The point is not a magic line. The point is a conversation that gives the other person enough context, energy, and trust to keep moving.
The goal is not just getting a “yes” today. You also want the plan to feel good tomorrow, a week later, and when you actually meet.
Maryam
Open You: “Hey Maryam, fingers crossed you’re this bold in person too 🤞” Her: “Haha we’ll see. I fall a lot actually” You: “Good, gives me something to laugh about on the trail”
Emotional Relevance You: “You seem like the kind of person who picks the hardest trail just to prove a point” Her: “Not wrong lol” You: “I respect the chaos. Also slightly concerned for my knees”
Connection You: “So what do you do when you’re not falling off mountains for fun?” Her: “I’m a nurse, believe it or not” You: “Okay that actually tracks. Steady hands, reckless hobbies”
Progress You: “I know a trail that’s less likely to end in an ER visit. Want to check it out this weekend?” Her: “Depends, are you buying coffee after” You: “Only if you don’t fall on me”
The shape here matters more than the words. Open light. Give her a flirty read on who she is. Learn one real thing about her. Then turn that into a plan.
Sam
Open You: “Sam, your gym selfie is doing a lot of talking. What’s the actual workout, or is that just for the photo?” Her: “Rude. It was leg day, I was suffering” You: “Well, it suits you”
Emotional Relevance You: “You seem like the type who counts reps out loud and scares everyone around you” Her: “I mean… yes” You: “Terrifying. I like it”
Connection You: “What got you into it? Doesn’t seem like a casual hobby at your level” Her: “Played sports growing up and never really stopped” You: “Makes sense. Competitive people don’t know how to sit still”
Progress You: “There’s a spot near me with a solid gym and better coffee than yours. Want to trade workouts for a date sometime this week?” Her: “That’s a strong pitch” You: “I’ve been working on it”
Notice the Progress step never comes out of nowhere. It only shows up once she has shared something real.
Taylor
Open You: “Taylor, that outfit in your third photo belongs on a runway, not a dating app” Her: “Ha, thank you, I actually work in fashion” You: “Called it before you even said it”
Emotional Relevance You: “I bet you judge other people’s outfits and are too polite to say it out loud” Her: “Guilty as charged” You: “I’m going to need a full review of mine at some point”
Connection You: “What’s the part of the job nobody guesses? Everyone thinks it’s all red carpets” Her: “Mostly deadlines and coffee, to be honest” You: “The glamorous burnout industry. Respect”
Progress You: “I’ll let you judge my whole wardrobe in person if you’re free Thursday” Her: “That’s bold of you” You: “I have nothing to hide except maybe one questionable jacket”
Taylor’s chat runs a bit longer before the ask. That’s fine. Some chats need one more back and forth before Progress feels earned.
Heather
Open You: “Heather, is that your dog in photo two? Or did you borrow the cutest dog alive?” Her: “That’s my baby, Biscuit” You: “Biscuit has main character energy, I can tell”
Emotional Relevance You: “You seem like the teacher everyone secretly loves but who acts strict” Her: “How did you know” You: “Lucky guess. Also a little bit of a compliment”
Connection You: “What grade do you teach? I’m picturing chaos and glitter” Her: “Third grade. You’re not wrong about the glitter” You: “A saint. Genuinely”
Progress You: “I’d love to hear more Biscuit stories over coffee. You free this weekend?” Her: “Only if Biscuit gets a shout-out in your profile after this” You: “Deal”
Four women, four openers, one sequence. Open. Build emotional relevance. Find a real connection. Then move it forward.
Next Guide:
A-Z Gameplan from Match to Date A step by step guide on how to go from a match to a date.
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.