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The Viall Files

E1033 Ask Nick - My Boyfriend's Dark Secret

The Viall Files

Nick Viall

Society & Culture, Relationships, After Shows, Tv & Film

424.2K Ratings

🗓️ 17 November 2025

⏱️ 104 minutes

🧾️ Download transcript

Summary

Our first caller's ex won't stop lurking on her IG stories. Our second caller is dating a man with a very dark past. And, our third caller is torn over whether to revive a dead-and-buried friendship with her ex–bestie. 

 

"You have to accept the fact that his past is going to be extraordinarily triggering for your friends and family."

 

Listen to Humble Brag with Cynthia Bailey and Crystal Kung Minkoff every Monday. Available wherever you get your podcasts and YouTube: https://www.youtube.com/@humblebragpod 

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Timestamps:

(00:01) - Intro
(1:07) - Caller One
(28:55) - Caller Two
(1:22:11) - Caller Three

 

Episode Socials:
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Transcript

Click on a timestamp to play from that location

0:00.0

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You're crazy. mobile for details.

2:28.8

How's it going?

2:31.0

Good. What's your name?

2:32.1

I'm Ashley.

2:33.1

How old are you, Ashley?

2:34.0

32. How can I hope? So I dated a guy about five years ago, broke up just because of circumstances, mostly due to distance. We've dated other people in the last five years. And in between relationships, we've kind of always reached out to each other and checked in on each other to see what was going on, see our situation status.

2:56.6

And we've always been in other relationships when the other person is single.

3:02.0

So it kind of has always flip flopped back and forth.

3:05.3

Most recently, after my most recent relationship, I reached out to him.

3:10.3

He told me he was seeing somebody and I wished him the best and I left it at that.

3:16.1

But I've noticed lately that she's been watching my Instagram stories here and there while not following me.

3:25.9

So kind of feels like there's some unresolved thing there.

...

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