"Our first caller went on 50 dates last year and still hasn't found her person…so what is going wrong? Our second caller is done playing games and wants to know if it's finally time to bl"> "Our first caller went on 50 dates last year and still hasn't found her person…so what is going wrong? Our second caller is done playing games and wants to know if it's finally time to bl"> "Our first caller went on 50 dates last year and still hasn't found her person…so what is going wrong? Our second caller is done playing games and wants to know if it's finally time to bl">
The Viall Files
The Viall Files

E1090 Ask Nick - 50 First Dates and Still No Boyfriend

Mar 09, 2026 · 1h 41m

<p dir="ltr">"Our first caller went on 50 dates last year and still hasn't found her person…so what is going wrong? Our second caller is done playing games and wants to know if it's finally time to block her situationship for good. And our third caller is stuck in an impossible position: her best friend's boyfriend is, and I quote, 'the world's biggest piece of shit,' and she has no idea how to show up for her friend without losing her …

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