I had this epiphany lately because I know that it is a joke of how unrealistically obsessive the main character is about finding the right one. But I just realised that this is such an obsession of his that he is willing to see almost every woman as a number or a rating (to some degree) based on the likelihood to fill in his personal fantasies of true love or sometimes to fill in his empty whole of loneliness.
And he is more likely to do all kinds of silly and sometimes bizarre things that can be deemed as obsessive or delusional or maybe even controlling.
In our eyes, this is really funny.
But if you look at it deeply, Ted is always willing to go to the extra mile to please girl or many. Or the biggest one, going the extra mile to continue to please Robin (when she should have walked away from him when they stopped dating in order to give each other some distance) when he was told multiple times to move on. But then, even after the mother died, which the show is meant to be after, Ted was still obsessed.
And also, there were moments that Ted was attempting to go the extra mile to fill up his love fantasies that can be seen as controlling like wanting Stella to live in New York or was close to telling a fiance to date him instead based on a dating statistic; or obsessive-compulsive like dressing up as the same costume every Halloween to increase his chances of seeing the Slutty Pumpkin.
We often joke that Barney Stinson is the most juvenile and needs to learn to let go of his inner child and comes to terms with reality and uses all kinds of cunning or even manipulative schemes to get laid.
But I think that Ted Mosby seriously needs a lot of therapy and growing up because he also does all these schemes to fill in clinging fantasies of perfect love.
Sure, the series touches on this and highlights this but this is really delusional and unhealthy and dangerous. Maybe even toxic.