1.

2.

3.

4.

5. 2.12 - Caroline makes Tyler smile

6. 2.11 - Caroline returns

7. 2.11 - The Hug, Tyler then transforms

8. 2.11 - Caroline refuses to leave

9. 2.08 - "How can you be a vampire, How can you be a werewolf"

10. 2.11 - Tyler undresses, Caroline blushes

11. 2.10 - Caroline tells Tyler about her vamp transformation
12. 2.21 - Caroline covers up naked Tyler on the porch
13. 2.20 - Outside The Hospital
14. 2.10 - Caroline tells Tyler she is helping him
15. 2.08 - Caroline shows Tyler her vamp face
16. 2.10 - Caroline and Tyler watch Masons 1st transformation
17. 2.08 - Caroline nearly breaks Tyler's arm
18. 2.11 - Tyler cries "It huts, It hurts"
19. 2.10 - Tyler shows Caroline the Lockwood cellar
20. 2.08 - How do you know about me
21. 2.07 - "I'm fixing a very bad situation"
22. 2.11 - Tyler drinks the Wolfsbain
23. 2.13 - Tyler gets Caroline out of the cage
24. 2.07 - Tyler's first kill
25. 2.21 - Matt shoots werewolf Tyler
26. 2.11 - They arrive in the woods
27. 2.20 - "Who is Klaus"
28. 2.13 - "Stefan and Damon are vampires just like you"
29. 2.11 - Mason never made it to Florida
30. 2.20 - Tyler transforms and bites Damon
31. 2.13 - Caroline slams the door in Tyler's face
32. 2.14 - Tyler tries to apologse to Caroline in the grill - steals her phone

This is getting harder and harder

I love all of them, but I picked this because Caroline wasn't happy at the end of their kiss.