If I remember right, in this moment the three of them are debating who has had the worse luck with women.
I'd have to go with Frasier. He did have that fling with the supermodel zoologist, though.
this post was submitted on 01 Jul 2023
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Yep, you are right: S05E13 - The Maris Counselor.
I wouldn't know if Frasier had the most bad luck. Frasier sabotaged a lot of relationships himself. He is obsessing over the tiniest flaws and if someone is perfect he misses a challenge.
Niles on the other hand just dated awful women.