Starting over at 50 can feel like the end — especially after losing your business, your marriage, your money, and your sense of self-worth.

In this episode of Dating to Win, I share a powerful message inspired by a real letter from a Gen X man who lost everything after COVID and is now rebuilding his life from rock bottom.

We talk about: • What it really means to lose everything as a man • Why Generation X was hit harder than most people realize • How to rebuild confidence after failure and divorce • The mindset shift from victim to survivor • How to approach modern dating when you’re starting over • Why character matters more than money later in life

This isn’t hype or toxic positivity. It’s real talk for men and women navigating modern dating, rebuilding their lives, and learning how to start over with clarity and purpose.

If you feel written off, invisible, or behind in life — this episode is for you.

🎧 Subscribe to Dating to Win for modern dating advice, confidence-building conversations, and honest relationship guidance.

📩 Contact: advicefordating00@gmail.com

Youtube.com/@DatingtoWin25

Episode Description

Is your phone the third wheel in your relationship? In this episode of Dating to Win, we dive deep into the silent killer of modern romance: social media. From "digital jealousy" to the endless comparison trap, we explore how likes, comments, and DMs are creating cracks in even the strongest foundations.

We’re not just ranting—we’re giving you the playbook on how to social-proof your love life in 2025. Learn the signs of social media addiction, how to set healthy boundaries, and why keeping some things private might be the secret to lasting intimacy.

In This Episode, We Cover:

• [0:00] Intro: Why we swipe more than we speak.
• [02:06] The Comparison Trap: Why their "highlight reel" makes your real life feel inadequate.
• [04:10] Digital Jealousy: How to handle the anxiety of "who is he/she following?"
• [05:00] Micro-Cheating: When does a DM cross the line?
• [06:07] The Fix: Practical boundaries to reclaim your connection.

Connect with Dating to Win:

• YouTube:Dating to Win on YouTube
• Email : AdviceforDating00@gmail.com

Thinking about getting back together with an ex? In this episode, we tackle the controversial question: Should You Take Your Ex Back?

If you are navigating the chaos of modern dating and wondering "is it worth it?", this Q&A session provides the brutal relationship advice you need before you send that text. We dive deep into the realities of dating in 2025 to help you make the right choice for your future.

In this episode, we cover:

• The psychology behind why we want our exes back
• How to spot red flags before you recommit
• The honest truth about self-improvement after a split
• Practical first date tips for when you're ready to move on
• Answering viewer emails on: "Why am I single?" and finding love again

Whether you are looking for dating advice for men or women, this episode covers the essential tips to stop you from repeating past mistakes.

Timestamps:

[00:00] Intro: The hardest part of dating today

[01:30] Should you take your ex back? (The Brutal Truth) [04:45] Why you feel like asking "why am i single"

[04:20] How to build healthy relationships moving forward

[07:15] Modern dating Q&A: Viewer emails answered