Dating a Widower: 4 Tips to Make It a Success


Well, for starters, a man who had a good, long marriage can be a great catch! He probably knows how to love, communicate, commit, work through problems and misses being married. When a man is in a happy relationship he pours himself into it. And when it’s gone, he’s left with the kids (maybe) and his job (maybe). That leaves a giant hole. So if he knows what he wants and is ready for love again, he takes his search for a new partner seriously – and that’s the gem of dating a widower.

Let’s be honest. We’re not 20 anymore. We’ve experienced a lot: love, heartbreak, successes, failures – and having lost a spouse is a very real possibility. But, as with all of those other big life experiences, being a widower isn’t the end of the story.

Should you pay attention to his emotional availability, and watch for red flags? His ability to be present? His life in the here and now? Absolutely, yes! But that’s the case with every man you date.

Look, here’s my best advice: know your must have’s, and go into every date looking for at least one thing that is RIGHT about him. If he makes you feel good, explore it further. But don’t rule him out just because of his scarlet W.

And whether by chance or by choice you do find yourself dating a widower, remember these 5 tips:

  1. Always remember it’s not a competition. She was an enormous part of his life. But that doesn’t mean you aren’t too. Be sure to talk about issues as they come up, how they make you feel, and how you can handle them as a team.
  2. Allow him to grieve during anniversaries and birthdays. Ask how he would like you to support him. Because he grieves for her doesn’t mean he cares for you any less.
  3. Ask him if he wants you to get to know her. You’re probably curious about her but allow him to share and express as he feels comfortable. It’ll probably also help you get to know him better.
  4. Don’t think you have to be anything like his wife! She’s not your competition.

Yes, it’s a flag if he talks about her constantly, but it can also just be a habit. If he does, let him know you understand though you’d like to get to know him. If he persists…he’s not ready.

If you’re in early dating, don’t hesitate to have a grownup, direct conversation about his readiness to feel deep connection with another woman. Then believe him, and pay attention to his actions. It is true that some think they are ready but not (just like after a breakup, right?).

Don’t assume any specific number of months or years is required until he’s ready. You don’t know the situation – maybe she was sick a long time which often means he’s ready to start new…learn his story, don’t make assumptions. Or you just may miss out on Mr. Right.