Either of you can. The League says there is no rule about who sends the first message, so once you match, the conversation belongs to whoever starts it. If you want the date, that person should usually be you.
Where to send the first message
The chat lives in its own tab, so it is worth knowing exactly where to look.
- Tap the Matches tab. Its icon is a chat bubble with a heart inside it.
- Tap Active.
- Choose her from the list.
- Type your message and send it.
That is the whole process. She does not have to write before you are allowed to, and nothing else has to happen first.
Why you should write first
On an app where nobody is required to go first, two people can sit and wait for each other for a long time. She assumes you will write. You assume she will. A week later, the chat is still blank on both sides.
The League also puts a clock on that silence. A match that nobody writes to expires after 14 days, so waiting is not a neutral choice. Every day you hold back comes off the timer.
a dating coach's advice for any app that lets men write first is to use it. Men who sit back and accept whatever conversations come to them end up talking to fewer of the women they actually want. Writing first also puts you in charge of the tone. She gets to react to something, which is a much easier job than starting a conversation from nothing.
What to say in the first line
The first message does not need to be clever. It needs to be about her.
My method is to go through what she has put on the app and look for anything unusual, anything he could comment on or tease her about. What she wrote usually beats her photos as material. A comment on a photo tends to read as a comment on her looks, and she has heard plenty of those. Picking up on something she wrote proves you actually read it.
Keep it short. If one line says it, do not send three. Keep it light and a little playful, and aim it at the real question behind every first message: are you two going to like each other? "How was your day?" does not ask that. It asks her to fill in a form.
If nothing on her page gives you much to work with, a simple warm line is fine. A plain hello with her name, or an honest compliment, is not needy. What you send after it matters far more.
When she writes first
Sometimes she will beat you to it. That is good news, not a test.
Answer her the same day. Respond to what she actually said, add one small detail about yourself, and give her an easy question back. The worst reply to a woman who wrote first is a slow one, because she took the small risk of starting and then heard nothing.
Pay attention to how she opened. coach noticed that women who start conversations with him tend to react to the same few things he wrote about himself. Once a reply to one of those works, he saves it and sends it again the next time. You can do the same.
Keep a file of lines that work
Most men start every conversation from zero. It is tiring, and it makes their messages worse as the week goes on.
coach keeps a running document of every first message that got a good response and moved toward a date. He groups the lines by the kind of woman they worked on, and when he matches with someone similar, he reuses what worked. Over a few months the file gets better, and writing first stops feeling like a chore.
On an app as selective as The League, this matters even more. Every woman you match with deserves a good opening line, and a file of tested lines means she gets one even on a night you are tired.
Move from messages to a plan
Your opening line is only there to start a conversation that ends with the two of you at a bar. Once she is clearly enjoying the back and forth, suggest something simple, like a drink on a specific evening.
coach treats every chat on every app as a short road to a date, not a place to stay. Get her number, settle a time and a place, and carry on by text from there.
Who sent the first message stops mattering the moment you have a plan. What matters is that somebody did, and on The League that somebody should usually be you.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.