In this episode of If You Knew Better, Amber Grimes sits down with actress Gail Bean for an honest conversation about love, loyalty, and learning to date with greater intention [00:00]. Gail reflects on why she stopped leading people on when she knows there’s no romantic interest [01:10], the importance of establishing clear boundaries with platonic male friends [04:18], and how to receive or give compliments without creating confusion [06:45]. She explains how her approach to relationships evolved toward intentional dating [08:18], distinguishing preferences from true non-negotiables while identifying the difference between red flags and undeniable “sirens” [11:17]. After taking a year to reflect on herself and past relationships [16:10], Gail revisits a serious relationship where love was sometimes used to overlook deeper problems, ultimately realizing that love alone isn’t enough without loyalty, character, accountability, and shared values [18:00]. She also discusses accepting responsibility for your role in relationships [19:40] and why healthy love should challenge both partners to evolve [21:30].

Gail then opens up about what changed when she chose a partner capable of leading with intention, consistency, and purpose [22:48], redefining what genuine support looks like beyond money or surface-level gestures [27:03] and sharing communication tools that help strengthen their relationship [29:04]. She takes Amber inside their origin story [31:04] and explains how dating intentionally [32:24] eventually became what she calls “defensive dating”—asking important questions early about monogamy, finances, exes, and other potential complications instead of discovering deal-breakers later [34:14]. Gail also emphasizes listening to trusted friends and family [35:51], creating accountability through honest relationship check-ins [37:39], and how greater stability in her personal life has coincided with elevation in her career, including becoming number one on the call sheet [39:07]. She closes with reflections on choosing relationships that encourage growth, provide emotional security, and prove that who you build with can influence who you ultimately become [40:24]. 

Ask or Share with Amber:withambergrimes@gmail.com

Follow Amber Grimes on Instagram:

@ambergrimes

Follow Gail Bean:

@gail_bean

Get Amber's Newsletter on Substack

Watch This Episode on Youtube Thursday at 6pm ET 

Follow Amber's Book Club 

Get Amber's Book Club Merch 

Read Amber's Favorite Books

In this episode of If You Knew Better, Amber Grimes sits down with actress Gail Bean for an honest conversation about love, loyalty, and learning to date with greater intention [00:00]. Gail reflects on why she stopped leading people on when she knows there&rsquo;s no romantic interest [01:10], the importance of establishing clear boundaries with platonic male friends [04:18], and how to receive or give compliments without creating confusion [06:45]. She explains how her approach to relationships evolved toward intentional dating [08:18], distinguishing preferences from true non-negotiables while identifying the difference between red flags and undeniable &ldquo;sirens&rdquo; [11:17]. After taking a year to reflect on herself and past relationships [16:10], Gail revisits a serious relationship where love was sometimes used to overlook deeper problems, ultimately realizing that love alone isn&rsquo;t enough without loyalty, character, accountability, and shared values [18:00]. She also discusses accepting responsibility for your role in relationships [19:40]&nbsp;and why healthy love should challenge both partners to evolve [21:30].
Gail then opens up about what changed when she chose a partner capable of leading with intention, consistency, and purpose [22:48], redefining what genuine support looks like beyond money or surface-level gestures [27:03]&nbsp;and sharing communication tools that help strengthen their relationship [29:04]. She takes Amber inside their origin story [31:04]&nbsp;and explains how dating intentionally [32:24]&nbsp;eventually became what she calls &ldquo;defensive dating&rdquo;&mdash;asking important questions early about monogamy, finances, exes, and other potential complications instead of discovering deal-breakers later [34:14]. Gail also emphasizes listening to trusted friends and family [35:51], creating accountability through honest relationship check-ins [37:39], and how greater stability in her personal life has coincided with elevation in her career, including becoming number one on the call sheet [39:07]. She closes with reflections on choosing relationships that encourage growth, provide emotional security, and prove that who you build with can influence who you ultimately become [40:24].&nbsp;
Ask or Share with Amber: <a href="mailto:withambergrimes@gmail.com" data-ogsc="">withambergrimes@gmail.com</a>
Follow Amber Grimes on Instagram:
<a href="https://www.instagram.com/ambergrimes">@ambergrimes</a>
Follow Gail Bean:
<a href="https://www.instagram.com/gail_bean/">@gail_bean</a>
<a href="https://substack.com/@withambergrimes">Get Amber's Newsletter on Substack</a>
<a href="https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0">Watch This Episode on Youtube Thursday at 6pm ET&nbsp;</a>
<a href="https://www.instagram.com/ambersbookclub/">Follow Amber's Book Club </a>
<a href="https://ambersbookclub.com/collections/hats">Get Amber's Book Club Merch&nbsp;</a>
<a href="https://a.co/d/01GreLFP">Read Amber's Favorite Books</a>

You can’t rewrite the past — but you can learn from it. Amber Grimes did exactly that, going from college dropout to Executive Vice President in the entertainment industry with no map, just mistakes and lessons that turned into power moves.

 

If You Knew Better is where Amber shares that wisdom — alongside artists, creatives, and culture-shifters who open up about the missteps they made, the mindsets that changed everything, and the game they wish they knew sooner.

 

Together, they unpack the highs, the lows, and the pivots in life, career, and relationships — so you either don’t have to go through it, or can move smarter when you do.

 

Every episode delivers real talk, hard-won insight, and practical gems to help you grow into the version of yourself that knows better… and does better.

You can&rsquo;t rewrite the past &mdash; but you can learn from it. Amber Grimes did exactly that, going from college dropout to Executive Vice President in the entertainment industry with no map, just mistakes and lessons that turned into power moves.
&nbsp;
If You Knew Better is where Amber shares that wisdom &mdash; alongside artists, creatives, and culture-shifters who open up about the missteps they made, the mindsets that changed everything, and the game they wish they knew sooner.
&nbsp;
Together, they unpack the highs, the lows, and the pivots in life, career, and relationships &mdash; so you either don&rsquo;t have to go through it, or can move smarter when you do.
&nbsp;
Every episode delivers real talk, hard-won insight, and practical gems to help you grow into the version of yourself that knows better&hellip; and does better.

If You Knew Better with Amber Grimes

Gail Bean Knows Defensive Dating

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/ad48064e-c4ce-4416-80ea-b4b100c5f680/transcript