Dating a widow or widower is not necessarily just for people older than 60. Women in their 30s and 40s become widows every day due to accidents, or illness, etc. Since finding widows out in the dating world is really not all that uncommon, I thought I would put together a list of guidelines and things to think about if you are just starting to date a widow, or are simply contemplating whether to date a widow. There are definitely a number of issues to consider. Oh – and the flip side of all of this equally applies to women who may wish to date a widower.

1) Where is she in the grieving process?  Has she had the necessary time to properly grieve? Grieving must take place in order for her to move forward with her life … which includes new relationships. Some people grieve more quickly than others … which means for some, it might be a matter of months. Yet for others, it could take years. Give her the time she needs to heal, and don’t force a new relationship on her. If your relationship with her is right for her, then she’ll gravitate toward you naturally.

2) Be prepared to respect her previous relationship, and don’t insist on changing things (like taking down photos, or not wearing a ring, etc.) … at least not for a while. Give her the time she needs to work through it all, and process it. Respect her thoughts, respect her feelings … it is really all about respect on your part.

3) Be supportive (not jealous) – especially as emotional moments surface sometimes unexpectedly … including on special occasions such as birthdays or holidays. You cannot possibly imagine what she as a widow has gone through, so your best bet really is to be there for her no matter what the range of emotions or thoughts she has. You will get a lot more mileage out of being supportive versus anything else. And your relationship with her will wind up being that much stronger over time because she will know she can count on you to be in her corner, no matter what.

4) Watch for rebound behavior – filling an emotional void too quickly can lead to mistakes by all parties. Some people fear being single – and that fear can drive them into rebound behavior … which often means getting involved with someone who is not good for you in the long run. I’d guess that widows (or widowers) might be prime candidates for rebound behavior after he or she has gone through their grieving process. The message here is – just make sure that both of you are getting involved with one another for the right reasons. If you want to know more about rebound behavior, read the subsection here called Rebound – Does Fear of Being Single Drive Your Behavior in the section called Develop a Strategy for Midlife Bachelor Success under Midlife Dating Advice.

5) Know that she might not be ready for a relationship too soon.  She might just be looking for a friend, or someone to care for her. Don’t take advantage of her, or the situation. Your good karma toward her at this critical time will come back to you one hundred fold over time. And you should always be mindful of your karma – as I mention numerous times throughout this site. [See the discussion on Bad Karma / Good Karma in the section on Attitude Adjustment / Mental Makeover 2.0 in Midlife Bachelor Personal Makeover.

6) Recognize that you do not compete with the dead.  You won’t ever be the man her husband was – so do not try to be. Everyone is simply different and unique – not “better” nor “worse”. It is not that her dead husband is her #1 – he was during his time previously. That was the past, and now there can be a new #1 … a new “love of her life”. Just let it happen naturally … and don’t inject your own potential insecurities into the situation. She will love you even more for not creating any competitive feelings.

7) Be respectful of the children, the family, and any other fixtures in her life.  Again – your good karma in this regard will come back to you one hundred fold over time. Your best bet really is to let her make her own decisions with respect to everything involving the children, her dead husband’s family, the house, any investments, … anything. If she asks for your opinion, try to be objective (not competitive, not jealous) and don’t permit your own insecurities from interfering with giving her solid advice.

The motto of is “Leverage the Midlife Knowledge” – which means learn from one another, and share … so that we can all benefit from one another’s experiences. Everything in this Short Midlife Article was derived from this discussion thread:

Dating a Widow discussion thread in our Midlife Forum

here on There is also a follow-up thread which discusses the challenges surrounding the children involved in a widow-dating situation:

Take Off from the Widow Thread in our Midlife Forum

I encourage you to join the Midlife Forum, and contribute to the community … most of us are in our 30s, 40s, or early 50s. And we are all going through the same things – so why not share, and grow together? You can also add any comments or thoughts you have on this particular article down below using our Echo/Add Comment feature.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.