Dating after death or divorce

Suggestions for Those Delving into Dating after Death or Divorce | How To Meet Someone | The Challenges

I lost my spouse almost a year and a half ago. He was only 52. I miss him terribly. I miss the life we shared. With Doug, I found truth in the saying that when you are in a good relationship, your joys are doubled and your sorrows are cut in half. After Doug's death, my sorrows were doubled and there was no joy. I assumed that my life was over, and that I would never be lucky enough to love again. I was wrong.

I did meet someone. In many respects, it has been absolutely wonderful. However, there have been serious challenges at times. I suspect that many adults who re-engage after the loss of a spouse, whether it be through death or divorce, encounter issues when they begin dating again after decades of marriage. Fortunately, I didn't have to deal with some of these, but that doesn't mean you won't. I think it is good to be prepared and realistic, while still being hopeful, and giving love and life a chance again.


So, if you have not given up on life, and are ready to try dating again - now what? Here are some suggestions that may or may not work for you. Please keep in mind that I'm not a counselor or a dating expert - I'm just someone like you.

Be prepared for challenges, disappointments, surprises, and ANFGO (Another F**king Growth Opportunity)

  • Sometimes I forget that my world has changed. I was used to being married, being within a committed relationship, where we were in it together for the long haul, for better or for worse, operating as a team. Dating is not the same. It takes time to develop that kind of relationship. Manage expectations accordingly.
    • Keep in mind you may not be able to get away with some things you did after being married for decades, like leaving your dirty underwear on the floor. (Maybe this wasn't a good idea back then either :-)
    • You will probably need to create new boundaries.
    • If your goal is to replace what you lost, be prepared for disappointment. A new relationship with a different person will be different. That could be a good thing.
  • Follow standard dating advice. For example, the first time you meet, drive yourself and choose a neutral place (like a coffee shop) where you can escape if there is no interest. If you do want to get to know them better, follow up with a date-like dinner in a nice, quiet, but not too pricey restaurant where you can talk.
    • Keep things relatively light and positive on the first date. This is not the time to go into detail about death, divorce court battles or bouts with diverticulitis.
    • Even if you are nervous, consider setting a 1-2 drink limit (if you drink) for the first date to keep your head clear. Also, you don't want to come across as a lush, or do something ill-advised. Although I admit that Doug and I both got plastered on our first date.
  • If your friends are setting you up, consider a double date to start. It might be more comfortable.
  • Don't forget romance. Make your own memories together. Don't settle in too quickly to a routine. A date a week can keep a relationship growing over the long term.
  • Don't constantly talk about your previous spouse. (I found this incredibly difficult. I'm not sure anyone but another widower would have understood.)
  • Honor your partner's loss if they had one. Lots of widows/widowers have a shrine (photos, memorabilia) and many good memories that they don't want to bury along with their spouse. They may still love their dead spouse. Unless it is really obsessive and scary, allow it. Try not to be threatened by it, or consumed by jealousy. They are dead. You are alive. Again, this could be harder for a non-widower to understand.
  • Try not to compare. (This was my biggest challenge.) Respect and enjoy the differences between the new person and your previous partner.
  • Don't bring the person into your family until you think there is potential for something longer term. Otherwise it can be awkward and confusing for all involved.
  • I wouldn't recommend dating anyone who is only separated (not divorced) unless you are willing to get dragged into the divorce proceedings, or to get dumped if they get back together. It is also probably not a good idea to get involved with someone whose spouse is dying.
  • Try to be flexible and compassionate.
  • Don't disclose too much too early on your financial situation. Gold diggers do exist.
  • Try to balance your head with your heart.
  • Worry about sexually transmitted diseases. These days, few people over 15 are virgins. They may have had multiple partners over the years. If you sleep with them, you are also sleeping with everyone their partner slept with as well. An estimated one quarter of people who have AIDS don't know it. Condoms provide protection, but I think it is wise and caring to get tested and ask your partner to do the same. Unless of course you are willing to die from HIV, deal with herpes outbreaks for the rest of your life, or undergo six months of chemotherapy for Hepatitis C.
  • I can't offer any thoughts on dealing with children, as I don't have any. I assume you will need to be ready for some serious bumps. Unfortunately, some parents will be put in a position where they feel they must choose between their new partner and their children. I'm guessing many will probably put their children first.
  • Be realistic. Some 50 year old men think that 20 year old women are going to be interested in them. I guess this is possible, but the 20 year old may be looking for a parent, not a partner. Didn't work out well for Demi Moore and Ashton Kutchner.
  • Realize that after a serious relationship ends, people may go into a "transitional" relationship. It may offer healing and regrouping, but not end up being long term.
  • Take care of yourself. Be true and honest with yourself (about your needs) and with the other person. Pretending to be something you are not will not work over the long haul.
  • Pay attention to your other commitments - family, job, household, etc.
  • They say most people give more thought and time to choosing a car than to choosing a spouse. Try to be patient. Don't make any rash, difficult-to-reverse decisions early in the process, like selling your house and moving in with (or marrying) someone you hardly know. The standard advice is to wait a year before making any major life decisions (financial, residential or marital.) I'd recommend a year and a half.
  • Don't give up too quickly. Give yourself a limit - e.g., ten dates with ten different people before you give up on a particular approach (like Internet dating.)
  • Don't settle. Being alone is far better than being with an incompatible or toxic person.
  • If you have no interest, cut someone loose quickly but kindly. Don't waste their time or yours.
  • And last and most importantly - open your heart to the possibilities. I hope you will be pleasantly surprised. I certainly was.


Meeting a suitable companion can be difficult once you are out of college or the work force, or if your job doesn't offer opportunities to meet single people. Try approaching this as looking for someone to do things with, or to talk to, or a companion, versus shopping for a replacement mate. If you do happen to meet someone compatible, let it evolve, see where it goes. This takes some of the pressure off.

  • Be open to the possibilities. Go someplace you wouldn't normally go. If you feel too shy to go to a dinner party, go anyway. Take a class. Participate in a volunteer event. Join a gym, book club or organization associated with one of your personal interests or passions.
  • Let your friends know you're interested in meeting someone. Let them know your criteria, if you have any beyond a pulse :-).
    • Having some "must have" criteria helps:
      • avoid wasting time (yours and theirs)
      • avoid a re-run (if your previous relationship was not good)
      • add some objectivity to the process.
  • Commercials claim that today, 20% of relationships start online. For some it has been a disaster - unsuitable matches, embarrassment, lack of response, crazy people, deception and disappointment. Others really have found true love - I know several! I would guess that much endurance is required. It also might be hard not to feel pathetic about the process. Maybe try to give it at least a dozen strikes before calling yourself "out."
    • There are paid sites, free sites,and sites that specialize - e.g., by faith (Christian, Jewish), interests (e.g., active adults who like to hike), goals (e.g., fun versus a serious relationship) or seniors. See a review of sites for people over 40, along with some tips on how to get the best results with online dating. See 10/5/2011 New York Times article on seniors online, Love at First Click.
    • I would guess the people you would meet through a paid site might be more reliable and serious about dating.
    • You might also try a personal ad in a publication related to your interests, if you want to meet someone who shares those interests.


Any one of these can make or break a relationship, if you let it.

  • TIMING. People around you will probably have opinions about what constitutes "too soon." They may want to protect you, or they may be concerned about irrational decisions made in the midst of grief. In my opinion, this is a personal matter, and thus the timing is up to you. You are the best person to judge when you are ready. However, do try to be honest with yourself about whether you really are whole enough to get involved with another.

  • BAGGAGE. Few people over 30 don't have any.
    • Emotional . Depending on how your past relationship ended, there can be serious issues that can complicate things or come between you. Like Grief. Anger. Guilt. Fear. Trust.
      • After a loss (divorce qualifies as loss), one's ability to participate in a new relationship will depend on the stage of grief they are in at the time.
      • Some people get into a relationship in an attempt to fill a void. Loneliness can drive some bad choices.
      • Most widows/widowers are "broken" to some extent.

        Many of us still feel married after the loss, so dating can feel like betrayal. Personally, although I said the words "Til death do us part," in my heart I thought it was forever. I wanted 40 more years with him. The Universe did not grant me that option.

        Initially, I was absolutely appalled at the idea of dating. Some widowers never get past this. Some divorced people are so angry or burnt that they can't envision it. My own marriage was happy and rewarding, which I think made me more open to the possibilities. When I met someone without trying, it blossomed naturally. However, PS and I did see a grief/relationship counselor together to deal with the emotional pull of the past and our fear of future loss.
      • Familial
        • Deceased spouses - You might think it will be easier to date a widowed person versus someone who was divorced. That depends on a lot of things, including whether they have placed their dead spouse on a pedestal. No real, living person will be able to compare.
        • Ex-spouses - maybe even a crazy one. If one or both parties have children, the ex-spouse may be in your life long-term, whether you like it or not.
        • Children - some of whom may be needy or still living with the person you date. They may hate the guts of the new person in their parent's life, or simply freak out over the thought of their parent seeing or marrying anyone new. If you both have children, they may not get along with each other. Blending families offers many unique challenges.
        • Aging parents - living with or dependent on you or the person you get involved with
        • In-laws - If you thought dealing with two sets of in-laws was a challenge, try four sets.
        • Pets - This may seem trivial, but if you have a cat and he has a dog; or he/she hates or is allergic to your pet, then what?
        • Friends - You may be ready to date. Are your friends ready for you to date? Seeing you with someone else may be hard for them. It may be an all too painful reminder that the past is past. They may not like the new person in your life. You may end up parting ways as a result.
    • Financial - including the possibility of serious debt. The average American has a credit card balance of about $16,000, and some people have way more. Even if they are not irresponsible spenders, lots of parents have college loans. As a friend of Doug's so aptly noted, sending your kids to college these days is like buying a very expensive car every year and then driving it off a cliff and buying another. Multiply $50 grand a year x four years x 2.3 kids - the math isn't pretty. Many divorced people also have alimony or child support payments.
    • Residential - If you are lucky, you might both own a home. If you decide to move in together, which house do you choose? Will the owner be able to open it up to be a shared home? Or do you both sell or rent your places and buy a new one? Selling and buying multiple properties and then moving is time consuming, expensive and stressful.
      • Stuff - Divorced people often end up with half of the couple's possessions. A widower has both people's possessions. One widower + one widower = 4 people's stuff. If you move in together, which stuff do you keep?

  • CLUELESSNESS - if you haven't dated for decades, the protocols may be unclear. Is it okay for a woman to ask a guy out? Where do you go? What do you talk about? How are you supposed to act? Who pays for what? What about the physical part of the relationship?

  • TIME PRESSURE - When you are in your 20's or 30's, you think you have your whole life ahead of you. When you are in your 50's or 60's, you might only have a decade or two of quality time together.

    • An attractively, newly widowed woman was horrified when a man asked her out - she could not imagine sleeping with someone new. Her daughter told her not to worry - most elderly men are not looking for love - they just want someone to do their laundry or change their diapers (or a "purse and a nurse.")
    • The mother of a friend of mine was widowed. She remarried. One year later she learned her new husband had Alzheimer's. She spent the next six years caring for someone who didn't recognize her. It would be different to have this happen after decades of quality time together.
    • Aging can affect the physical aspect of a relationship. Data from the Massachusetts Male Aging Study indicates that the prevalence of erectile dysfunction of any degree is 39% in men 40 years old, and 67% in those aged 70 years. Women 45 and up can be struggling with the physical, emotional and mental impacts of menopause.
    • In her book Widowed, Dr. Joyce Brothers included a good chapter on dating. She noted that it is quite different to take your clothes off in front of someone who loves you and has watched you age gradually over the decades.

  • SET IN WAYS - the older we get, the more we tend to get set in our ways. How you spend your time. When you go to bed and what side you sleep on. Which gender is responsible for washing the dishes or taking out the garbage. What you watch on TV. Etc.

    • A new relationship can be full of fun and exciting surprises. What is missing is shared history. The "remember when" and special memories that add understanding and depth. That only comes from years spent together. Perhaps you will be lucky enough to have an opportunity to create a new history, and new life with someone else. But it will only happen if you give it a try, and are willing to open your heart and risk again.





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