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How to Start a Conversation Over Text: 15 Ways To Kick-off Banter

You think we’d all know how to start a conversation over text by now, but it’s intimidating. Learning how to start a text conversation takes practice.

text conversation - how to start a conversation over text

Depending on your personality, texting may be easier or more difficult than an in-person conversation for you. When you are face-to-face, things can flow more naturally. However, over text, you may overthink and feel the need to plan out what you’re going to say. So, knowing how to start a conversation over text is vital. 

Do you start with a simple “hey” and hope it takes off from there? Or do you go in with a question or share a funny meme?

Who are you texting?

There is no one rule or method that applies to everyone you may be texting. If you’re texting someone for the first time, it will be different than starting a follow up conversation or chatting up a friend.

Before going in with a pick up line or dirty joke, take into account how well you know this person and what sort of conversation will feel natural.

[Read: How to not be a boring texter and keep anyone you chat with interested]

How to start a text conversation calmly

Before I offer you tips on how to start a conversation over text, try to relax. This is just a text. If it doesn’t inspire a full-on conversation, you’ll survive.

I know sending that text can seem so risky, but it doesn’t have to be. Sure, texting may be our #1 form of communication now, but that doesn’t mean it is perfect.

Take a breath. Think about what you want to say and it will all be okay.

How to start a conversation over text

Once you’ve calmed down, start by knowing that this is something everyone worries about. We have all at one time or another wrote out a text, went back, deleted it all, and replaced it with a simple “hey what’s up.”

No one wants to come off clingy or too interested. On the other hand, you also want to have a conversation so saying, “hi,” won’t cut it. You have to find a happy medium depending on your relationship with that person.

[Read: 15 easy text conversation starters for the shy and socially awkward]

1. Are you texting someone new? 

When it comes to knowing how to start a conversation over text with someone new, that is probably the most challenging. If you didn’t meet at school or work, you may not have anything in common to offer a reason for reaching out.

Be unique. Instead of starting with a “hey, what’s up?” try something that makes you stand out a bit. If you’re hoping to make a plan out of this conversation, maybe something like…

“Hey, it’s *your name here*. I had a great time meeting you the other day. There’s a new restaurant opening around the corner from me. They’re supposed to have the best cheese fries if you’d like to go sometime.” [Read: How to ask someone out over text and get that satisfying yes]

2. Just want to talk?

If you’re texting someone new, but don’t want to commit to meeting up, try something more playful and interesting to get a conversation going. Even something as simple as, “I was watching The Office, and something Michael Scott said reminded me of the other night.”

Adding a glimpse of your hobbies or interests into your first text will give them something to latch onto to carry on the conversation. It can also welcome follow up questions. Say you mentioned just getting back from a weekend away, you can then talk about traveling. [Read: 40 questions to ask your crush to subtly flirt with them]

3. Are you texting someone from work?

If you recently got a mutual friend’s number, say a coworker or peer, reaching out should be easier. You have common ground to walk on, so to speak.

You can go in asking about a work project, clarifying something your boss said, asking for some notes you missed, or even bringing up something a mutual friend said. This all makes starting a conversation a bit less nerve racking. It shows you have a reason to reach out on top of just wanting to chat. [Read: How to not be a boring texter and keep anyone interested]

4. Can you woo a friend?

Probably not with one text, but with a series of fun and flirty conversations… maybe so. If you have a crush on a friend of yours, avoid texting them the same way you normally would. That will only push you further into the dreaded friend zone.

Try something subtly flirty. Even a simple compliment like, “You looked great yesterday,” puts a less platonic spin on the conversation. You can also go for the go to, make them laugh. Try a meme or link to a funny article.

Or you could come all out and make it obvious that you are looking to advance your friendship. Send them a BuzzFeed list or quiz about being stuck in the friend zone and see if they pick up on that less than subtle hint. [Read: How to text flirt with a friend and subtly seduce them]

5. Want to reach out to the person you’ve been dating?

Knowing exactly how to start a text conversation with the person you have only just begun dating can be confusing. Do you go straight in all comfy like you’re official with a “Hey, babe?” Or do you hold back? 

No matter what, never say, “Sorry if I’m bothering you.” This message in and of itself is bothersome and annoying. It shows you have a lack of confidence and question this person’s interest. So even if they say something like “sorry, busy right now.” Respond with a “No worries, talk later.”

You want to remain confident, but not too enveloped or else you can come across a little needy. Start with a question regarding something you’ve discussed before. Ask how that meeting at work went or if their mom had a nice birthday. This not only shows you listen but are invested in their life too. [Read: How to keep a text conversation going when you have nothing to say]

6. Want to reach out after a fight?

Sending the first text after a fight can be awkward. You don’t know if the anger has blown over. You aren’t sure if you can go in with humor or how exactly to measure the situation.

If you want to start a text conversation after a fight, whether big or small, an apology is a great place to begin. It doesn’t have to mean you admit you were wrong, but just that you feel bad that you fought and want to work it out. [Read: The first fight in a relationship and what to do next]

7. Can you start a conversation after radio silence? 

Just like texting someone new, starting back up after weeks, months, or even years of not talking can easily go array. Either the person won’t answer, will be curious where you’ve been all that time, or will actually want to talk.

The best way to go about this is to come straight out with the facts instead of trying to hide it. Saying something like, “Hey, I know it has been a long time since we talked, but I wanted to see how you are” is a great place to start.

You could also start this conversation with an old picture you may have found or reboot news on a TV show you know they love. Anything that would show that something reminded you of them will feel more natural. [Read: How to make conversation over text so you’re never boring]

8. Trying to reach out to someone who is ghosting you?

This is something I’ve researched a ton in my younger years. Wanting to talk to someone who is ignoring you is part of human nature. You want to know what you did wrong or why they ghosted.

Will they apologize? Will they ignore the fact that they’ve been so rude? If you are trying to do this, I’m sorry, but don’t. I know you didn’t want this answer, but it isn’t worth it. If this person can’t send a simple text, they aren’t someone you’d want to date or have in your life. [Read: Being left on read – what it means when they don’t text back and what you need to do]

9. Do you feel guilty for ignoring someone?

If you were the ghoster and feel badly for being so rude, starting a text conversation can be awkward. Now, the fact that you feel bad is a good thing. It shows you have a heart, unlike many people who ghost.

If you genuinely feel bad and want to start talking to this person again, own up to it. Say that you are really sorry for ghosting them and hope they’ll give you another chance. Don’t make an excuse or try to avoid what you did. They know and you know.

10. Are you trying to reconnect with an ex?

I very rarely promote this. There is a reason your relationship ended. You may miss things right now, but that is because you’re not together. Unless you have both fixed the issues that broke you up in the first place, it isn’t a good idea.

If I can’t talk you out of it and you’re going to do it anyway, try this… Be honest about why you’re reaching out. Don’t be shy. Don’t act like you just thought of them. If you want to hook up, come out with it. If you want to pick up something you left at their place or have recurring feelings for them, be honest.

There is no point in wasting time beating around the bush. [Read: 11 rules for getting back together with an ex]

11. Do you need something?

If you want to talk to someone because you need a favor, you have to have a balance of kindness and bluntness. Learning how to start a text conversation when you need something is about subtlety.

Be kind and ask how they are. Have a genuine interest in how they’re doing. Don’t wait too long to ask for the favor. This will come off like you’re using them.

Ask for the favor and offer something in return at the same time. Don’t say, “I’ll owe you one.” For example, “I could really use your help moving my couch this weekend. Pizza and beers are on me.”

12. Are you lonely?

If you want to talk to someone because you’re lonely, don’t text someone that could reject you. Don’t reach out to someone that has ghosted you before. Don’t start a conversation over text with an ex or someone you’re in a situationship with. It will leave you feeling worse.

In this case, text a trusted friend, sibling, or even a parent. They will be able to cheer you up and keep you company, even digitally. [Read: Why do I feel so alone? The answers that can change your life]

13. Do you have a topic in mind?

If you already know what you want to talk about, there is no need for niceties. You don’t need to go in with small talk. It is texting, not a work email.

If you want to talk about something awkward that happened or ask a sensitive question, do it. You can preface it with something like, “if you have the time I’d like to talk about something…” This lets them know you want their attention.

But, then jump into it. [Read: Why being blunt can be a great asset]

14. Is it worth it?

If you want to start a text conversation with someone you don’t like, just to fill the time, is it worth it? Are you trying to text someone who always gets under your skin? Why? What will be different this time?

Ask these questions before starting a text conversation, especially with someone that isn’t close to you.

15. Are you still too nervous?

If all else fails, a wrong text fake out is slightly immature, but still a less risky way to go. If you’re scared of rejection or ghosting you can say something you would text a sibling. Something like, “we’re out of milk,” or “I don’t know, ask mom.” They’ll know this text isn’t for them, but it can be an entryway into a new conversation. [Read: The accidental text on purpose – How to use it and when to avoid it]

[Read: 12 clever text messages to get anyone to text back right away]

Knowing how to start a conversation over text is pretty much a must-have skill with the way dating works in this age and time! Follow these tips and just send out your first text, it’s easier than you think!

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Samantha Ann
My name is Samantha Ann. I am 28 years old. It was always my dream to become an advice columnist, so after years of off and online dating and eventually finding...