Should You Shoot Your Shot?

Billy & Lisa in the Morning42mMarch 31, 2026

Get the full intelligence

Search transcripts, export clips, track mentions, and explore all topics from “Should You Shoot Your Shot?” inside PodZeus.

AI-Generated Summary

The episode of 'Billy & Lisa in the Morning' centers on the theme of taking action in personal relationships, highlighted by a listener's story of successfully 'shooting her shot' at a coworker she had been flirting with. Riley, a producer on the show, shared how she confronted her coworker directly after months of texting and subtle signals, asking, 'Are you just going to keep texting me, or are you ever going to actually ask me out?' The man responded positively, planned a surprise Celtics game date, and the relationship is now progressing with a second date. The hosts celebrate this as a rare, positive story in their usual mix of humorous and dramatic talkback segments. The episode also features promotional plugs for various iHeartMedia podcasts, including the upcoming appearance of Dave Portnoy on Lisa's Book Club, updates on major concerts like Ariana Grande and BTS, and personal stories from artists such as Charlie Puth and Celine Dion. The tone is upbeat and encouraging, emphasizing that boldness in love and life often leads to rewarding outcomes.

Key Takeaways
1

Taking initiative in relationships—like Riley did—can lead to meaningful connections, even with coworkers.

2

Direct communication beats passive flirting; asking for what you want removes ambiguity.

3

A surprise date (like a Celtics game) can be a powerful way to show genuine interest and effort.

4

Being open about your feelings doesn’t mean losing control—sometimes, it gives the other person space to respond.

5

Dating a coworker can work if roles and boundaries are respected and the relationship stays private.

…and 2 more takeaways available in PodZeus

Chapters
0:00
5 min

Podcast Promos and Morning Warm-Up

The episode opens with a series of promotional segments for iHeartMedia podcasts, including Sino Show, The Nick Dickens Poll Show, Math & Magic, Eating While Broke, and others, setting a lively tone for the morning show.

5:00
5 min

Weather, March 31st, and the Match Game Launch

Billy and Lisa welcome listeners with a lighthearted update on the weather, marking the end of March and the beginning of April, while introducing the new Free Ticket Match Game with sold-out concerts from artists like BTS, Ed Sheeran, and Harry Styles.

10:00
10 min

Dave Portnoy Joins Lisa's Book Club

I just sent him a DM and I explained to him what I was doing. I wanted him to come to Lisa's book club and he responded... almost instantly.

Highlight
20:00
10 min

Behind the Scenes of 'See You Again' with Charlie Puth

It felt so special. We all started crying because it felt so special. I fully believe that... maybe that was him throwing the song down to me.

Highlight
30:00
10 min

Riley’s Story: Shooting Her Shot at a Coworker

I said, are you just going to keep texting me, or are you ever going to actually ask me out? Whoa. That is very cool. Sometimes you've got to take it by the reins.

Highlight
High-Impact Quotes
It felt so special. We all started crying because it felt so special. I fully believe that... maybe that was him throwing the song down to me.
Charlie Puth22:03
Viral: 88.0
I said, are you just going to keep texting me, or are you ever going to actually ask me out? Whoa. That is very cool. Sometimes you've got to take it by the reins.
Riley38:45
Viral: 85.0
I'm here tonight to pay my respects to one of my favorite human beings and one of my favorite artists of all time, Miss Nelly Furtado.
Drake27:38
Viral: 80.0
Speakers

Hosts

Billy CostaLisa

Guests

Dave PortnoyJenna Bush HagerCharlie PuthCeline DionRiley (talkbacker)
Topics Discussed
dating and relationships95%taking initiative in love90%workplace romance85%podcast promotions80%concerts and live events75%personal growth and self-acceptance70%storytelling and authenticity65%celebrity culture and fandom60%
People & Brands

Lisa

person

15xPositive

Riley

person

14xPositive

Billy Costa

person

12xPositive

iHeartMedia

organization

12xPositive

Dave Portnoy

person

10xPositive

BTS

other

8xPositive

Jenna Bush Hager

person

6xPositive

Nelly Furtado

person

6xPositive

Charlie Puth

person

5xPositive

Barstool Sports

organization

5xPositive

Get the full intelligence

Search transcripts, export clips, track mentions, and explore all topics from “Should You Shoot Your Shot?” inside PodZeus.

Start discovering podcast insights today

Start with a 7-day trial and explore a growing catalog of popular podcasts. No credit card required.

No credit card required • 7-day trial • Cancel anytime