Managed to get it down to 4 retries:
1. S (for "This!")
2. LKEM (for "I like it! I'm going to get one too. Me too.")
3. YAPCUDW (for "Not my thing. A picnic? Nah. That's up to you. Those ones look nice. Hanging out at home. Chilling with my dog. His name is Pumpkin. He's a little shy. Why?")
4. All letters (Ending)