Ask Polly

Ask Polly

'I Cheated on My Fiancée Fifteen Years Ago. The Guilt Has Ruined My Life.'

A closer look at your emotional rebellion will uncover the honorable desire to be seen clearly and loved deeply at the core of your existence.

Heather Havrilesky
Jan 29, 2026
∙ Paid
Weeping Woman (1937), Pablo Picasso

Dear Polly,

Is it possible to forgive yourself? If so, how and when? It not, how do you live with yourself?

Fifteen years ago, my fiancée discovered I was having an affair. She broke off the engagement and immediately moved out. She sent an email detailing every way I’d broken her trust and the damage I’d done. She said …

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