Casey: Date 6  (The Matchmaker) episode artwork

EPISODE · May 21, 2026 · 39 MIN

Casey: Date 6 (The Matchmaker)

from The Dating Debrief

After a rough week and a brief pause from dating, Casey and Rachel sit down with celebrity matchmaker Alessandra Conti for an unfiltered deep dive into modern romance, dating burnout, and why finding love in Los Angeles can feel impossible. Alessandra breaks down the patterns keeping both women stuck in chaotic dating cycles, and offers honest advice about chemistry, commitment, and the kinds of men they should actually be looking for. The conversation gets hilariously candid as the girls unpack past flings, dating app disasters, emotional attachment, and the difference between exciting love and stable love, all while Alessandra attempts to map out their romantic futures in real time.  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

After a rough week and a brief pause from dating, Casey and Rachel sit down with celebrity matchmaker Alessandra Conti for an unfiltered deep dive into modern romance, dating burnout, and why finding love in Los Angeles can feel impossible. Alessandra breaks down the patterns keeping both women stuck in chaotic dating cycles, and offers honest advice about chemistry, commitment, and the kinds of men they should actually be looking for. The conversation gets hilariously candid as the girls unpack past flings, dating app disasters, emotional attachment, and the difference between exciting love and stable love, all while Alessandra attempts to map out their romantic futures in real time.   See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Casey: Date 6 (The Matchmaker)

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How long is this episode of The Dating Debrief?

This episode is 39 minutes long.

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This episode was published on May 21, 2026.

What is this episode about?

After a rough week and a brief pause from dating, Casey and Rachel sit down with celebrity matchmaker Alessandra Conti for an unfiltered deep dive into modern romance, dating burnout, and why finding love in Los Angeles can feel impossible....

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