conversation Left Off

If you’ve communicated before in person, online or over text. Then referencing something that he mentioned in a previous conversation, is a good place to start.

Picking up where you left off last time is an interesting way of naturally continuing the conversation over text. It’s also an easy way to strengthen and build on a previous connection.

You can either send him a message that references something that you talked about that you had in common. Or show your interest in him, by asking him more about a particular interest or hobby he has.

12. Ask Him A Leading Question

If you know a little background about the guy you’re texting then you can ask him a leading question. Then because it’s something that you are sure that he already knows the answer to. It will be easy to get a quick response from him. Once you hear back, your text exchange can evolve from there.

13. Mention Something From His Online Dating or App Profile

Dating profiles are gold mines for conversation starters. You can simply comment on something random he’s written. Or mention a hobby or interest that you have in common. For example, music genres, netflix shows, movies, podcasts, restaurants etc. The list is endless really.

Texting Examples…

  • “I noticed you were wearing a shirt for *X Band.* I love X song, which one’s your favorite?”
  • “Where was that picture of you on a mountain taken? It looks beautiful there.”

And who knows? Once bond over a shared interest, it made even lead to planning a first date.

How To Start A Conversation With Your Crush Through Text

Have a point to your conversation

14. Keep Your Text Brief(ish).

There’s no need to bombard your new crush with a 3 scroll text essay, right out of the gate. Besides, short texts are great openers because create an opportunity for playful banter. Which helps to ensure that your conversation flows. 

So keep it short and sweet. With only a few lines, at most.

15.  Leave Him Wanting More

Always try to end the conversation first. Why? Because knowing when to make a graceful exit, communicates total confidence. Also, that you have something going on with your life. Both of which are very attractive qualities to a high value man.

Besides if you’re the one that always ends the exchange first, then you’re the one holding all the cards. Not just sitting around waiting around for him to reply.

flirty texts for him

16. Have A Point To Your Conversation

When you’re first texting a guy, you want to make sure that there is a point to the conversation. Otherwise your discussion will be more likely to loose momentum and fizzle out. Probably not what you had in mind when conversing with your crush.

Before sending him that first message consider what the point of your discussion will be. That way you don’t get stuck in a typical “how are you” scenario or on cliche topics. That leave the conversation nowhere to go.

This also helps you to feel a bit more in control and less anxious. As you’re getting that first awkwardness out of the way. Ensuring that your exchange with him feels fresh and stays focused.

Text him at the right time of day.

17. Keep In Mind The Time Of Day

Of course you don’t know his schedule, but timing your text is important to consider. For example, sending a first text early in the morning on a weekday may be less likely to reply. And consider this, once all of those emails, and assorted other tasks of a busy work day start piling up. He could even totally forget that you texted him at all.

If you want to send him a text during the work week, I find that the late afternoon or early evening tend to work best. As most of the day will be behind him and you will be more likely to get a reply from him.

These aren’t hard and fast rules. But generally speaking when it comes to weekends, the ideal time to get a reply is mid-morning or early afternoon.

Avoid texting him late at night. Which can make you look needy or desperate. Which of course you are not, at all.

18. Be Mindful Of Tone

Texting isn’t like talking to someone in real life. As the subtle clues that we subconsciously rely on to communicate properly, like tone of voice and body language are missing. And are really hard for someone to infer over text. (4

Which means that your text could easily be misinterpreted. One way to avoid this is to add in a few perfectly placed emoji’s here. Which will help to create more context and tone to your message.

Then next, always make sure to to re-read texts before you send them. Which will ensure that the over all tone is clear and coming across the way you intend it too.

Flirty conversation starters will get a quick reply from him.

How To Start A Flirty Conversation With A Guy Over Text

19. Show Him That You’re Playful With A Flirty Text

Playful banter is one of the quickest ways to strike up a flirty conversation with a guy. Guy’s love this approach and it will almost always get a reply back from him.

Keeping it light and flirty at the beginning, is also a good way of subtly letting a guy know that you like him. As more than a friend.

Though you want to keep in mind that you don’t want to come on too strong. Which could potentially send him the wrong message. So be mindful to stay away from taboo topics. Think classy not trashy.

A flirty text example of what to message a guy to initiate a conversation:

“Watching a movie and the main character looks a lot like you… except, obviously, not nearly as cute…;)”

For more flirty texts and irresistible text message ideas check out our post here >> Clever Texts To Send To A Guy You Like and here >> 200+ Flirty Questions To Ask A Guy (That He Won’t Be Able To Resist)

How Not to Start a Conversation with a Guy Over Text (Don’t Do This!)

20. Don’t Send Him A Bunch Of Texts In A Row

If you’ve already sent him a text then you must resist the urge to send anymore until he responds back to you.

You also want to avoid triple texting, rapid fire texting, or machine gun texting him. Which is when you fire off one text after the other several times in a row.

You may think it’s cute. But it’s more likely to come across as needy and desperate.

 how to have a conversation with a guy

21. Don’t Use His Name

I often see articles recommending that you use someone’s name in a text. Because people love hearing their name and it makes them feel special. While yes, in person and in real life situations that is true. It doesn’t apply to texting (or online messages for that matter).

In fact, after years of studying what works when building new connections in dating, I highly recommend that you don’t use someone’s name in a text. Besides being overly formal and awkward, it sends a subconscious message that you are indeed a stranger.

Think about it this way, when you text a friend do you use their name? No, of course not. That would be weird. Same applies here. Only people that you don’t really know or have any foundation with would ever say your name.

When texting a potential love interest you want your conversation to feel welcoming and natural. So just go head and send him a text like you would when texting a friend.

22. Don’t Send A Sarcastic Text

Laughter is the best medicine. However, when it comes to texts you have to keep in mind that jokes that work in real life don’t always translate to texts. Sarcasm is a perfect example of this. Which often can come across in a text as either snarky or passive aggressive.

Probably not what you had in mind when trying to get a convo going with a new guy.

how to strike up a conversation with a guy

23. Avoid Asking Him To Many Questions

Asking a fun question to begin a conversation is ideal. As well as, asking related questions as you go along. But don’t just send question after question. Because it may make your conversation begin to feel more like an interrogation or an interview.

In addition, make sure that you also share a bit about yourself as you go along. As it also, will give him a chance to ask you a few questions and show his interest in you

24. Don’t Wait Too Long To Reply To Him

When you’re trying to get a fun and interesting conversation going, flow is key. Just like when you’re considering when it will be a good time to send your crush that first crucial message. You also need to make sure, that you actually have time to chat with him over text.

Although, it’s not like you have to reply instantly. There needs to be an opportunity for your convo to flow. This is also important because if he replies to you right away and it takes you hours to reply back. It may come across as being aloof or that you are playing games.

25. Avoid Texting Him Questions On Serious Topics

When starting a conversation with a guy over text, it’s best to stick to openers that are light and playful. Getting into deeply personal details while essential to developing a new relationship, are best saved for in person.

Instead stick to connecting over more lifestyle related topics. Such as work, hobbies, music, books, shows etc.

how to strike up a conversation with a guy

26. Don’t Freak Out If He Doesn’t Respond Immediately

I know that sending a text and not getting a reply back from him right away can feel completely stressful and agonizing. However it’s important to keep those anxious thoughts in check.

Because even though you may have sent a carefully crafted text and timed it perfectly. You don’t know what’s going on with him.

Just because he doesn’t text you back right away, does not mean he doesn’t like you. Or want to reply to you. It just means he’s not available at the moment. He could be doing any number of things.

So take a deep breath and focus on doing something good for yourself until you hear back.

27. Don’t Hide Behind Your Smart Phone

Texting is a great first step for touching base with that guy you’re crushing on. But it’s not ideal for creating the kind of deep connection that lead to a serious long-term commitment.

If you really like this guy, then it’s essential to make sure that you are taking the time to connect in other ways too. Like the phone, or better yet in person on a date.

If you’ve been texting awhile and feel like the conversation is going well. Then don’t be afraid to take it to the next level, by asking him to call you.

Example of How To Get Him To Call You Instead of Text…

“What a great question! You, know, I can talk faster than I can type. Wanna continue this conversation on the phone?…:)”

4 Signs To Move On (& Stop Texting Him)

Understanding how to approach a guy through text is a wonderful skill to learn. However, you want to make sure that you aren’t wasting your time on the wrong man. Here are a few texting signs that he may not be interested in anything serious with you.

1. He Never Texts You First

While it show’s total confidence to send that first message. You don’t want to be doing that every time. Because the truth is that if he’s really interested he will also text you first on a regular and continuous basis.

2. He Runs Hot and Cold

Does he seem to run hot and cold? One week texting you non-stop, then the next you don’t hear from him for days?

If his communication is inconsistent, it could be a sign that not only is he not interested in a relationship with you. And not only that, you might actually just be one of many women that he’s keeping as an option.

3. He Only Texts You Late At Night

The guy that only texts you late at night is in all likelihood one you will want to cross off your list of potential suitors. You probably know the type. The guy that repeatedly asks you for pictures, and sends one word “Heyy!” texts at 11PM. The one that almost always try to turn the conversation sexual too fast.

These guy is the player type that you want to avoid at all costs. Even if he’s cute, funny and successful. Because this behavior is a clear sign that he’s more Player than Prince, and it’s time to move on.

4. He’s Not Moving The Relationship Forward

Texting is a great way to signal interest to a guy that you’ve had your eye on. But from there it’s vital to take a step back and see if he starts to come to you.

If he’s interested in you, he will consistently reply back within a reasonable amount of time. He will ask you questions and seem genuinely interested in getting to know you.

He will move the relationship forward by making plans and taking you on dates. If he’s not doing that. Well then it may be time to consider that he’s not interested in anything serious with you.

Related – Should I Text A Guy “Thank You” After A First Date?

How To Start A Text Conversation With A Guy

Learning different ways to start a conversation with a guy and approach him through text is an essential part of modern dating. Though you may feel shy or intimidated, remember that making that first move is actually very attractive. Messaging him first helps you stand out from the crowd, and shows him that you’re a totally confident woman.

And one last piece of advice? Try not to overthink it. Getting to know a new guy should be fun! Don’t let worry or anxiety take over, by getting caught up in trying to send him the perfect message. Even if it all goes sideways, you can always try again with a different guy.

And if it does well? Well that that’s great, you’ve successfully learned a new skill! And you now know 27 amazing ways to start a conversation with a guy over text.



PS. Want to meet a high quality man? Get your complimentary guide 44 Places To Meet A High Quality man Click Here.

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Save this list of 27 Different Ways To Start A Conversation With A Guy Over Text (+ Fun & Flirty Examples) by Dating Coach & Relationship Expert Deanna Cobden for on Pinterest…

27 Smart ways to start a conversation with a guy over text.

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