In the Words of MyCheekyDate
Because the only thing better than a great first date… is the second one.
Speed dating gives you the spark — but the follow-up is where things turn into something real.
And yet, most people wing it. No plan, no timing, no idea what to say, and definitely no strategy.
Here’s the truth: connection is chemistry, but second dates are science.
A little structure goes a long way.
So here it is — our Cheeky, advisor-backed, research-inspired checklist for what to do after a great event to set yourself up for second-date success.
🔬 PART 1 — The First 24 Hours
✨ The “Just Right” Follow-Up Window
Studies on impression retention show that emotional warmth has a half-life of roughly 24 hours.
Translation: follow up while the glow is still warm, but don’t sprint.
✔ Best timeline: 12–24 hours after the event
Enough time to sleep on it.
Not enough time for overthinking to kick in.
Your Message Should Be:
Simple
Warm
Short
Specific
Not a copy-paste of what you tell everyone
Example:
“Last night was fun — I’m still thinking about your take on traveling without an itinerary. Want to grab coffee this week?”
💬 PART 2 — What to Text (And What Not to Text)
✔ The Perfect First Message Should:
Reference something specific from your chat
Be low-pressure
Invite connection, not commitment
Show personality
Offer a simple next step
✘ Avoid Messages Like:
“WYD” (your connection deserves more than a placeholder)
“So what are you looking for?” (save it for in-person)
Essays (no one wants your memoir at 9AM)
Dry logistics: “When are you free?” (too transactional)
Think of texting as the bridge, not the destination.
🕰 PART 3 — The Follow-Up Timeline
A science-backed pacing guide
✔ Day 1
Send the first message.
✔ Day 2–3
If they reply warmly, keep the conversation light.
Think “smile-worthy,” not “job interview.”
✔ Day 3–4
Suggest the second date.
Make it easy to say yes.
Example:
“I found a wine bar that does flights and tiny snacks. Want to check it out this week?”
✔ Day 5–7
If things feel good, confirm a day and time.
✔ After the Second Date
If it was great?
Say it.
Humans are terrible at guessing (and overthinking).
🧠 PART 4 — What to Talk About (Advisor-Approved)
✔ Topics That Build Connection:
Travel stories with personality
Aspirations (but not 5-year business plans)
Firsts (first concert, first job, first big laugh)
Foods you’d fight someone over
“What’s something you didn’t expect to enjoy this year?”
✘ Topics That Kill Momentum:
Trauma dumps
Exes
High-pressure future talk
Work rants
Cryptic “I’m so complicated” monologues
Taxes (please, no)
Great second dates feel like a comfortable movie you want to keep watching.
❤️ PART 5 — Our Official Cheeky Second-Date Checklist
Before You Message:
✔ Do you actually want to see them again?
✔ Do you remember something specific they said?
✔ Are you texting because you want to — not because “you should”?
When You Message:
✔ Keep it light
✔ Personalize it
✔ Mention something they said or did
✔ Suggest something simple and fun
When You Plan:
✔ Choose a place with great lighting & low noise
✔ Keep it under 90 minutes
✔ Pick something you would genuinely enjoy even if the date goes nowhere
✔ Have a plan but stay flexible
During the Date:
✔ Show up on time
✔ Be warm, not performative
✔ Ask questions that make them smile
✔ Match curiosity with curiosity
✔ Put your phone away (unless you’re photographing a dog)
After the Date:
✔ If you liked them, tell them
✔ If you want a third date, ask
✔ If you’re unsure, that’s okay — sometimes attraction builds
✔ If it’s a no, be kind, be clear, be human
💛 At the End of the Day…
Second dates happen because two people choose to show up — with intention, kindness, curiosity, and a little courage. (Okay, and sometimes good hair.)
Speed dating gives you the spark.
The follow-up turns it into something real.
And with a little science and a little cheeky structure, you’ll be miles ahead of the “WYD” crowd.
Connection isn’t complicated — it’s consistent.
And consistency builds everything worth having.