Widower Wednesday: 5 Dating a Widower Questions

Just a reminder to anyone who wants their dating a widower story to be considered in my upcoming Dating a Widower book, you have until May 13 to submit a story. I’ve received a bunch of great entries so far and think that your additions will really take this book to the next level. I’ve read through all of them so far and will be making final decisions before June.


Sometimes I get some dating a widower questions that can be answered in just a couple of sentences. I feel they’re too short for one Widower Wednesday post so I’ve decided to combine five of them into one post.

Q: My widower wants me to go on a weeklong vacation with him and the late wife’s parents. Should I go?

A: That really depends on if you think a vacation like that will hurt or help your relationship. If you get alone with the LWs parents and the widower does a good job of treating you like number one, then I don’t see a problem with it. However, if you feel like you’re going to be an uncomfortable or miserable time, or that you won’t enjoy the trip for any reason, don’t go. There’s no point in torturing yourself for seven days. Wish them all a good time and enjoy some time to yourself while they’re gone.

Q: Will a widower who breaks off a relationship come back after he’s had time to grieve and heal?

A: Probably not. Men have an amazing ability to overcome their grief when the right woman comes along. If he wasn’t able to make room in his heart for you now, odds are he won’t be able to do it after some away to grieve. Waiting around is going to lead to more heartbreak. I recommend moving on.

Q: The widower I love is involved in a lot of self destructive behavior (drinking, drugs, and gambling). What I can do to help him?

A: It’s sad when people chose to destroy their lives. However, there’s nothing you can do to make them stop. Usually people have to hit bottom or have something happen to them before they decide to change their lives for the better. The only thing you can do is offer them an alternative to their activities (e.g., a movie and dinner instead of a night at a bar or casino) and hope they want to be with you. Keep in mind that getting involved in the lives of people who are destroying themselves often end up getting hurt physically, financially, and/or emotionally.  I’d hesitate to get to close to anyone with these problems until they’ve done some serious rehab.

Q: I’m dating a widower who is also an artist and has several paintings of the LW in their home. He refuses to take them down because he says they’re some of his favorite work. What can I do to convince him to take them down?

A: I don’t think there’s much you can do. It’s his home and he can put whatever he wants on the walls. IMHO his actions are stating that he values the paintings more than your feelings. If you can’t live with the paintings on the walls and he doesn’t want to take them down, there doesn’t seem much point in continuing the relationship.

Q:  I’ve found your blog very helpful but there’s one issue you haven’t addressed. There’s a 22 year age difference between me (23) and my widower (45). Do you think our age will make a difference whether or not things will work out?

A: I think if two people are in love, age doesn’t matter. However, I do find older men (widowed or not) who date women young enough to be their daughters a bit creepy. You might want to really examine the relationship and make sure it’s fueled by love.