Everyone enjoys a shidduch story, and the Where What When has asked me to start off their new column with a few of my shidduch experiences over the past many years. The new column, “Dating Perspectives,” will take the place of “Ask the Shadchan” and will feature a different writer each month.

The couples in the stories below may recognize themselves, but readers will not. They will, however, hopefully be entertained.

I have a good friend who put me down as a family reference on her children’s shidduch resumes. I have gotten phone calls over the years asking about the family. Now their youngest child is entering shidduchim, and the calls are starting again. The situation has changed, though. Being a good friend, I have information about this child that people might want to know. Watching her grow up, I have seen her in many situations, and my opinion of her is that she is selfish and has a difficult and unpleasant personality. I now feel uncomfortable answering questions. Should I tell or not tell? I said to my friend that maybe I am not doing a good job and she should take me off as a reference. She said, “Oh no, you know us so well.” But I don’t think she would want me to express my unflattering opinion to callers.

Our son is engaged to a lovely girl, and we are planning the chasana. I have already made two weddings. For both of our daughters, we and mechutanim were more or less on the same page as far as what kind of simcha we were comfortable with. Now we are dealing with the girl’s parents, who are well to do and have higher expectations for the wedding. I realized when the couple were dating that she came from a higher standard of living but thought it wouldn’t be a major problem. I guess I wasn’t thinking about the wedding.

To the Shadchan:

 I dated a girl for about half a year, and we finally got engaged. Then Corona hit. With lockdown, no large gatherings were allowed, and my kallah’s mother said, you can’t get married now. The mother is a “party lady” and has been looking forward to her only daughter’s wedding for a long time. My kallah and I said we’ll get married in a backyard with a minyan, but the mother said absolutely not. She told her daughter, “If he loves you, he will wait.” The mother was adamant, and the father went along with her. The grandparents got involved and gave their opinion: no.

It is now two years later. We are planning a wedding in a few months. The mother says that all the guests have to test for Covid before coming. I certainly don’t like that idea. At this point, I am having doubts about the marriage. My kallah is a wonderful person, and we have been through so much together (including a lot of arguments), but I am very concerned about the family and the influence they will have on us. At the beginning I thought they were the perfect family, loving and involved – my own parents are uninvolved in my life – and the siblings are great, etc. But this Covid situation has brought out some very controlling tendencies. I am also disappointed that my kallah didn’t have the backbone to stand up to her parents. Why is she listening to them and not to me?

I could still get out of it, but should I? As I said above, I am conflicted. I’ve put so much time into this relationship and would happily marry the girl – but I’m worried about her crazy family.

I am 28 years old and have been going out with a young man for a few weeks, and I am torn. He is crazy about me and is ready to get engaged. In fact, he hints at it every time we go out. I feel under tremendous pressure. I like him, and he meets a lot of qualities on my “list.” He is very smart. He is capable, honest, and hardworking. Yet, I find myself unable to say yes. I’m not sure what is holding me back. I just have a gut feeling that something is not right. Some of his behaviors bothered me, but I am not sure if they are significant or not. I enjoy his company, most of the time, more or less, but I don’t really miss him when we’re not together, and I don’t feel happy or excited about the prospect of getting engaged. If I say yes, it will be from a practical point of view. I am an “older single,” after all. By the way, I don’t think that going out longer will help me make up my mind. I see who he is. The dilemma for me is can I make a life with a good person who is offering me marriage, children, the whole deal, or should I take a chance on finding someone with whom I can share deeper feelings.

To the Shadchan:

 I’m a regular Baltimore guy in my mid-twenties with a good job. I met this really wonderful girl through a dating website. Before going out, I checked into her and her family superficially as I was not really expecting it to work out. Everything seemed okay – no big red flags for the things I thought I cared about. We have gone out now several times. The girl is very nice. She is warm and funny and pretty. She is educated and hardworking – all great.