When Dating Doesn’t Work for 17 Years | Deena and Kalman Flaks | Stories of Hope

In this deeply honest episode, Deena Flaks and Kalman Flaks share their raw, unfiltered journeys through years of dating, heartbreak, faith, doubt, and resilience—before finally finding each other later in life.Deena opens up about dating from 19 to 36, going out with over 200 people, navigating pressure, intuition, burnout, and the quiet fear of “maybe something is wrong with me.” Kalman shares his path through community leadership, divorce, public scrutiny, choosing joy, and continuing to build others even when life didn’t go according to plan.Together, they speak candidly about singlehood, delayed marriage, trust in Hashem, emotional clarity, red flags vs. intuition, the damage of gossip, and what actually matters when choosing a partner. This conversation is not about segulos or shortcuts—it’s about faith, patience, self-honesty, and believing you didn’t miss your moment.If you’re single, supporting someone who is, or carrying quiet doubts about your timeline, this episode will make you feel seen.Watch until the end for powerful advice for singles, parents, and anyone struggling with fear, comparison, or loss of hope.To contact Deena and Kalman Flaks:📧 [email protected] episode was made possible thanks to our sponsors:► PZ DealsDownload the app and never pay full price again!https://app.pz.deals/install/mpp _____________________► Colel Chabad Pushka AppThe easiest way to give Tzedakahttps://pushkapp.cc/meaningful_____________________► Chesed 24/7 — RUN 24.7Help keep Chesed rooms running in 30 hospitalsJoin the live 5K at American Dream Mall (Feb 22, 2026) or sign up as a raiser—every mile keeps the rooms going.https://run4chesed.org_____________________► B’Sefer ChayimWhen you get married—or marry off a child—you plan for the future. You make thoughtful choices. You lay the foundation for what comes next. Life insurance is one of the cheapest, simplest, smartest things you can do.Life insurance isn’t just a nice idea, it’s a basic.www.bseferchayim.org_____________________►Pizza BizaDelight your guests with our expansive menu and a culinary experience that exceeds expectations.https://www.pizzabiza.com