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What happens when airline industry insights collide with modern dating adventures? In this candid conversation, Chris welcomes Lex from the Sidebar Pod to share her journey through both professional challenges and romantic explorations in Hawaii.
Lex pulls back the curtain on her seven-year career with Hawaiian Airlines, from her beginnings as a guest service agent to her current management role. Her stories range from hilarious to jaw-dropping—including an unforgettable encounter with an irate passenger who called her the C-word during a flight diversion crisis. Even more impressive is her dedication to advancement, once commuting daily between islands for three months straight just to secure a full-time position.
The conversation shifts to the battlefield of modern dating, where Lex describes the frustration of app-based connections that rarely materialize into real meetings. "I'm 30, I don't want a pen pal," she confesses, echoing the sentiments of many singles navigating digital romance in 2025. Her entertaining story about being recognized from TikTok at a sports bar demonstrates that sometimes the most promising connections still happen organically.
Both hosts open up about their therapy journeys, discussing how professional support has improved their communication skills and self-awareness. Their honest dialogue normalizes mental health conversations while highlighting how therapy can enhance relationship capability—whether with romantic partners, roommates, or family members.
Throughout the episode, Lex shares insights on adapting to island life as a Seattle transplant, maintaining her sports loyalties while embracing Hawaiian culture, and finding community in new places. The pair wrap up with a playful exploration of where to meet potential partners in everyday settings, from Target's home goods section to Costco's notorious free sample stations.
Join us for this authentic, humor-filled conversation that weaves together professional growth, dating adventures, and the universal search for connection. Whether you're navigating career challenges, swiping through dating apps, or considering therapy, this episode offers both practical wisdom and the comforting reminder that you're not alone in your journey.

• Working as a manager for Hawaiian Airlines and dealing with difficult passengers including one who used the C-word
• The logistics of commuting between islands for work, including a period when Lex flew daily from Honolulu to Maui
• Dating app experiences and the challenge of moving from online matching to real-life meetings
• How organic meetings can sometimes lead to more meaningful connections than dating apps
• The benefits of therapy and personal growth for improving communication skills
• Living with roommates versus enjoying the freedom of living alone
• Navigating life in Hawaii as a transplant from Seattle
• Potential places to meet people organically in everyday settings like Target and Costco
Follow Lex on Instagram and TikTok, and check out the Sidebar Pod for more entertaining conversations.