In this episode of If You Knew Better, Amber Grimes sits down with Justice Baiden for an honest conversation about relationships, purpose, and the lessons that come from committing before you're truly ready [00:00]. Justice explains why he initially avoided serious commitment [01:05] and reflects on how early success in the music industry changed the dynamics of his relationships [05:24], ultimately teaching him the importance of establishing purpose before partnership [07:49]. He opens up about avoiding difficult conversations in an effort to "keep the peace" [09:59], ignoring red flags while convincing himself everything was working [14:02], and expressing love by trying to fix problems for his partner [16:50]. Justice also examines how unspoken resentment and passive-aggressive communication eventually manifested as stress [18:19], leading him to recognize that healthy relationships require clarity about individual goals [22:24], reconnecting with the passions and interests that once gave you direction [24:34], and creating intentional next steps toward the life you actually want [25:46].

Justice goes deeper into why actions ultimately matter more than promises [27:59] and introduces the importance of defining "yours, mine, and ours" within a partnership [28:37], including honest conversations about sacrifice, expectations, values, and true non-negotiables [30:34]. He reflects on overcoming the fear, guilt, and concern about other people's perceptions that can keep someone trapped in an unhealthy relationship [33:27], while confronting remorse, infidelity, and the responsibility of breaking destructive patterns [35:46]. The conversation also explores how father figures and role models shaped his understanding of manhood and relationships [40:51], the healing that can come from reparenting yourself through honest conversations [42:29], and the biggest lessons he carries from past love [44:12]. Now with a clearer understanding of himself, Justice shares whether he's ready for love today [45:54], before closing with a powerful reminder that lasting relationships begin with transparency, self-awareness, purpose, and the courage to tell the truth—even when that truth is uncomfortable [50:19].

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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].

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In this episode of If You Knew Better, Amber Grimes sits down with singer-songwriter Naomi Sharon for a vulnerable conversation about childhood trauma, anxiety, rumination, and how unresolved experiences can follow us into adult relationships. Naomi sets the tone by opening up about her mental health journey [00:00] and explains how anxiety can turn into cycles of overthinking and rumination [00:53]. She traces many of those patterns back to her parents’ difficult divorce when she was 12 and the relationship triggers that developed from it [03:11], including fears around secrets, hidden truths, and a desire for radical honesty that can become its own emotional loop [04:49]. Naomi discusses building a greater tolerance for emotional discomfort instead of constantly searching for immediate peace [08:09], discovering relationship OCD and recognizing herself in its patterns [09:41], and learning how safety, self-awareness, and healthier coping mechanisms can interrupt behaviors rooted in childhood survival [13:31]. She also reflects on gratitude and transforming pain into art [20:16], balancing mental health with the demands of her music career [23:28], and how her parents’ divorce continues to shape her private life and family relationships [26:29], including hearing her brother’s perspective and confronting the absence of her father [27:00].

The conversation deepens as Naomi explores therapy and the process of finally meeting the younger version of herself who carried responsibilities far beyond her years [30:25]. She discusses learning to let difficult feelings exist without immediately trying to fix them [30:52], reparenting and comforting her inner child [31:26], and what she would tell her 12-year-old self today [33:07], leading to an emotional breakthrough symbolized by a powerful teddy bear story that Amber shares [33:41] and the release that comes from allowing herself to cry [37:25]. Amber and Naomi also explore choosing partners who create emotional safety, understanding different love languages [40:47], and the importance of centering yourself as you enter a new stage of adulthood [45:09]. Amber reframes ego as something that can be adjusted [46:34], reflects on discovering who she is when she's truly alone [49:22], and considers what real love looks like when two people continue changing and growing [52:38]. She closes by discussing the freedom of sharing her authentic self [54:05] and reflecting on a healing journey built around self-compassion, emotional honesty, and learning to give herself the safety she once searched for in others [55:36].

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In this episode of If You Knew Better, Amber Grimes challenges women to rethink modern dating by throwing away rigid relationship checklists in favor of 5 non-negotiables that prioritize character, compatibility, and emotional safety. Amber opens by inviting listeners to question their dating "type" [00:00] before explaining why it's time to let go of limiting checklists [01:13] and how that mindset shift transformed her own love story [03:14]. She reveals why attraction often grows through emotional connection rather than first impressions [04:56], explores the idea that many people know more about what they don't want than what they truly need [08:44], and introduces a practical framework for building healthier relationships through five intentional relationship buckets [10:33]. Amber then breaks down the first four non-negotiables—safety [12:16], communication and emotional availability [14:18], shared values [17:06], and future lifestyle alignment [19:33].

The conversation concludes by encouraging listeners to identify one authentic deal-breaker instead of an endless list of preferences [22:34], expand their dating pool by casting a wider net [24:22], and approach dating with greater intention through meaningful conversations rather than surface-level attraction [27:00]. Amber also reminds listeners that healthy relationships are built on mutual choice—not chasing someone who doesn't choose you back [30:56]—before leaving the audience with a practical exercise to redefine their approach to love [31:43]. Combining actionable dating advice, self-reflection, and relationship wisdom, this episode offers a refreshing roadmap for anyone ready to build stronger, healthier, and more intentional connections.

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In this episode of If You Knew Better, Amber Grimes sits down with Algee Smith for a thoughtful conversation about identity, purpose, and finding self-worth beyond success. Algee reflects on how social media and career milestones can become unhealthy measures of personal value [00:27], revisiting the breakthrough role that changed his life with The New Edition Story [01:08] and the lessons he learned about detaching his identity from achievements [03:00]. He opens up about career disappointments that once felt devastating [04:58], how faith helped him embrace the belief that delay is not denial [06:55], and the daily practices—including prayer, stretching, meditation, and journaling—that have grounded him through seasons of uncertainty [09:08] [10:31]. Algee also discusses balancing authenticity on social media [12:50] while protecting the parts of life that deserve privacy [15:27].

The conversation deepens as Algee shares how therapy transformed his perspective despite his initial skepticism [16:28], helping him uncover childhood experiences [19:02] that fueled a lifelong search for validation [20:08] and shaped his ambition through unresolved trauma [21:08]. He explains his philosophy of "winning the day" by focusing on daily habits instead of distant outcomes [22:37], embracing the process [24:44], and valuing skill development over raw talent [26:34]. Closing the episode, Algee previews his upcoming EP, television pilot, film projects, and producing ventures [27:57], offers advice to his younger self [29:41], and reflects on the growth that has made him most proud [30:41]. Honest, inspiring, and deeply reflective, this episode offers practical wisdom on healing, discipline, purpose, and defining success from the inside out.

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In this episode of If You Knew Better, Amber Grimes sits down with sports journalist Jemele Hill for an honest conversation about love, marriage, and building a partnership on your own terms. Jemele shares why she defines marriage as a daily commitment rather than a destination [01:04], reflecting on how years of prioritizing her career [03:03] and lessons from her family [03:23] initially made marriage feel unlikely. She opens up about meeting her husband [07:40], embracing a relationship without rigid expectations [09:05], and how a long-distance romance built on consistency, intention, and clear communication laid the foundation for their future together [11:42]. Jemele also recalls making their relationship public [14:53], explains the importance of "minding your business" instead of letting outside opinions dictate your relationship [17:06], and challenges common misconceptions about dating, marriage, and Black women's desirability.

The conversation expands into the role money, ambition, and shared values play in healthy relationships, as Jemele discusses financial compatibility [22:42], redefining standards beyond salary [26:01], and the humorous story behind her "Amex glow up" [26:29]. She explains why unwavering career support from a partner matters [28:00], how marriage has increased accountability and encouraged greater vulnerability [29:44] [34:35], and why true emotional safety allows her to embrace a softer side of herself [37:07]. Closing the conversation, Jemele offers practical dating advice [41:49], shares her perspective on choosing marriage without feeling pressured by timelines around children [46:04], reflects on navigating a new season of professional transition [49:45], and wraps by discussing her latest book and what's next [53:16]. Thoughtful, empowering, and deeply personal, this episode offers a refreshing perspective on relationships, success, and defining happiness on your own terms.

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In this episode of If You Knew Better, Amber Grimes sits down with Lil Rel Howery for an inspiring conversation about building a lasting career in entertainment through persistence, purpose, and creative evolution. Rel reflects on the moment he realized he'd truly "made it" in film and television [00:46], then looks back to the high school performance that first showed him he could win over even the toughest audiences [02:04]. He shares how directing became part of his journey after encouragement from Bobcat Goldthwait [03:29], the lessons he learned making his directorial debut [06:19], why collaborating closely with every department shaped the experience, and how casting friends and fellow comedians—including support from Tiffany Haddish—helped bring his vision to life [07:56]. The conversation also explores his love of horror-comedy [11:00], how comedy continues to evolve alongside audiences [13:46], and the way grief and personal experiences have informed both his work and perspective [16:47].

Rel also discusses the importance of inspiring the next generation to understand the many career paths available in entertainment [19:10], the values instilled by his parents through community service and mentorship [22:46], and the filmmakers who inspired his own creative ambitions, from Steven Spielberg [27:08] to the lessons he drew from Sylvester Stallone and Rocky [29:04]. He explains why studying the business has been just as important as mastering the craft [30:37], the unique challenge of acting while directing [32:34], and how he now defines success through personal milestones like Get Out and his Chicago Theatre special [33:54] [36:36]. Closing on a reflective note, Rel shares how he stays grounded and present [43:53], the wisdom and healing that have shaped this stage of his life [47:07], and previews his new horror-comedy Haunted Heist, arriving in theaters on July 24 [50:50].

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In this special episode of If You Knew Better, Amber Grimes shares the biggest personal announcement of her life—she's expecting her first child. Amber opens the episode with her exciting pregnancy reveal [00:00], explains why she waited to share the news publicly [01:59], and reflects on manifesting the space to embrace motherhood through maternity leave [03:52]. She also recounts the encouraging conversation in Las Vegas that shifted her mindset [05:22], the emotional moment she took the pregnancy test [06:41], and the unforgettable surprise of telling Conor they were expecting [08:59]. Amber candidly discusses keeping the pregnancy private [11:16], navigating first-trimester exhaustion [11:50], and adjusting to new routines centered around nutrition, hydration, and prenatal care [14:04].

As the journey continues, Amber shares the emotional experience of telling family at 12 weeks [17:32], explains why she chose to skip a traditional gender reveal [19:13], and instead joyfully reveals the gender on the show [19:54]. Looking ahead, she invites listeners to be part of this next chapter [21:02], laughs about baby names and maternity fashion [23:17], and closes with heartfelt reflections on gratitude, growth, and the life-changing adventure of becoming a mother [24:02]. Filled with vulnerability, excitement, and optimism, this episode marks the beginning of a deeply personal new season and celebrates the power of embracing life's biggest milestones.

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