Navigating the Dating Scene The Second Time Around

We talk about people having emotional baggage that they drag with them wherever they go. Let’s think about real baggage that we take on a trip. What each of us might pack for the journey will be different. When our bags get mixed up with someone else’s bags, we are not very happy about it and we feel disoriented. Now imagine that both your suitcase and someone else’s suitcase have been emptied and the contents are now mixed together in a larger bag without any kind of organization. This is the confusion and discomfort that can be involved in dating, especially if you are on the second time (or more) around.

If you were married before, regardless of whether you were widowed or divorced, you know that marriages are complicated and it takes a lot of work and energy to keep them strong. As we get older, things get even more complicated. There are often children, jobs, careers, aging parents, and commitments to our communities. Then, there is our own health, where more challenges develop as we age. 

My close friends know that I like to laugh about crazy dating experiences and I have performed a few comedy monologues about them. But even the craziest of dating experiences is one of learning and growth. Many men I have dated have been wonderful guys. They were just not the right wonderful guys for me.

When something goes wrong in a dating relationship and I notice too many red flags, I sometimes procrastinate ending it. As women, we are often socialized to not think of ourselves. Perhaps, though, this kind of decision is not just about us. Is it really fair to the man you are dating to spend time in a relationship with you when you cannot see a long-term future? It makes it even more difficult when one person feels a relationship is going well and the other one is trying to figure out how to end it gracefully. However, dragging out relationships with no future does not benefit anyone and wastes a lot of time that could have been spent in finding the right person. 

As a widow, when I experience a difficult date or end of a long-term relationship, the hole of grief opens wider. I start to miss my late husband even more as I know how far the date was from being someone I would ever want to marry. For a divorced person, it must be difficult as well, as this becomes another relationship that just cannot work out and they do not want to enter into another bad marriage.

While it is very difficult for so many of us, it is important to go into a relationship with an open mind. Often, we want to know everything about the person before we ever meet them. There is not only the photo, but also googling the person to see who they are on social media. If they have their own business, it can be helpful to see reviews about how they treat their customers. When on a date, observe how they treat the customer service people, i.e. waiters and waitresses, store clerks and others who offer assistance. For the younger generation in the shidduch world, we often hear about the crazy obsessions with how the family functions, what kind of tablecloth they use on Shabbat, and, the absolute craziest, what size dress the mother wears or what kind of car the family drives. I am fortunate that in my circles, as an older single, these questions are not usually raised. Our parents are either very elderly or deceased and we have been on our own for decades.

Don’t be too quick to judge someone totally based on physical appearance and fashion sense. Take a look first at what is inside the person. If you like what is inside, you will come to like what is on the outside. Keep in mind that not everyone is attracted to the same kind of person. We are all individuals and we each have different preferences.

It is important to tune in to what the other person says or does on a date. More importantly, however, and this is so hard for so many of us, tune in to how you feel about their words and their actions. It may not be rational, but if something makes you uncomfortable, validate your feelings and acknowledge them. Do not rely on the opinions of others. Your family and friends were not on the date with you and there is no way they can really know what happened and what is going on inside your head. 

When I date someone who is divorced, I become concerned if they spend a lot of time and energy complaining about how terrible their ex-wife was to them. In my mind, I get the message that I will become the next ex-wife and he will eventually be talking to someone else about how terrible I am. I have a great deal of respect for someone who acknowledges that he and his wife just weren’t a good match for one another and they made every effort to part ways gracefully, especially when there are children involved.

We have a serious problem with “get refusers,” men who hold grudges against their ex-wives,