Flipping Tables – Episode 47: "Important Conversations with Anna Connelly"
Host: Monte Mader
Guest: Anna Connelly
Release Date: December 23, 2025
Episode Overview
In this candid and insightful episode, Monte Mader sits down with viral content creator Anna Connelly to discuss the accessibility of difficult conversations around progressive issues—especially as we head into the holiday season when families with divided beliefs often gather. Monte, herself a former alt-right evangelical, and Anna, known for her humorous and direct online skits, dig into the practicalities, pitfalls, and strategies for having real, change-making conversations on topics ranging from race and generational wealth to women’s health and white privilege. The episode is a toolbox for anyone feeling overwhelmed by the polarization in America, wanting to bridge divides with curiosity, honesty, and heart.
Key Discussion Points and Insights
1. Anna’s Background & Rise to Platform
[02:32-03:35]
- Anna shares that she began posting only in April, starting on TikTok out of frustration with the negativity and echo chambers online.
- Her upbringing in a blend of science-focused and rural communities (Minneapolis/Rochester/Bemidji, MN) allows her to speak to and understand both sides of polarizing issues.
"I just wanted to give people the words to use in those conversations." – Anna [04:36]
Notable Moment
Anna reflects on never unfollowing people with opposing views, valuing seeing "what's really being posted" for awareness and authentic response. [06:47]
2. Using Social Media to Foster Real Dialogue
[06:37-08:29]
- Both Monte and Anna stress the necessity of remaining exposed to differing viewpoints to understand what drives misinformation and divisive rhetoric.
- Anna doesn’t cut out those from her past who post content she disagrees with, maintaining a view into perspectives outside her current ideology.
"Otherwise I'm in the dark... we get further and further into these echo chambers and misinformation gets spread so quickly." – Monte [08:29]
3. Firsthand Reflections on Minneapolis/BLM Protests
[09:18-11:54]
- Anna recalls moving near the epicenter of the George Floyd protests, describing the surrealism of military tanks in the streets, ash from fires, but also immense local pride and community action.
- Both hosts highlight how right-wing narratives often miss the crucial context of external agitators influencing violence during protests.
"You would see [white nationalists] driving around in cars and like tanks... It was crazy. So truly felt like the apocalypse. But...I'm so proud of Minneapolis." – Anna [09:46]
4. Race, Identity, and Choosing Discussion Topics
[12:36-14:55]
- Anna, from a blended and racially diverse family, is "passionate about race issues" and finds that moving from racially diverse areas to much whiter Minnesota sharpened her awareness of white privilege and resistance to recognizing it.
"Opening up their eyes to this and opening up their eyes to the white privilege, they get mad hearing it because they're like, I don't have that privilege." – Anna [14:23]
5. Women’s Health and Reproductive Rights
[14:55-19:10]
- Both share frustrations with cultural ignorance about women's health, noting lack of education and the dangerous rhetoric stemming from Christian nationalism.
- Anna shares memories of abortion protests targeting women pursuing "medically necessary" terminations, expressing outrage at the lack of empathy and broader pro-life hypocrisy.
"Nothing enrages me more than that...these people are coming in to have the worst day of their lives. And you're doing this right now." – Anna [18:32]
- Monte comments on the dishonesty within some pro-life circles and the disconnect between espoused values and policy support.
"Pro choice people are actually pro life because they support everyone's life in the conversation." – Monte [21:11]
6. White Privilege & Generational Wealth – Strategies for Conversation
[22:35-28:28]
- Anna details her approach to discussing white privilege, favoring asking questions over direct confrontation.
- She references her popular skit visualizing generational wealth disparities from the Civil War to now, outlining how systemic exclusion from education and home ownership perpetuates inequality.
"If you're...able to even have the tiniest bit of money and they passed down land and nothing else, you're already ahead. Whereas, you know, a Black person didn't have that opportunity because they couldn't own it." – Anna [26:20]
- Both emphasize that data and history are tools to plant seeds of doubt, rather than win arguments outright.
7. The Limits and Power of Social Media Activism
[29:11-37:13]
- Anna expresses anxiety about left-wing “purity testing,” where progress is stifled by demands for ideological perfection, particularly among younger activists. She warns that refusing incremental change leaves marginalized groups more vulnerable.
"If you haven't had to face that and you just say, I want all of it right now...you also have the privilege of not being affected when they say, we're not going to give you anything. And so people say...I'm not going to vote. But other people are impacted by this." – Anna [30:01]
-
Monte draws a medical triage analogy, urging listeners to prioritize urgent issues over exhaustive ideological points.
-
Both caution that social media encourages believing “calling out” creators equals activism, while real-world action is needed.
"I think a lot of people think that their activism is messaging creators and just like shaming on it." – Anna [35:25]
8. Staying Rooted, Resilient, and Hopeful
[37:38-43:45]
- Anna receives daily affirmations from her audience, which she says demonstrates that there is a large, engaged progressive community.
- She urges listeners to remember that "a lot is happening under the surface"—important progress work that may not be headline news.
"What gives me hope is my platform growth...There are so many of us." – Anna [40:43]
- Monte finds hope in the fact that America has faced similar crises and regressive movements before and that "showing up consistently" leads to change.
9. Practical Tools for Difficult Conversations
[44:53-49:27]
Anna’s Communication Model: THINK-FEEL-DO
- Think: What do you want them to think?
- Feel: How do you want them to feel?
- Do: What do you want them to do afterward?
- Set intention before conversation; don’t aim to “win” but to plant seeds of doubt or gently nudge beliefs.
"If I can get the tiniest little seed of doubt, that is a win for me. And I walk away and I'm like, yes, did it." – Anna [48:00]
Approach with Questions
- Use questions to lead others to their own conclusions rather than confront or “fix” them outright.
- Data: Useful, but only if the person is open. Questions are better with entrenched beliefs.
"Asking the questions and leading them to their own right...is so much more powerful than me yelling at them and saying, you're wrong." – Anna [46:07]
Set Boundaries
- If conversations are dangerous or escalate to aggression, it’s okay to set or walk away from the boundary.
"If you're talking to someone who is vitriolic, violent, aggressive, don't. Just don't." – Monte [49:27]
10. Realistic Encouragement for Holiday Conversations
[54:46-56:43]
- Prepare: Set the stage, state your intention (openness, love, curiosity) to the person before launching in.
"You can even do the think, feel, do as, like, tell them that here's what I want you to think and feel, and I want you to know that I love you and...I really don't want this to be a conversation where we both leave feeling horrible. Can you agree to that?" – Anna [54:46]
- Start Small: Sometimes progress is just saying, “I don’t agree with that” or calmly setting a boundary.
- Practice: The more you have these conversations, the easier and more effective they become.
Notable Quotes & Moments
- On the pitfalls of online purity:
- "Otherwise we're not going to move at all. So that's my biggest concern right now...Gen Z does not understand...you're not going to get 100%." – Anna [29:11]
- On hope and solidarity:
- "We have been here before...showing up consistently leads to change." – Monte [42:07]
- "There are so many of us." – Anna [40:43]
Fun & Personal Section
Anna’s Comfort Picks (Movies)
[58:16-60:01]
- Palm Springs
- Never Been Kissed
- Wicked (new)
Advice on Living Well
[61:48-62:58]
"A good life to me... I want, like a legacy of Anna stood up for the right things...but I want to be able to create change and have these conversations in a way where I don't have to change myself...being just authentic is so important to me...that's probably like the good life." – Anna
Important Timestamps
- 02:32 — Anna’s background, start of her online presence
- 09:18 — Anna’s firsthand experience in Minneapolis during George Floyd protests
- 21:11 — Critique of pro-life rhetoric
- 25:34 — Anna describes systemic racism, generational wealth video
- 29:11 — Concerns about progressives and purity testing
- 40:43 — Anna on finding hope, seeing progress
- 44:53 — Anna’s THINK-FEEL-DO model for conversations
- 54:46 — Encouragement, practical tips for holiday discussions
- 61:48 — Defining a good life/authenticity
Final Thoughts
Anna and Monte’s conversation demystifies the art of having “important conversations.” The episode is suffused with humor, realism, and empathy. Listeners are encouraged to show up—with their hearts, with questions, and with boundaries—especially during tense times. Change doesn’t require expertise or perfection, just willingness, curiosity, and the courage to stay engaged.
Find Anna:
@annaconnellyiscool on Instagram, Facebook, TikTok
Listen Next:
Flipping Tables – new episodes weekly with Monte Mader