In Right Place, Right Time, Barney completes his ongoing mission to sleep with 200 women.
As he sits alone at Mac Laren's, he rips up the list and wonders "What now? In The Leap, Barney confesses his love for Robin to Ted, who isn't surprised.
After agreeing to date him again, he dumps her a short time afterward, the same way he did when they were teens, and Robin is left in a vulnerable state at the bar.
Barney sees her crying and comforts her, saying she's too awesome now as an adult to want to relive her teen years.
In The Stinsons, Barney's mother tells him not to run from a clear shot with someone special and Barney ponders if Robin is that person.
Lily sets them up on a dinner date and despite Barney being on his best behaviour, Robin assumes she's only there to be his wingman, and introduces him to the waitress.
Barney does end up sleeping with the waitress but secretly checks in on Robin's news show every morning just to see her face.
Robin invites Barney back to her apartment to watch her second Robin Sparkles music video 'Sandcastles in the Sand', which Simon starred in.
Robin and Barney watch the tape over and over until they end up having sex.
In , Ted and Robin become "friends with benefits" in order to stop fighting so often, and Barney is extremely distressed.