Should You Date Him When He’s Struggling?

Have you ever wondered if you should date a man who’s struggling? In this special 400th episode of the Love U Podcast, I reflect on my own darkest seasons and share why timing—not just chemistry or potential—can make or break a relationship. You’ll hear vulnerable stories, hard-earned insights, and a powerful truth: you can’t build a future with a man who isn’t emotionally ready right now. I’ll also explain why empathy doesn’t mean you have to sign up to be someone’s therapist, savior, or safety net. If you’ve ever dated a man based on who he could be instead of who he is, this episode will shift your perspective. Tune in now—this one could save you years.

What You’ll Hear:

• Celebrating 400 episodes of the Love U Podcast and 3 million+ listens across 220 countries

• Evan shares behind-the-scenes evolution of the show since 2016

• The most popular episode of all time (featuring Lori Gottlieb)

• Personal stories of being passed over in dating due to career struggles

• Why timing, stability, and emotional readiness matter more than potential

• Hard truths about dating someone who’s struggling — and how to protect your future

• Advice on recognizing high-risk relationships and avoiding self-sacrificing patterns

Full Episode Transcript
Hey, this is Evan Mark Katz, dating and relationship coach for smart, strong, successful women, your personal trainer for love. Welcome back to the Love You Podcast. It is a very special episode because as far as I can tell this is the 400th episode of the Love You Podcast.

400 individual episodes will be in the can as of today and that’s a milestone. Over the years I had a blog that you know used to get 12 million readers in a year. We had over a thousand blog posts on that.

Then the internet moved to podcasting. I started