Widower Wednesday: How to Flirt with a Widower

From the inbox comes a question I’ve never been asked before:

I currently work with a man who lost his wife two years ago. We have a great professional relationship but I would like to date him and see if we could possibly become something more romantic and serious. I’ve talked to a friend about this who suggested its better if I let the widower pursues me instead of me asking him out. After reading through your blog posts I see that you agree with her. If it’s best to let the widower make the first moves, what can I do to let the widower know I’m interested in going out with him?



First, your friend gave you great advice. It’s usually best if men do the initial pursuing in a relationship but it’s doubly important when dating a widower. It may sound old-fashioned but widowers, especially recent widowers, have a difficult time committing to long-term relationships. Though they enjoy the benefits of a relationship (physical contact, sex, companionship, etc.) it can be hard for them to open their heart to someone else. When a widower has to take the initiative it forces him to decide whether or not he’s really ready to date again instead of enjoying the benefits of a relationship without having to work for it and decide if he’s ready to give you his heart.

So what can you do to let him know you’re interested in having more than a professional relationship? You can start with flirting to see if he responses. Something as simple as a special smile, casting a longing look, or engaging in witty banter may be all it takes for him to start flirting back. New clothes or a new hairstyle may also help the widower take notice. Another way is, when the opportunity presents itself, casually ask him about his life, interests, and hobbies and start building on things that you have in common (outside of work).

And though I’m a big advocate of men making doing the chasing, if flirting or subtle suggestions don’t work, you can always ask him out for coffee or a drink after work that can just give the two of you time to chat in a more casual environment. If he accepts, this will give you a chance to talk one-on-one, maybe flirt a little more openly, and get to know him better outside of work. That alone could loosen things him up and move things along.

Just keep in mind that no matter how much you’d like to move things to forward, the widower my simply not be ready for or interested in a relationship. Don’t take it personally if he rebuffs your advances.

The other complication to watch out for is how your flirting or dating (if it goes that far) could impact on your work, co-workers, or your professional reputation. I personally don’t have a problem with single co-workers flirting or even dating but it can lead to unforeseen a complications. It’s something to keep in the back of your mind as you move forward.

* Name changed