First Message Tips: How to Start a Conversation Online

Most first messages fall flat for one of two reasons: they could have been sent to anyone, or they ask for too much too soon. Avoid those two and you are already ahead. Here is how to write an opener that feels natural, how to keep the conversation going, and what to do when the reply takes a while.

Anyone can make the first move

There is no rule about who writes first. If someone's profile makes you smile, tell them. Reaching out is not desperate, it is decisive, and most people are pleased to be noticed. The worst that happens is no reply, which costs you nothing.

What to say in a first message

• Mention something specific from their profile: a place, a hobby, a photo, a line that made you laugh.
• Ask one open question that is easy and fun to answer.
• Add a line about you, so it feels like a chat rather than an interview.
• Keep it short. Two to four sentences is plenty.

Three openers that follow the pattern, to adapt rather than copy:

"That photo from the top of the hill looks amazing. Was it worth the climb? I keep promising myself I'll do more walking this year."

"You're learning to bake bread? How's it going? Mine still comes out like a doorstop."

"A fellow fan of terrible films. What's the worst one you secretly love? Mine involves a shark."

What to leave out

• Chat-up lines. The cheesy one-liners that get a laugh in a sitcom tend to land with a thud in a message. Be yourself instead.
• Comments about their body. Compliment something they chose, such as a photo, a phrase or a hobby, rather than how they look.
• Copy and paste. People can tell, and it says they were one of fifty.
• "Hey" on its own. It gives them nothing to reply to.
• Asking for their number or more photos straight away. Let the conversation build first. Keeping it on the site is safer, and Dating Today shows a warning if someone pushes to move the chat to another app such as WhatsApp, a favourite trick of scammers.

Keep your cool while you wait

People are busy. A reply can take a day or two, and sometimes it does not come at all. That is rarely about you: they may be talking to someone else, taking a break, or not checking in. Send one light follow-up at most, then let it go. Talking to a few people at once takes the pressure off any single conversation, and going at your own pace is always allowed.

Keeping the conversation going

Ask follow-up questions about what they tell you, share stories of your own and pick up threads from earlier messages. If the chat runs dry after a few exchanges, that is useful information too.

From messages to a date

Once you have swapped a good few messages and you both seem keen, suggest a short video call. It is the quickest way to check you get on, and it makes the first meeting far less nerve-racking. Then pick somewhere simple: our cheap date ideas and first date tips will help.

More dating advice

• Dating profile tips

  Photos, an honest "about me" and what to leave off.

• First date tips

  Nerves, outfits, conversation and awkward pauses.

• Dating green flags

  The small signs that someone is worth your time.

Common questions

Should I wait for them to message first?

No need. Anyone can send the first message, and a friendly, specific one is usually welcome.

What if they do not reply?

Send one light follow-up at most, then move on. Silence is rarely personal; people get busy or are talking to someone else.

When should I ask for their number?

When you have chatted for a while and both feel comfortable. Until then, keep talking on the site, where you can block or report anyone who makes you uneasy.