Dear Goldy:
I need to know how to help my brother. He’s 43 and doesn’t know how to date, which is why he’s still single. I love and think the world of him. I want him to find his bashert, who will love and appreciate him as he deserves.
So, what’s the issue? When he dates, he doesn’t have a rhythm, a vibe, a flow. I’m not sure what word to use. He’ll pick the oddest topics because he wants to discuss things that “she hasn’t spoken about on every other date.” He wants the date to be memorable and not to blend in with all other dates she’s had. So, he’ll bring up topics that are obscure. He may have what to say about it, but the women don’t, or if they do, they think it’s weird to discuss it on a first date. I know this, because I have tried to set him up and have heard this from the women as well as from a couple of shadchanim I’ve contacted on his behalf. I’ve been told he brought up the Stanford Prison Experiment, a psychological study conducted in the 1970s, how dead bodies are left on Mt. Everest (and, because of the cold, the body doesn’t decompose), why Mary Todd Lincoln is among the most hated First Ladies, etc. I can understand him asking a question to start a conversation such as: What scared you most as a child, or what’s the worst present you ever received, and how did you react when given it? But these topics are cringe-worthy.
I spoke with my brother about this a few times. I’ve even given him a list I printed out of “conversation starters” for dates. He says he wants to see how well rounded the woman is, by what she knows about the topics he suggests. I told him it wasn’t for him to test the woman on general knowledge; the first date is just about getting to know the other person. He doesn’t date as much as he used to, but I don’t know if it’s because of his age or because of his weird discussion topics. I don’t want to insult or hurt him by saying he may be his own worst enemy, but he is!
What else can I do?
Sharon
*****
Thank you for your email, Sharon.
I love how you’re trying to help your brother by talking to shadchanim and setting him up yourself. Who knows someone better than a sibling? You know what type of woman your brother is looking for and, more importantly, what type of woman he needs. Some siblings don’t even try to help, so I’ll start by saying your brother is lucky to have you. You also want your brother to face the reality that he is his own worst enemy by choosing to speak about odd and not well-known topics. I had to look up the Stanford Prison Experiment. Why would anyone talk about it on a date, let alone a first date. I would come home from a date with him thinking he was some sort of oddball. That’s why it must hurt you that your brother is still single, and he isn’t helping the matter. You see him for the amazing person he is and not for the oddball he (may) projects on dates. I can understand your brother wanting the first date to be memorable for the woman, but he should want to be remembered fondly. A woman should reflect on the date she just had with your brother and want to go out again, not tell the shadchan, “No.”
Sharon, you were right in telling your brother that it isn’t up to him to test the woman’s knowledge. If he wants to do that, bring along Trivial Pursuit and play it. This way he can see how well rounded the woman is, but the woman (and your brother) can have a good time while doing so and she doesn’t have to know about him “testing her.” The first date is for getting to know each other. There doesn’t have to be a deep conversation. Whatever happened to “just have fun.” If you think your brother overthinks first dates, and this is his way of making up for it, let your brother know that nerves and anxiety are normal with dating, but just let things flow and not force anything, especially a unique topic of conversation.
If it were my brother, I too, would have given him a list of “great conversation starters for first dates.” There are a ton of them on the Web. But apparently, your brother wants to stand out from the crowd. Being an individual and unique isn’t always a good thing, though. Sure, the woman will remember talking about a psychological experiment where strangers tortured each other and what having power does to people (I recommend Spiderman: With great power comes great responsibility). But she’ll remember him as the one who spoke about torture. You must come right out and tell him that his plan isn’t working – as he is still single, and he should switch things up. He can still be unique and memorable, but find some other way to be so. He can plan unique but lovely dates (again refer to Google). I remember being taken on a picnic once. In all my years of dating, I’ve only been on one picnic. I also remember the first fellow who bought me a small gift on a date – he won a stuffed animal from the claw machine. Small acts and forward-thinking can go a long way.
There are ways to be remembered for the good and not the creepy or strange. I can’t answer if his topics of conversation are the reasons why he is single. Does he always choose such non-popular topics of conversation? I’m sure he has had a few conversations that aren’t cringeworthy or leave the woman wondering. Dating is hard enough as it is, and for all we know, someone didn’t like his job, hair color, nose... But you probably did hit the nail on the head. Speak with your brother. Like I mentioned before, have him change up his game, no pun intended. Keep helping him. You are his best ally and you’re also a female, so your insight to what a woman may think of as odd or strange is much needed. Your brother is lucky to have you.
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 This email address is being protected from spambots. You need JavaScript enabled to view it..
