Ted and Lily have a great relationship in How I Met Your Mother - and are a phenomenal example of how sitcoms can show close friendships between men and women (something that is often rare in the genre). From the time that the two met in college to the rest of their lives as friends, Ted and Lily are always there for each other, and support each other through ups and downs, goats and pineapples.
But how would the Ted of the first season feel about the Lily of the finale, and all the things that she goes through over the course of the show? Some of these things he understood, at the time, or forgave her for later, but would Ted be so forgiving about where she ends up if he knew at the start? Or would he just be proud of how far she has come?
Hate: That She And Marshall Became Too Codependent
This is actually something that Ted hates at the time, when Lily and Marshall become 'one of those couples' who can't do anything without the other, and who basically merge into one formless blob of a human. This particularly annoys Ted because it causes problems for his last road trip with Marshall to go to their favorite pizza place before it closes for good, but even without that, Ted would get upset learning just how much of a third wheel he would become.
Proud Of: That She And Marshall Are Sill Together
Ted has been rooting for Lily and Marshall from the first moment that they met, when Marshall was thinking that maybe it wouldn't work out, and Ted encouraged him to give it a chance. He's always believed that they are perfect together (except for a brief period when Lily ran off to San Francisco), so if he learned that they would end up married, happily, and starting a family, he would be incredibly proud.
Hate: The Long Term Bets
In the seventh season of the show, Barney discovers that Marshall and Lily have been making long-term bets on everyone else's life, and unsurprisingly, people aren't thrilled about it.
If season one Ted learned that while he was just enjoying time with his friends, they were betting on him going bald, he would be furious about it!
Proud Of: Repairing Her Relationship With Her Dad
Lily has a difficult relationship with her father, as he was rarely around when she was growing up, and she resents him for it (and for a whole host of other things). However, in the end they do manage to patch things up, and Mickey actually becomes a staple in their lives for a while to help out with Baby Marvin. And although Ted can get annoyed with his own parents, family is important to him- and he'd be proud of his friend for finding a way to forge a relationship with hers as adults.
Hate: That Marshall Had To Do Corporate Law Because Of Her
At the time, Ted was actually understanding about this - and it meant that he and Marshall (and Barney) actually got to work together for a while, which they all loved. However, the Ted of season one knew that what Marshall really wanted to do was to go into environmental law, and if he learned that Marshall would have to give up on this (for a while) to help pay off Lily's debts, he would be furious with her over it.
Proud Of: Her Coming Clean About Her Debt
Much as Ted would be furious that his best friend has to put his dream on pause to help Lily with her debt, he would be proud of her for coming clean about it and actually taking charge of her finances, instead of just continuing to rack up debt on things like shoes to make her feel better when she is sad. Seeing her also try to make something of her art and make extra money to fix it is something that any friend would be proud of.
Hate: Finding Out She Broke Up His Relationships
Later on in the series, it is revealed that whenever Ted was dating someone that Lily found unacceptable for their friend group, she would do something to break them up - usually by leaving something out for the girlfriend to find.
He's livid when he discovers this, and he would be just as unhappy if he learned about it earlier, especially as it really isn't up to Lily who Ted marries (even if they are going to all spend old age together).
Proud Of: Her Art Career
Lily flounders a little bit with what she wants to do with her life, and even leaves Marshall to go try and be an artist in San Francisco - but struggles to really make a career out of it. However, by the end of the series, she has a side business making paintings for vets, and she actually launches a new career as an art buyer for The Captain. While it may not have been the career path as a painter that she expected, Ted would be thrilled to learn that she does manage to find a life in the art world.
Hate: That She Left Marshall
Easily the worst thing that Lily did in the entire series was break off her engagement to Marshall to go to San Francisco, and Ted would definitely hate to hear about it. He would be especially upset to learn that she didn't stay in touch with Ted when she did leave, and didn't apologize to him when she got back. This became a bit point in the series itself, and while it ended up actually reconfirming how close they were, and why Ted was so hurt by this, he definitely wouldn't be happy to know that this was in their future.
Proud Of: The She Is A Great Mom
One of the sweetest and saddest scenes in the show is when Ted admits to Lily on the rooftop that he is in love with Robin - who is happily with Barney at the time. And he does it so that she can say the 'thing you aren't supposed to say' - that sometimes, it's really hard being a mom, and she just wants to run away. Ted is always there to support Lily, but he also does this because he knows that really, she is an incredible mother, and he's always there in her hardest moments to remind her that she is a wonderful mom.