Host Jessie Sage sits down with Gem DeMilo for a heartfelt discussion about redefining fulfillment beyond romantic partnerships. Gem opens up about her solo journeys to Mexico City and Iceland, sharing how travel has deepened her life’s meaning and enriched her sense of self. Together, they explore the importance of close friendships, the unique joys of single life, and the ways society’s expectations can often obscure personal happiness. Gem emphasizes that her connections with friends and her beloved pet have brought her profound love and contentment.
Their conversation also delves into the challenges and misconceptions surrounding polyamory, as well as the critical role financial independence plays for women. Gem shares insights from her path of healing past relationship traumas, finding empowerment in being single, and reclaiming her self-worth beyond societal standards. The episode wraps up with Gem’s excitement for her upcoming 40th birthday celebration in New Orleans, and her commitment to financial literacy as a tool of empowerment for herself and others.
In This Episode:
00:01: Introduction to When We’re Not Hustling Podcast
02:44: Updates & Upcoming Events
05:20: Announcement of Collaboration with Tryst
07:52: Introduction of Guest Gem DeMilo
09:08: Gem DeMilo Discusses Being Single
17:20: Gem’s Life Changes & Moving to North Carolina
21:31: Finding Love & Fulfillment Outside of Relationships
32:25: Discussion on Solo Poly & Single Life
42:34: Reflections on Self-Worth & Letting Go
54:44: Conclusion & Excitement for Future Plans
Guest:
Gem DeMilo is a North Carolina based escort, originally from Chicago. She got her start in sex work back in 2009 working for a commercial dungeon as she worked on her MFA in creative writing. She quickly transitioned to sugaring, and transitioned to escorting quickly from there. In her spare time, she enjoys reading, writing, traveling, barre and volunteering with animals. She often snuggles with her feline son and soulmate, Jean-Claude.
You can find Gem:
Website: professordemilo.com
Instagram: @shesageminnc
Recommendations:
The Financial Feminist by Tori Dunlap
Girls Just Wanna Have Funds by Camilla Falkenberg, Emma Due Bitz and Anna-Sophie Hartvigsen
Important Note:
This episode was recorded prior to Hurricane Helene. Gem, who lives in Western North Carolina, would like to highlight several charities providing essential relief to Asheville and nearby communities.
The Rest:
Host: Jessie Sage
Producer: Emily Foster
Music: Benjamin J Benamati
Sponsor: Assembly Four
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