Is It a Red Flag If He Doesn't Tell You He's a Widower?

Note: You can watch a video version of this post here.

A viewer writes, “Abel, what if he doesn’t tell you he’s a widower on the first date?”

Personally, I’d hope he brings it up right away on the second date and has a good reason for not mentioning it sooner. Is it a red flag or a dealbreaker? Not necessarily. I’ve worked with clients in this situation, and as long as there’s complete honesty and transparency going forward, I’d usually let it slide.

To be fair, my first date with Julie probably would’ve gone better if I hadn’t dropped the “widower bomb” right in the middle of dinner. Waiting until the second date might have made things smoother. The bigger issue isn’t whether he tells you on date one or date two—it’s whether he’s emotionally ready for a real relationship.

So, whether he tells you on the first date or the second, keep your eyes wide open for red flags and make sure he’s truly ready to open his heart to you.