I received an email from a sister who was asked to help her single brother out in dating and finding his bashert. The sister felt that her brother was ruining his chances with everyone she set him up with because of what he would tell his dates and what he would disclose about his life to them. When she spoke with her brother about this, he seemed indifferent and not appreciative of all her efforts. He claimed that he was being honest with these women, laying all cards on the table, so there aren’t any surprises later on. But there is a fine line of being truthful and volunteering information no one asked about that you know will paint you in a bad light. The sister wanted to stop setting her brother up and wanted to know what I thought about the situation.

Dear Goldy:

This letter is about my brother and not me. I’m not sure what to do, but I know what I don’t want to do: I don’t want to try to set my brother up with girls anymore. I am married and have a family of my own. My brother is three years younger than me and still single. My husband and I always wondered why he was single because he’s your typical “great guy,” but now we understand why. He sabotages himself with girls he dates! He volunteers information about himself that he wasn’t even asked about, and then calls the girl closed-minded when she gets back to me saying, “He’s really not for me.”

About six months ago, my parents asked if I can help my brother out with dating. They know I have some single friends and I am very social, and they thought I may know of a girl who would be appropriate for him. They said he hasn’t dated in a while and was getting more and more depressed as his friends were getting married all around him. I said I would do what I can. I spoke with my brother about what he was looking for and what he wanted, and he became defensive, saying he was doing just fine and didn’t need my help. I let that slide because I can understand that it can be embarrassing for people asking for help or for people thinking they need help in the dating department. Finally, when he calmed down, he told me what he was looking for and told me that he only wanted the best and not some “sad tz’dakah case.” I ignored his comment, telling him I can only promise to try hard.

The first girl I set him up with was a nice girl from my shul who seemed to fit the criteria of what my brother wanted. After the first date, the girl called me, saying that my brother seemed to be investigating her and grilled her with questions about what was on her social media pages. She said it was almost like he studied up on her and it was a little scary that he knew so much, and he had made many assumptions about her and her lifestyle, much of which were not true. I apologized on my brother’s behalf and made a joke about how everyone is always on social media and he was probably just doing basic research – that we can all be guilty of doing. The girl told me some of what my brother questioned her about, and I understood why this girl called it scary. When I spoke with my brother about it, he said he wasn’t concerned because it was like this girl was living two lives. He actually said that she posts things about herself and when she’s asked about it, she clams up: “Why’s she pretending to be one way when she isn’t.” He wouldn’t listen to any advice I was trying to give him and said that he was glad that she didn’t want to date him again because he had no desire to ever see that “two-faced girl” again.

The next girl I set him up with didn’t even meet him before she called me and said that she was able to tell that my brother wasn’t for her just from their ten-minute phone call. I didn’t want to ask what was said in ten minutes, but I had to. The girl told me that my brother volunteered the information that he works so hard during the week and likes to take it easy on Shabbos, so he won’t go to shul on most Shabbasos and just sleeps in. He mentioned that he dislikes it when my mother tries to wake him up to go to the late minyan, because he doesn’t want to be forced to go to shul and he’ll go if and when he wants, but he stays in bed most of the day on Shabbos. The girl said that she would also love to sleep late on Shabbos, but she goes to shul and then after lunch takes a nap to catch up on sleep. She actually said that she wants a husband who wants to go to shul on Shabbos, and it means something to her when she sees people pushing themselves to do the right thing even if they don’t want to, and the fact that my brother had such a blasé attitude for shul and davening wasn’t something she could support. She didn’t want to be a nagging wife, nagging her new husband to go to shul or even daven. “He’s not my teenage son that I have to chase out of bed.” Again, I couldn’t blame her. But my brother thought she was the crazy one. He said that he was just being truthful so there are no surprises later on.

The last girl I set him up with, last week, had a story that was the icing on the cake and has me throwing up my hands in surrender when it came to setting up my brother again. She told me that, on the date, my brother asked if she watched television on Shabbos. She said she was shocked at the question. She told me that my brother equated having a Shabbos clock set up to turn lights on and off on Shabbos as the same thing as a clock turning the television on during Shabbos. She said that my brother told her that he has set the television in his room to turn on if there is a sports game he wants to watch on Friday night or Shabbos afternoon. I could not believe what I was hearing. My brother has a room in the basement of my parents’ house and I am positive that my parents know nothing about this. They wouldn’t stand for it! I told the girl that I was unaware of this new fact and asked her if she was sure my brother was telling the truth or just making a joke (which I feared he wasn’t making). She said that my brother was serious and even said he has the television set on mute so his parents wouldn’t hear and they would think he went to bed early or is taking a Shabbos nap.

Goldy, I give up. I spoke with my brother and told him that he was doing himself a disservice by volunteering all of this information about himself. I told him that no frum girl wants to be told anything of what he was telling them, and that life won’t always be like this – he may want to move more to the right and actually want to go to shul on Shabbos and stop watching TV on Shabbos (I actually yelled at him about that). I asked if he wanted to get married or if he was happy as he was, because I was working hard at trying to set him up only to have him destroy his chances with any girl whom I suggest. Let me add that every time I tell him about a girl, he gives me a hard time, always asking why he should go out with her and why she is special. My brother said that he knows that he is supposed to get married, he’s not sure if he wants to, but knows that it’s time for him to settle down and move on with his life. I told him that he has to want it and it would be unfair to a girl if he marries her without wanting to be a good husband, friend, provider, and father. I give up. I just give up. When I told my parents I couldn’t do anything else for my brother because he is his own worst enemy at dating, they urged me to try some more. I couldn’t even bring myself to tell them about what I was told about my brother. It would break their heart to know what he thinks and what he does in their house!

Any advice?



Adele, thank you for your letter.

From what you have written, it certainly seems like you have tried your best by your brother. I’m trying to decide if I should give you my short answer with advice or the long answer. I’ll do a little bit of both.

You are right. Your brother seems to be sabotaging himself in the dating arena. It doesn’t sound as if he is appreciative of your efforts in the least, especially if you are saying that he argues with you every time you try to redt him a shidduch. He is volunteering information that paints him in a bad light to women. You are right when you wrote, “No frum girl wants to be told anything of what he was telling them.” It bothers me when you said that when you confronted your brother about all of this, he didn’t seem concerned and even said that he was dating for marriage purposes because it’s expected that he marries now. It seems like he is treating dating like it’s a job or an errand he has to take care of.

From what you have written, I think you have done your due diligence by your brother. You can’t be the only one expected to do all the work, while he sits back and in a sense ruins everything just by opening his mouth. If it was my brother, I wouldn’t try to help him until I see him make a real effort on his part to change. Not too long ago, I was also asked to help someone find his bashert. I am not a shadchan and never advertise myself to be one, but it was someone I knew well and she wanted me to help a mutual friend. I made some calls, was able to find a young woman who seemed to be his type. I told the woman all about him, including his level of frumkeit as well as what he wanted and what he was like (I don’t believe in embellishing the truth or hedging around unpleasant points, because eventually the truth will get out). The woman agreed to the date, but just as with your brother, my friend volunteered information during the first date that was not asked of him and information that really didn’t need to be disclosed; even I didn’t know some of what he told the woman. After the date, the woman told me afterwards that it was a miserable date and she thought that my friend needed to figure out what he was doing and what he wanted in life before he went on another date. When I spoke with my friend, he said he was just being honest and doesn’t want to play any games. I told him that being honest had nothing to do with what he told the woman, and it was almost as if he wanted to ruin things. I told him that I wasn’t going to waste my time if he wasn’t serious about dating. He said that was fine.

Adele, if your brother is, in fact, ruining his chances on purpose with whomever you set him up with, then stop. You tried to explain things to your parents without letting them in on what your brother is really doing in their house, but I don’t think they fully grasped what you were saying. Make it clear to them that you have exhausted all avenues and are at a dead end. Add to it that your brother doesn’t seem to care one way or the other, and until he puts some real effort in, you have to focus all your time and effort on your family – on your life. You can’t be the one doing all the work while your brother puts obstacle after obstacle in front of you when you are only trying to help him! It’s time your brother takes control and decides what he wants without making others jump through hoops. It may be hard, but sometimes you have to walk away.

Hatzlachah to you all!

Goldy Krantz  is an LMSW and a lifelong Queens resident, guest lecturer, and author of the shidduch dating book, The Best of My Worst and children’s book Where Has Zaidy Gone? She can be contacted at bestofmyworst@hotmail.com.

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