Ted and Lily
1996, their first year of college
Ted and Lily have been friends since their freshmen year of college. Lily was dating Ted's roommate and future best friend, Marshall Eriksen. During their college years, the three would hang out with each other on a regular basis, and based on flashbacks, it seems that they spent a lot of time getting high together. Ted was even present when Lily lost her virginity to Marshall. After knowing each other for years, Ted and Lily have become very close, for example, the two have both learned how to tell when the other is lying. The two have a tradition that when they're mad at each other, one of them buys the other a beer to make up. Her engagement to Marshall is what sparks Ted to start looking for a wife. For the majority of the first season, the two's friendship is strong, until Lily breaks off her engagement to Marshall to go to an art fellowship in San Francisco. Ted sees Lily's decision as selfish and takes Marshall's side. Even after Lily and Marshall get back together, Ted still does not completely forgive Lily straight away, due to the fact that he feels that she not only left Marshall, but him as well, and she never apologized to him. The two do eventually make up and Lily still continues to try to help Ted find a wife.
One such episode which features tension between the two is How Lily Stole Christmas. In this episode, they actually have a fight because of something that took place during the summer when Marshall and Lily were broken up; when Ted was helping Marshall to move on from Lily after she left him, he called her a "grinch" (Future Ted reveals that he actually used a word much worse than "grinch"). Lily is horrified when she finds out, but Ted is still not ready apologize, and even calls her a "grinch" again after that. However, they make up at the end of the episode.
Ted and Lily (along with Marshall) first met in their first week of college in September, 1996, and have been best friends ever since. Once in college, when the pair were high together, Lily told Ted that she always wanted an Easy-Bake Oven, but never got it because her feminist mother got her a Lego set. Later, Lily did get it for Christmas, but that was only because Ted told Marshall about it.
In Season 1, Ted helps Marshall practise his proposal to Lily, which she accepts. Lily later helps Ted with Natalie, giving him advice on how to get her to give him a second chance (although she was angry at him at first for the way he dumped her when they were together the first time). They begin to encounter problems in their friendship when Lily decides to move in with Marshall and Ted in The Duel, as Lily makes changes throughout the apartment, much to Ted's dismay. Lily also turns to Ted in Milk after she decides that she wants to go to San Francisco for an art fellowship.
- Milk - Lily turns to Ted when she can't confide in Marshall about her wedding fears.
- The Scorpion and the Toad - Ted warns Lily not to break Marshall's heart again.
- How Lily Stole Christmas - Ted and Lily fight because Ted called her a "grinch" when she was in San Francisco. Ted is angry that Lily never apologized to him when she left.
- Aldrin Justice - Ted gets Lily a job at his firm.
- How I Met Everyone Else - Ted and Lily's first meeting which may not have gone as Lily and Marshall remember.
- The Front Porch - Ted learns that Lily has been sabotaging his relationships.
- The Leap - Lily helps Ted realize he should take the job as a professor.
- Duel Citizenship - Ted gets annoyed when Marshall asks Lily to go on a trip, which was only meant for him and Ted.
- Jenkins - Ted tells Marshall that he would beat him up if he tried to cheat on Lily.
- Say Cheese - Ted brings a girl to Lily's birthday party. She forgives him when she recalls how he welcomed her back in college.
- The Exploding Meatball Sub - Lily tricks Ted into going to the airport with her and tells him that she going to Spain to take some time off as she is getting tired of supporting Marshall.
- The Stinson Missile Crisis - Ted gets too involved in Lily's pregnancy.
- Karma - Ted moves out of the apartment, leaving it to Marshall and Lily.
- The Stamp Tramp - Ted tries to dispel Lily's claim that he has never sealed his own stamp of approval and piggybacked on everybody else's ideas.
- Band or DJ? - Ted and Lily confess to each other how hard a time they are having lately.
- Something New - Lily accompanies Ted to see his house in Westchester which has finished renovating. However, Lily sees a "For Sale" sign, and Ted tells her that he is selling the house, and moving to Chicago to find the love of his life there. Lily tries to talk him out of it but soon realizes that reason Ted is moving is because he doesn't want to be around Barney and Robin after they are married.
- The Poker Game - Lily thinks Ted didn't get her and Marshall a wedding gift. She forgives him after finding out Stuart stole it.