Here is my 100% Achievement guide for Episode 1 of Tell Me Why.
First off, there are two locations you can get this.
First is where you get to the ronan household.
As you face the house, you see the barn just on your right, if you go between the house and barn, head down a small banking and go to your right, thats where you should see the bench.
Wait for Alyson to catch up, then interact with the bench using
.
Exhaust both dialogue options and achievement should unlock soon after.
Second location is at the police station.
When you go upstairs and find chief Brown, he gives you a key to go get some coffee in the break room.
You have to go through a locker room before said break room.
In here is where a bench is, so again, wait for Tyler this time. Interact with bench, then exhaust both dialogue options.
Go to 28:40 in the video to see where i get this at the ronan household
Hope This helps!