S2 Episode 33: We Hoped Dating After Widowhood Would Be Easier (Part 2)

Guest note: Our guest requested anonymity. We refer to them as Lee throughout. Episode Description In Part 2 of our dating series, Amy and Cheryl continue our sit down with Lee, a therapist and widow, who takes us behind the scenes of midlife online dating: the hope, the gut checks, and hard boundaries. We talk about AI-polished profiles, spotting scams, healing after heartbreak, and what it looks like to "choose yourself" first. This conversation is tender, honest, and surprisingly funny, because sometimes the best way through a rollercoaster is to laugh, take notes, and keep your friends on speed dial. Guest Introduction Lee is a licensed counselor and thoughtful truth‑teller who recently spent six months exploring online dating after widowhood. With equal parts compassion and curiosity, she shares both her personal experiences and professional perspective on what helps, and what hurts, when you’re ready to connect again. Key Topics & Takeaways AI & authenticity online: Profiles can read like travel ads, overly polished, tidy “lists of three,” and wording that doesn’t match the person’s real-time messages. Trust the mismatch; it’s data. Spotting scams & red flags: Look for formulaic language, over-religious signaling like “seeking a God-fearing woman,” and writing that feels generic or too perfect. Photos are often stolen; the writing is the tell. “Choose yourself” first: You can’t genuinely choose a partner until you’ve chosen yourself, liked yourself, backed yourself, and named your non‑negotiables. Dating takes work: For Lee, six months of dating across four platforms felt like a part-time job, time-consuming and not cheap. Effort in doesn’t always equal effort back. Hold the opposites: Take dating seriously and stay light-hearted. Hope for connection and release attachment to outcomes. Be invested and okay if it’s not forever. Boundaries are kindness: Protect your peace fiercely. Clarity about what you want, and what you won’t do, saves time, money, and heartache. Resilience after loss: Healing isn’t linear. A painful discovery set Lee back for a while; honesty (with herself and others) helped her recalibrate. Where Lee is now: Enjoying a high‑quality connection that’s currently limited by travel and availability, and taking a break from paid apps while life sorts itself out. Memorable Lines “You can’t choose someone else without first choosing yourself.” “Dating was a part‑time job for six months.” “Protect yourself fiercely. Be on your own side.” “A good relationship makes the hard things softer and the good things better.” “Can you hold out hope and let go of attachment to an outcome?” “Have dinner with your girlfriends and tell them all your crazy stories.” Connect with Us If today’s episode landed for you: Subscribe & Review on your favorite podcast app Share this episode with a friend who’s dipping a toe back into dating. Join us on Instagram and Facebook @ThisWasSupposedToBeEasy for weekly prompts and behind‑the‑scenes. — Amy & Cheryl