The Real Conversation
She Was Engaged.
I Still Lost Her.
This is the actual conversation that made me build StartTheDate.
She replied. She asked questions. She was already interested —
and I still managed to kill it with two bad pivots.
Name and images changed for privacy.
By Marc-André Gratton — founder of StartTheDate, author of Build The Man, Win The Game
6:21
📶 58%
Today 11:19 a.m.
Hi Sarah, I like your style :)
Thanks. I love style.
Are you a coach?
Yes I coach my son's house league basketball team. How many sit ups can you do?
❤️
⚠ Pivot #1 — She asked about coaching, he answered, then swerved into a gym question with no connection. Lost the thread.
Lol I haven't actually counted but hundreds for sure
My oldest son is 15 and youngest is 12
I have girls the same age
Nice my girls are younger 10-8 😁
❤️
Blessed to have so many little humans to love
Yes very blessed, I'm not looking forward to my girls starting dating.
Sorry 😜, is there dad still in the picture?
⚠ Pivot #2 — Warm moment (shared parenting humour) → immediately asked about her ex. Too personal, too soon.
Ok good, it's important for the kids. What are you looking for?
💀 The conversation ender — approved her co-parenting situation like an interviewer, then asked "what are you looking for?" Felt like a checklist, not a connection.
🚫 Sarah unmatched shortly after.
What actually went wrong
1
"How many sit ups can you do?"
She'd just opened a real thread — coaching, family, kids. There was a natural conversation happening. This question had nothing to do with any of it. It reset the vibe from zero.
2
"Is there dad still in the picture?"
She made a warm, funny comment about her daughter dating. The right move was to stay in that moment — laugh about it, build on it. Instead: a question about her ex. Too heavy, too soon.
!
"Ok good, it's important for the kids. What are you looking for?"
This is the one that ended it. Two problems in one message: "Ok good" reads as approval from a job interviewer, and "what are you looking for?" is the most clinical question you can ask mid-conversation. It signals you've run out of things to say — and it puts all the emotional labour on her.
She was already interested.
The messages lost her.
StartTheDate helps you stay in the conversation — not just start it.
Paste their profile, get a message that keeps things moving.
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