The first ghost is the "Ghost of Girlfriends Past" in the form of Allison Vandermeersh (Emma Stone), one of his high school girlfriends and his first lover.
Together, they revisit scenes from his past, focusing on his relationship with Jenny.
In 1982, Connor and Jenny were very close as children; she gave him his first instant camera which he used to take her picture, promising to keep it forever.
When Connor's parents died in a car accident, Jenny consoles Connor throughout the years without them, as she, his brother Paul and his uncle Wayne were all he had left.
Further in the future, Paul is the only mourner at Connor's funeral.
Connor also sees that Jenny is being comforted by Brad (Daniel Sunjata), and is upset that his own actions and attitude are bringing the two closer.By middle school, the two were on the verge of romance, but Connor's hesitation at asking her for a dance caused Jenny to dance with and kiss another boy.Heartbroken, Connor was told by Wayne that he must avoid romance at all costs in order not to feel such pain again.Connor helps Jenny to restart the wedding, which he photographs, and afterwards he reconciles with Jenny by showing her the picture he still carries of her as a child and by promising to always be there when she wakes up.The two kiss and dance in the snow to the same song Connor once hesitated to ask her to dance to.