Why can’t people go out and have a good time on a date? And while they are having said good time, they can hopefully get to know each other? Why do some dates feel like a job interview? Yes, I know you are interviewing for the job as spouse, but some dates feel like a barrage of questions are being shot at you. It’s not a conversation, it’s a Q&A session. And let me tell ya somethin’: that’s not how you get to know someone.

You need to spend time with him, do things with her, let conversation flow, one topic to another. Believe me, you’ll find out more about him that way, rather than asking: “If you were trapped on a deserted island and only had one animal with you, which would it be and why?” and “What is your favorite color and explain the reason.” Those were two questions I was asked by a psychiatrist on our first and only date. Uh, excuse me? “I’d like to be stranded with an orangutan because they are human-like and smart. They would make very good companions, plus they can climb trees so we can get fruits to eat and branches and leaves to build a shelter.” And “Green. I like green because it’s a pretty color.”


Dear Goldy:

I am not new to dating. But it seems when I was younger, the dates were more fun than they are now. Sure, in the beginning I’d get taken to lounges and we’d spend hours talking, but as time went on and I became the Queen of First Dates, I’d be taken bowling, ice skating, to a baseball game, the US Open, picnics, ax throwing, etc.

It wasn’t too long ago when I thought I had met THE ONE. We had been dating and were both honest about what we wanted out of the relationship. It was headed towards engagement. But “when you plan, G-d laughs.” I know the breakup happened for some reason – which I can’t understand now – “but one day I’ll understand and know that it was the right thing to happen.” I’m just not at that point yet.

It was so hard to get back on the dating train. To start at the very beginning with someone – anyone, it didn’t matter who it was, but it was Square One. I’d have to go through everything that I thought had been done for the last time. But what choice do I have. I took time off from dating, as you have written about. When I felt ready, I agreed to go out with someone. But OMG, I can’t do this again if this is what it’s coming to.

I went out with a nice guy. He’s an accountant. I mention that because he’s not a doctor of any type. Not a PhD, not an MD. He’s not a doctor of podiatry, orthopedics, and certainly not a psychiatrist. I’m not writing all this because I want to date a doctor; I’m writing this because of the questions he asked. It’s like he was trying to get inside my head to understand me – which is creepy. I felt like I was in a mental health study where a PhD or MD would say one day, “In the study conducted in 2023, we asked 500 individuals...”

“What is your five-year plan?”

“What advice would you give your 20-year-old self?”

“And what do you think your 20-year-old self would be happy about, that you’ve accomplished, and disappointed about because you didn’t accomplish it, or it was never in the cards for you in the first place?”

My answer: “My five-year plan is to get married and begin a family. Have enough money for what’s needed and enough left over for an extra or two, and if that means I’m a working mother, then that’s fine. The advice I’d give myself is: Don’t get your hopes up until your 30s because your 20s were full of duds. And my 20-year-old would be happy that I’m successful with my job, friends, and family, and I don’t care what you think of these answers, but I’m brave enough to give them. But the 20-year-old me would be disappointed that I have to answer questions like this on a first date! Your whole line of questioning means nothing.”

It means nothing because none of the questions have to do with the “here and now and my current self.” Well, the five-year plan question had to do with the now and future, but did he want me to give a detailed answer regarding what I expect in every aspect of my life? These questions reveal nothing of who I am, what I like, what I want, what I enjoy doing, what I value most in life, how I feel about family, etc.

My date said that he never had the questions answered like that and the answers usually took up time making the conversation interesting. Let me get this straight: You’re following a script on a date? And you’re 40? You can’t just go with the flow? And this has worked with other girls because he said it’s not working here. It only tells me that he isn’t original and can’t go with the flow. So, I asked him, “You’re an accountant. Why? Is it because numbers can’t talk back? Is it because there’s only one right answer, and if you get the answer wrong, you can rework it until you get it right?”

I can’t do it. I’m starting from scratch again and I’m sitting opposite an accountant who thinks he’s Freud or something. Dating shouldn’t be like this. Is this what I have to expect now? I haven’t been on a first date in a long time, but have things changed so much? Why not just hand out questionnaires in the beginning of the date?



Thank you for your email, Devorah.

I am so sorry for what you are going through. I too once thought I found “the one,” but he wasn’t. I had to start from scratch just like you. It felt like I was mountain climbing, and just when I was about to reach the summit, there’s an avalanche and I slide back down to the foot of the mountain.

But now that you are back to climbing that mountain, I hear what you’re saying loud and clear. It’s like facing a firing squad instead of trying to find common ground to talk about. As soon as one question is answered, another question is hurled your way. That’s happened to me and I’m sure plenty of others. Some may say the questions are a way to begin a conversation or they’re a safety net for those who are socially awkward or shy. They ask the questions because it takes some pressure off of them. Some people can’t go with the flow; they like a schedule and a routine. Nothing is wrong with that, but a date is exactly the opposite of their comfort zone. Except for showing up at the pre- arranged time and address, everything else if really up to chance or spontaneous.

I don’t know if the man you were on a date with is shy, socially awkward, uncomfortable on dates, etc., but what I do know is if questions are asked, they should serve a purpose. The purpose here is getting to know you, and in a way, he could have gotten to know you a little better if you took the bait and started a long conversation as a response. But the questions he asked seemed more to me of those I’d be asked in a job interview, not on an interview of someone really trying to get to know me. I love the way you responded: very blunt, very deadpan, and within 20 seconds his thoughts that the conversation would carry on throughout the evening was over. Now what? Did he have a plan B? Part of me is sad for him, the other part is angry for you. I think he does this on all of his dates because he said that he really never had anyone react/respond as you did.

What you and I take for granted is our social abilities. I’m taking a chance by including you, but from what you wrote, I think you are comfortable in a crowd, with friends, on a date. I don’t understand why someone has an issue cold-calling someone for something about work, or something they need. I don’t understand why people sweat meeting new people or going to new places. These are things that are as easy for me as brushing my teeth every morning. But for the anxious, shy ones, it can play on their minds for weeks, leading up to the event, and they can make themselves sick over it.

I wouldn’t be too harsh on your date or others who have the script and questions ready. But I will advise them: Try jumping into the pool at the deep end. Don’t have a plan or script, because in life sometimes you can’t plan for all that happens, but you have to react to whatever it is and carry on. If you feel the person you’re dating may be nervous, you can do your part to make him feel less nervous and then the evening may go better. It may not be so scripted or awkward. But I do feel your pain. You want to just have a good time and you end up playing 20 questions. Hang in there. You will find the one that you have a good time with, whether he asks the right questions or not.

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.