Dear Sugars

Episodes We Love: 'Head Or The Heart' Update

Dear Sugars

Show Notes

This episode was originally published on August 12th, 2016.

The Sugars hear the latest from "Head or the Heart" -- a woman who'd fallen head over heels for a man with a troubled childhood. Everything seemed perfect, and yet, she couldn't help but wonder if the traumas of her love's past would surface at some point in their relationship.

"Head or the Heart" became the first letter-writer ever to join the Sugars on the show. The Sugars asked her to write to them in six months to let them know how -- and if -- things were going with her boyfriend. Nine months letter, she sent an update.

So, are they still together? Have any of his past traumas manifested in their relationship? The Sugars find out.

More from Dear Sugars

Oct 3, 2026

This episode was originally released on June 11, 2018.

Sep 19, 2026

This episode was originally released on May 5, 2018.

Aug 29, 2026

Whether you’re 5, 15, or 50 years old, it can be difficult to usher a stepparent in and out of the family unit. In today’s episode, the Sugars answer letters from stepchildren who have fraught relationships with their stepparents.

Aug 7, 2026

In this first episode of "You Could Make This Beautiful," actor Henry Winkler tells hosts Maggie Smith and Faith Salie about the poetry he's found in everything from fly fishing, to the music of Lin-Manuel Miranda, to the acting performances of the late Robin Williams.

Aug 7, 2026

In this second episode of You Could Make This Beautiful, hosts Maggie Smith and Faith Salie talk to Peter Sagal, host of the NPR news quiz show Wait Wait... Don't Tell Me! about a prophetic reading at his first wedding, the poem that has haunted him throughout his life, and about the poetry he's found in the kindness and grace of his children.

See all episodes →