It was no surprise that Lily and Marshall continued to grow their family, but nothing else went according to plan. Barney and Robin divorced just a few years into their marriage, and the titular “mother” character had passed away when Ted’s story reached the present. Ted and Robin found their way back to each other in the series finale, but they, along with the rest of the cast, could have easily ended up with someone else.

Lily Aldrin – Robin

Robin admitted she never got along well with other girls, but Lily was the exception. They loved each other deeply, and friendship is a great stepping stone to any romance. If Lily and Marshall hadn’t ended up together, she and Robin would have been a good match.

Barney Stinson – Quinn

Barney and Quinn loved each other for who they were, and there wasn’t much of an explanation for their lack of trust. They were both cynical and untrustworthy people, but oddly, it’s what made them fit together perfectly. There was no judgment on either side, and their relationship was going well until it ended abruptly. Quinn didn’t fall for Barney’s tricks, and she gave him a taste of his own medicine.

Marshall Eriksen – Brad

There was a point when Marshall decided things needed to end but was surprisingly disappointed when he discovered that Brad had gotten back together with his girlfriend. They formed a rivalry down the line, but Brad eventually came back to Marshall’s side. A relationship between them would never be boring, and they worked in the same field.

Robin Scherbatsky – Barney

Barney was Robin’s only real option other than Ted. She didn’t have many long-term romances, and the few she did have never felt quite right. How I Met, Your Mother proved that Barney and Robin would never work out after their marriage resulted in a divorce, but things could have quickly gone a different way.

Ted Mosby – Victoria

Ted and Victoria’s relationship was easy to love, and there was something about them that always felt right. Robin was the reason for their breakup, and if Ted had moved past his feelings, he and Victoria would have gone through with their engagement.

Tracy McConnell – Cindy

There was only one person other than Ted that viewers knew Tracy to have loved, but he passed away when Tracy was in her early 20s. Tracy’s roommate, Cindy, dated Ted briefly, but Ted’s apparent interest in Tracy prevented them from working out.
However, it was later revealed that Tracy was the person Cindy was romantically interested in, which explained why she was so upset every time someone fell in love with her. If Tracy hadn’t become Ted’s wife, she should have been introduced as the girl who would eventually marry Cindy.