Anna brings a surprising guest along when she pays a visit to Damon. Elena and Stefan go on an awkward double date with Caroline and Matt, but Stefan and Matt find they have some common ground. Jenna reunites with her old friend Kelly, and Jeremy’s relationship with Anna takes an unexpected direction.

original airdate-- April 1,2010                     rating 2.80 million

Songs: Theme song "Help I'm Alive" by Metric

1.  "Better Than This" – Keane
2.  "Cloudhead" – In-Flight Safety
3.  "The Ocean" – Teagan & Sara
4.  "Cross My Heart" – Marianas Trench
5.  "Perfect Day" – The Constellations
6.  "Crash" – In-Flight Safety
7.  "Lovesick Mistake" – Erin McCarley
8.  "The Mess I Made" – Parachute