My Dating Life Was A Mess – Then My Therapist Had Me Do A Bizarre Exercise To Fix It

"My therapist’s exercise might seem out of the box, maybe even a little mean to some, but it did exactly what she had hoped."

When I was 41, my therapist handed me photos of every boy in my fourth grade class and instructed me to condemn each one to the paper shredder. It was my first experience of truly being in the driver’s seat, and I felt giddy with control.

From an early age, I’ve carried an acute fear of rejection and abandonment. This has made dating challenging, to say the least. My typical dating pattern used to be the following: I’d meet someone I liked, become enamoured, only to find myself spiralling into persistent anxiety, worried about when and how the relationship would end.

That sense of unease began in middle school.

The night my friend revealed she had a boyfriend, we were bundled in sleeping bags on chalet bunks, up past curfew during our eighth grade ski trip. She was the first in our group to date.

As the girls clamoured for details (“What does he look like? What school does he go to?”), I should have known something was off when the only question I thought to ask was, “Aren’t you terrified that he’s going to break up with you?”

Although it would be years before I experienced romantic heartbreak firsthand, I now realise that even then, I was already bracing for the worst.

By the time I was older, like anyone who frequents pop psychology circles, I was aware of attachment styles and how early childhood experiences can shape adult relationships. Yet, I grew up in a safe, stable home with parents who didn’t always get along but loved and supported me unconditionally, so I never really understood where this anxiety came from.

This confusion persisted until 2021, when a session with my therapist changed everything.

At that time, I’d booked an appointment because I had just started seeing someone new. It was the first person I’d liked since the beginning of the Covid-19 pandemic, and I’d noticed my usual pattern taking hold again. I was overcome with anxiety over whether........

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