Dating Red Flags: Cray—The App That Could Save Your HeartDating Red Flags: Cray—The App That Could Save Your Heart
Anonymous Andrew
Anonymous Andrew talks with app creator Justin Smith about Cray, a dating safety tool built from Justin’s own experience of extreme betrayal and trauma. They discuss red flags, love bombing, online scams, and how structured questions can help people—especially those over 50—protect their hearts and make safer relationship choices.
1:03:21•29 Jun 2026
Dating Red Flags and the Cray App: Protecting Your Heart Over 50
Episode Overview
- Betrayal and severe heartbreak can trigger serious physical and psychological trauma, and seeking intensive help can be a crucial step in recovery.
- The Cray app uses structured questions to highlight red flags and manipulative patterns, giving clear guidance like whether to stay, question, or leave.
- Love bombing, ignoring your gut, and dismissing early signs of disrespect or indifference are common ways people overlook dangerous behaviour.
- Older daters re-entering the scene after divorce or loss face new forms of online deception and can benefit from tools that flag romance and money scams.
- Privacy and safety are central: Cray keeps assessments on the user’s device, aiming to support even those who may be in controlling or abusive relationships.
“"List me out all 78 red flags that you know off the top of your head."”
What are the common struggles and victories in addiction recovery-style dating, especially later in life? This conversation on **Digital Dating Over 50** leans hard into emotional safety, manipulation, and the patterns that keep people stuck in painful relationships. Host Anonymous Andrew chats with Justin Smith, creator of Cray, a "self-improvement dating safety app" aimed at helping people spot red flags and avoid dangerous partners.
Justin shares his shattering story of betrayal: a long-term partner who secretly moved tens of thousands of dollars, pushed to get the house in her name, and left just after his major spinal surgery. The shock trauma was so intense he says, "I went and checked myself into one of the top trauma treatment centres in the U.S. for 60 days to recover." Out of that breakdown came the Cray app.
Justin explains the **Cray Score** for general red flags and the **Schemer Score** for manipulation and deception, including financial schemes and romance scams. Users answer detailed behaviour questions and receive a report with a score and plain-language recommendations like "run away" or "consider leaving." Andrew road-tests the app on a recent date and is stunned when it correctly flags someone who was stringing him along as a "severe risk" schemer.
The two men also talk about love bombing, cognitive dissonance, and why even intelligent, experienced people miss obvious warnings when they’re lonely, traumatised or dazzled by beauty. Justin stresses that Cray is private, designed so even someone in an abusive situation can quietly seek clarity and support.
If you’re over 50, coming out of a breakup, or rebuilding after trauma and addiction, you’ll hear both caution and hope: you can protect your heart, learn from the past, and still date with your eyes open. Could a simple set of honest questions save you months—or years—of pain?
Do you want to link to this podcast?
Get the buttons here!
More From This Show
The latest episodes from the same podcast.