You’ve matched. You’ve looked at their photos. You’ve read their profile (twice). Now you’re staring at the message box wondering what on earth to say.
“Hey” feels too generic. A paragraph feels too keen. A GIF feels… lazy?
Welcome to the first message dilemma—where promising connections go to die before they’ve even begun.
The Problem With Most Opening Messages
After analysing hundreds of conversations on Illicit Encounters, we’ve identified the messages that kill conversations before they start:
The Generic Greeting:
“Hey how are you?”
This puts all the work on them. They’re already taking a risk being here—they don’t want to carry the conversation too.
The Physical Compliment:
“You’re stunning 😍”
Flattering, but it suggests you’ve looked at nothing but their photos. They’ve put effort into their profile—acknowledge it.
The Interrogation:
“What do you do? Where do you live? Are you married?”
Twenty questions isn’t a conversation. It’s an interview. And nobody likes being interviewed at 9pm.
The Premature Intimacy:
“I’ve been looking for someone like you for so long”
You haven’t even met. This level of intensity before you’ve exchanged ten messages sends people running.
What Actually Works
The best opening messages on Illicit Encounters share three qualities: they’re personalised, they’re easy to respond to, and they give something of yourself.
Reference Their Profile Specifically
Instead of:
“You seem interesting”
Try:
“I noticed you mentioned you love hiking but hate early mornings—finally, someone who understands that the best walks start at 11am with a coffee in hand.”
This shows you’ve actually read their profile. It gives them an easy response (their own hiking stories). And it reveals something about you (you’re not a 6am person either).
Ask Something That Requires Thought
Instead of:
“What are you looking for on here?”
Try:
“If you could have dinner with any three people, alive or dead, who would you choose and why? I’m asking because my answer keeps changing depending on the week.”
This is fun to answer. It reveals personality. And it gives you genuine insight into who they are.
Instead of:
“Tell me about yourself”
Try:
“I’ll be honest—I’m nervous about messaging you because your profile actually made me laugh and that doesn’t happen often. The bit about [specific reference]—completely relatable.”
Vulnerability invites vulnerability. And everyone appreciates being appreciated.
Make It Easy to Say Yes
Instead of:
“We should meet sometime”
Try:
“I know a quiet wine bar in [area] that does excellent [specific drink]. No pressure—just if you fancy a conversation that doesn’t involve typing.”
Specific. Low-pressure. Easy to accept or decline without awkwardness.
Real Examples That Led to Dates
Example 1:
“Your profile says you love bad 80s films. I have a confession: I own the complete works of Schwarzenegger on DVD. Is that a dealbreaker or the beginning of a beautiful friendship?”
Why it worked: Humour, self-awareness, easy to respond to.
Example 2:
“I saw you mention you’re looking for someone who understands ‘the situation.’ I do. I’m in the same boat. Perhaps we could compare notes over coffee?”
Why it worked: Acknowledged the context without being explicit. Created immediate understanding.
Example 3:
“You said you like people who are direct. So: I think you’re attractive, your profile made me smile, and I’d like to buy you a drink. If you’re not interested, no hard feelings—but I didn’t want to wonder ‘what if?’”
Why it worked: Confident but respectful. Showed he’d read her preferences. Left her an easy out.
The Follow-Up Rule
Sent a good message and got no reply? Wait three days, then send one follow-up:
“I realise you might be busy or not interested, which is completely fine. I just didn’t want to wonder if my message got lost in the void. If you’re keen to chat, great. If not, best of luck on here—you seem lovely.”
Then let it go. No third messages. No “????”. No guilt trips.
The Golden Rule
The best first message isn’t clever or funny or impressive. It’s genuine.
Say something that sounds like you. Reference something that actually interested you about them. Give them something easy to respond to.
And if they don’t reply? It wasn’t your message. It was their situation, their timing, their unread notifications. Move on. Send the next one.
Because somewhere on here is someone who’s been waiting for exactly your kind of message.
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