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HELP! I Suck at Dating

DeAnna’s Going On A Date

HELP! I Suck at Dating

iHeartPodcasts

Health & Fitness, Tv & Film, Sexuality, Relationships, Society & Culture

44.5K Ratings

🗓️ 5 October 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

It's time! Ben is sending DeAnna on her first blind date at the Jonas Brothers concert. Is she nervous? What's she going to wear? Ben is getting the REAL chat before she heads out on her date.

Then later, Ben connects with our spy who is monitoring the date and connecting with DeAnna and the date during the evening.

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

This is an IHeart podcast.

0:04.8

Teamsters president Jimmy Hoffa once promised to break both of Bobby Kennedy's arms.

0:09.8

Bobby, JFK's attorney general, wanted to take down the mob, starting with Hoffa.

0:14.0

Like, no one gives a shit about Bobby, right?

0:16.2

So this is Bobby trying to get the world to care about him, which I think explains all this passion and anger going into this, even though it's all kind of ineptly handled.

0:27.2

On United States of Kennedy, we dive into the hidden stories fueling our cultural fascination with the Kennedy dynasty.

0:33.6

Listen on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.

0:37.6

IHeart Podcasts bring you the ultimate Summer of Love Tree.

0:42.0

This is famously available.

0:44.7

Welcome back to famously available.

0:46.7

I'm your host, Ben Higgins, and I'm really excited about this episode.

0:50.3

Because we've been getting to know our famously available women and let me tell you they are awesome

0:56.7

we got diana and mercedes we've been catching up with them for what seems like months now

1:03.4

and today i'm sending diana on a date in the real world and she's here with me she's looking beautiful looking flirty am i i thought you were going to keep going that's why i paused i was waiting for the multitude of compliments glamorous um looking spunky all these things okay spunky i don't know if i hope this things. Okay. Spunky.

1:31.3

I don't know if I hope this date thinks I'm spunky, Ben.

1:33.3

I think Spunky's a good thing.

1:34.3

Spunky? Okay.

1:37.7

All right. So here we go. This is a lot of fun for me.

1:41.5

We've sent you to San Francisco is where you're currently at.

1:43.3

You're going to a Jonas Brothers concert.

2:01.8

This date will be there with you. I'm very, very excited to ask you. How are you feeling? I am super excited. I have to be honest, the response to the podcast has been really great. But our listeners keep messaging me wanting to know if I'm actually going to date someone.

2:05.8

Like, they're all caught up now and all of the things and they know what I want and what I'm doing,

...

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