How I Met Your Mother: 10 Worst Breakups

With the benefit of hindsight, the concept of Marshall and Lily not being together forever is laughable.

Still, this was before How I Met Your Mother was a pop culture juggernaut, and before we knew where the series would go. So when the inaugural seasons ends with Marshall on the steps of the apartment in the rain, clutching the engagement ring Lily has given back to him, it is shocking and uncertain how things will play out.

Marshall and Lily are the standard of which all relationships in HIMYM are measured, what Ted aspires to have, what makes Barney and Robin simultaneously disgusted and envious. For it all to have almost ended due a lack of communication and dreams of what could have played out differently in life is hard to come to terms with.

Once Lily and Marshall get back together, they are rock solid. Still, this bump in their fairy tale romance is undeniably the worst breakup examined in the show.

The fact that Marshall reveals he has held onto resentment from this breakup years later drives home just how serious the damage was. Yes, everything works out, and the two will live together for the rest of their lives with three beautiful children. But the summer break between season one and two was unbearable.