To start a conversation over text, send a message with a built-in hook: a specific question, a shared reference, or a small story. The formula is context + personality + easy question. “Hey” has none of the three — which is why it kills conversations before they start.
18 texts that start conversations
- I need your opinion on something and it's more important than it sounds.
- You've been in my head today — how are you actually doing?
- Tell me the best thing that happened to you this week. I'll wait.
- I just saw [thing] and had to tell someone who'd get it.
- Weird question: what's your comfort movie? No judgment. Some judgment.
- I'm building the perfect Saturday. What's one thing it has to include?
- You're the first person I thought of when [relevant thing] happened.
- Hot take incoming: [playful opinion]. Agree or fight me.
- What's something you're looking forward to right now?
- I heard [song/show/thing they love] and it's basically your personality in audio form.
- Okay so I have a story. Do you want the short version or the good version?
- If we got food right now, where are we going? Wrong answers only.
- What's your current 3am thought? Mine's keeping me up.
- Life update exchange. You first.
- I found a photo from [shared memory] and now I'm smiling like an idiot.
- Quick, recommend me something — a show, a snack, a life choice.
- On a scale of 1–10, how's your week? I'm at a solid 6 with a bullet.
- You know what we haven't done in way too long? Talked. Fixing that now.
Starting a conversation with a guy vs. your girlfriend
With a guy you're interested in: lead with playfulness — a challenge, a hot take, or a tease gives him something fun to push back on. With your girlfriend: lead with attention — reference something she mentioned this week and ask about it. “How did the meeting with your boss go?” starts more real conversations than any line, because it proves you listen.
Openers to avoid
- “Hey” / “Hi” / “wyd” — zero hooks, zero effort, usually zero reply.
- “Why haven't you texted me?” — starting with guilt poisons the whole exchange.
- Copy-paste energy — anything that could've been sent to ten people at once reads that way.
How to use What2Text to start any conversation
- Open What2Text and choose Start a Conversation.
- Tell it who it's for — crush, partner, friend, coworker — and one detail about them or your last interaction.
- Pick your tone and get three openers with a built-in hook. Copy the best one and watch the typing bubbles appear.
Start conversations that actually go somewhere
What2Text writes personalized openers for any person and any situation — no more staring at an empty chat.
Download What2Text FreeFrequently asked questions
What's the best text to start a conversation?
A specific question tied to the person: their week, their opinion, their plans. Specificity signals genuine interest, and a question gives them an obvious way to respond.
How do I start a text conversation without being boring?
Skip the greeting entirely and open mid-thought: “Okay, I need your take on something.” Starting in the middle of an idea creates instant momentum and curiosity.
How do I start a conversation with my girlfriend over text?
Reference something specific from her life — a work thing, a plan, something she was worried about. For daily texts that keep the connection warm, see what to text her.