DATING FORUM

By: Baila Sebrow

Question

So much has happened I don’t know even know where to begin. I’ll try to keep it short. For many years I was married to a tzaddekes who was taken from me in the prime of her life. Immediately after her passing, my friends started pushing me to go out with their divorced lady friend. My children didn’t like the idea, probably because of her history, but they also knew how lonely I was. At the same time, my daughter’s neighbor has been widowed for a long time and is a frequent guest in her home. I got to know her and we started dating. I’m not proud of it because nowadays it’s not done, but I ended up dating both ladies at the same time.

When I started dating the first lady, my friends started pushing me to marry her, so I did. It turned out to be a big mistake. We were both unhappy and later divorced. Not long after, I called the widow to go out with her and she told me she doesn’t date divorced men. Now I don’t know if she’s saying that because I married the other lady and she’s angry with me or because she really feels that way about divorced men. Do you think I should continue pursuing her or move on?

Response

I need to first preface my response by apologizing to you for not responding to your query as quickly as I would have liked to. I’m acutely aware there are times when readers identify strongly with a situation brought to this column, and who at times take it very personally. I have no doubt that this article may affect some people, so please know that I gave this matter extra deep consideration.

This is a complicated situation because there are two separate issues regarding the widowed lady. Her feelings about dating divorced men, and the hurt she may have felt when she found out that you were dating another woman while dating her, and that you chose someone else to marry. The latter is something that any woman regardless of being widowed or not would take offense to. Think about it for a moment. Can you imagine how betrayed she felt when she found out that you were two-timing her? In all probability, she feels that she can’t trust you.

The other issue is that yes, there are widowed people who will not date divorced people and are advised against it by well-meaning and knowledgeable people. On the other hand, divorced people are advised to seek out widowed people to marry as they assume it is better for their standing. As a shadchan, unless a divorced man is a kohen who halachically cannot marry a gerusha (divorced woman), I will try to match him with someone divorced or never married. With widows who reach out to me for a shidduch, I will do my best to match them with a widower. I want to make something very clear: this has nothing to do with one rank being better than the other; rather, it’s about compatibility.

People who have lost a spouse due to death typically find a sense of compatibility with each other because they have shared a profound life experience that is very different from divorce. That’s not to say that a widow and a divorced man cannot have a successful relationship. Many do. But there are differences in emotional history, expectations, and the way each approaches a new partnership that should be taken into account.

There are good reasons why widows and widowers may connect deeply with each other in ways they can’t with someone who is divorced. For one thing, they understand grief and permanent loss. A widow or widower has experienced losing someone through death and the complicated emotions of missing a spouse, honoring their past marriage, and carrying those memories into a new relationship. Neither person has to explain why certain dates, places, songs, or memories carry certain emotional weight.

Widowed people often share a similar view of marriage. Widowed people had a marriage that ended because of death, a circumstance beyond human control. They may approach remarriage with gratitude, maturity, and an appreciation for companionship because they know what it means to have lost a lifelong partner.

There can be less comparison and resentment. Divorce often involves conflict, disappointment, betrayal, anger, financial issues, custody concerns, or unresolved wounds. A divorced person may still be processing those experiences. A widowed person may have a different emotional landscape, mourning what was lost rather than healing from a relationship that ended by choice.

Widowed people understand that a first spouse is not competition. I know of relationships where the divorced parter resents whenever the widowed partner says something that makes them feel as if they are competing with a ghost. A widowed person’s deceased spouse will always have a place in their heart. However, if their partner is also a widow, they often intuitively understand that loving someone new does not erase the late spouse who came before. They both may have more comfort with the idea that the past is part of the person, not a threat to the present.

In relationships where one partner is divorced and the other is widowed, they may share similar life-stage adjustments. Both have had to rebuild their lives, manage loneliness, raise children alone, make major decisions independently, and rediscover themselves after losing a partner.

To be fair, compatibility depends far more on the individuals than their labels. A divorced person who has done deep emotional work, healed from the past, and is ready for a healthy relationship may be a wonderful match for a widowed person. Conversely, two widowed people can struggle if one is still emotionally unavailable or unable to make room for a new relationship. The key question is if this person has made peace with their past and are emotionally available to build a future with someone else.

Now that we’ve tackled all the emotional stuff that could be going on with the widowed lady, back to you. It sounds like you were grieving deeply after losing your wife, whom you describe with great admiration. When someone loses a spouse after many years of marriage, the loneliness can be overwhelming, and it is understandable that people around you wanted to help you rebuild your life. However, it also sounds like you allowed the pressure of friends to influence a decision that ultimately wasn’t right for you.

The widow may have seen things differently. From her perspective, she may have developed a connection with you and then watched you pursue and marry someone else. Even if you were not committed to her at the time, she may have felt rejected or like she was second choice. When you returned after your divorce, she may have felt that the door had already closed.

At the same time, she may genuinely have a personal boundary that she does not want to date divorced men. People have different comfort levels and life experiences, especially widows who may have their own reasons for wanting a certain type of relationship. It’s not necessarily a judgment against you.

I would not recommend continuing to pursue her or trying to convince her to change her mind. In fact, I strongly advise against it. That could make her feel pressured, and many women (especially widows) typically resent that. However, if you truly feel there was something meaningful between you two, one respectful conversation may be worthwhile. You could acknowledge what happened, take responsibility, and ask if her decision is truly about divorce or if there is hurt from the past. You can tell her that you respect her feelings and you don’t want to pressure her. Admit that you realize that your behavior while dating her may have hurt her, even though that was never your intention. Make it super clear that if her decision not to date you is because she doesn’t date divorced men, you will respect that. But if there is any part of it that comes from how things unfolded, you would appreciate the chance to talk honestly. Then let her answer guide you. If she says no after that conversation, the healthiest thing is to accept it with dignity and allow yourself to find someone who sees the man you are today, not the mistake you made.

The larger lesson here is that major life decisions, especially after losing a spouse, need to come from your own heart and judgment, not from the urgency or wishes of well-meaning friends. A second marriage deserves the same thoughtfulness as the first. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].