This emailer thought I would be the perfect person to ask advice from because of my story. While it may seem that way, there were many twists, turns, obstacles, and hardships from date number one with my husband until he stepped on the glass under the chupah. My story isn’t your typical story. But I did my best with how I responded.

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Dear Goldy:

There are a few frum people who work in my office. We are all friends because of circumstances. It’s not like we separate ourselves from others in the office, but when there is an office lunch or event, we sit together because we are the only ones eating kosher and can relate to one another’s lives. You get my point.

Before COVID, a frum man began working in the office. He works in a different department, but we run into each other in the hallway, kitchen, etc. We worked remotely from home until a few months ago, and now we are all back in the office. I find myself wanting to ask him out. We are around the same age, both single, we have some similar interests from brief conversations we have had. But I’m scared: What if he turns me down? Then it’ll just be awkward. What if we date once or twice and it doesn’t work out? Then it will also be awkward. I know you and your husband worked together in the same organization for years before you dated. I wanted to know if you think I should bite the bullet and ask him out for lunch or something casual like that to start with, and what to do if he turns me down.

Sherri

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Thank you for your email, Sherri.

I see you have been paying attention to my column and know how my husband and I met. But things were not simple at all, and if you would have asked me (like a friend did in the beginning) if I would have ended up marrying my husband, I would have said no and given you a list of reasons. But only Hashem is in control and He had a plan. From the first time my husband asked me out until our wedding, it must have been close to three years. There were lots of ups and downs in those years and in the prior years leading up to us dating. My story can’t really be generalized to others, but I’ll see if I can help you out as best as I can, by telling you my true thoughts and feelings about this.

Firstly, Sherri, if you do end up asking your officemate out, please check the human resources handbook if there is a policy about employees dating each other. Many employers don’t want “inter-office romances,” because productivity may go down with the employees in question, and if the relationship doesn’t work out, they want all to remain professional in the office. There have been incidents where, after a break-up between workmates or officemates, things got ugly in the office – such as name calling or purposeful avoidance of each other – thereby making other officemates have to run interference and messenger between the two if they actually do work in the same department and must interact with each other daily.

Secondly, I love that you are willing to take the initiative and do the asking! Forget about waiting in your castle tower for the prince. Get on your horse and go get him! Lol! If you know that this fellow is single and you feel that he may be interested in you (you didn’t provide much detail, so I don’t know), then go ahead. Suggest a coffee break outside of the office, such as a local Starbucks or Dunkin’ Donuts. Make it casual: “I can’t stand the coffee here. I’m going to make a run to the corner for some real coffee. Want to join?” You mentioned that you shared some common interests; you can start up a conversation not work-related if you get the opportunity, if others aren’t within earshot. “Did you see that no hitter last night?! Amazing!” or “Did you hear about de Bozo’s, excuse me, de Blasio’s latest press conference? I mean is this guy for real? He said…” One conversation can lead to a second which may lead to a third. This is also an opportunity for you to see how he reacts when you speak with him about non-work-related issues. Is he shocked and taken aback thinking the two of you work together and that’s where it should start and end, or does he think, “She follows baseball so closely. She’s okay...” Take your cues from him.

Thirdly, who cares if he turns you down? Nothing ventured, nothing gained – heard of that? If you don’t take the chance and try to grab the brass ring, you’ll never know. You may think this is easy for Goldy to say because my story ended with a mitzvah tantz, but you’d be wrong. I once dated a fellow for close to two months and really liked him. I began imagining a life with him. I bit the silver bullet and, at the end of one of the dates, I was the one who asked him out for another date. You can guess how it went because he and I are not married, but I’m so glad that I took the chance. And I learned from that experience.

I also remember a time when I was 16 or 17 in the bungalow colony and thinking that one of the teenage boys I had grown up with every summer was good looking and turning into a real mentch. I didn’t have any game plan. I just came out one day and told him how I felt about him. Turns out he had a girlfriend I didn’t know about. Okay, great. I wanted the ground to swallow me whole; but after a day or two, we were right back to hanging out with the rest of the gang without any awkwardness. Turns out he actually married his girlfriend, and they have a beautiful family (I checked a few years ago on Facebook).

Sherri, nothing will ever be given to you or anyone else on a silver platter. And as I was once told and have told to many others since, “Nothing worthwhile is easy; if it was, everyone would be doing it.” Asking someone out, even for a casual date, takes courage – yes, courage. This would be one situation in life when you ask a question that you honestly don’t know the response it will illicit, and that is a scary moment to live in. But grab life by the horns and don’t think about the “what ifs.” If he says no, then you know. If you never ask, you’ll never know and always wonder. And if he does say no, that’s okay. It’s not a reflection on you; as you said, you don’t know him very well, so that means he doesn’t know you well. He isn’t rejecting Sherri; he will be rejecting the opportunity to get to know his workmate on a different level. That’s it. If that happens, brush yourself off and move on. If he says yes, then brush your hair and go out.

To answer your last scenario: What if the two of you date for a time or two or for a while, and then break up? It happens. Be mature about it. If you are the one who broke up with him, don’t make it awkward when you see each other in the hall or kitchen. Don’t go out of your way to avoid him; talk to him. But if he was the one who broke up with you, yes feelings will be hurt, but act like the mature adult you are. Go to work, hold your head high and don’t make it awkward if you see each other in the hall or kitchen. Don’t go out of your way to avoid talking to him. Basically, act the same in both situations.

I would advise not to tell any of your workmates what you want to do or if you do go out, that you are dating. You don’t need to be the topic of office gossip. Remember, you may spend 40 hours a week with them, but they are not your friends, unless you talk to them or get together with them outside of work. I remember telling my friend and co-worker Rochelle that I was dating my husband when I was at her house for a Shabbos. Rochelle and I were friends; I was close with her and her family and very excited about dating my husband. At that point we had been dating for a while. Rochelle and I were in her kitchen preparing dessert and I blurted it out. She looked stunned, stopped the prep, and just looked at me, “From the IT department?” She was in shock and had to recover. Then all the questions began. I swore her to secrecy, and she was a vault. When co-workers found out that she had known for weeks, they yelled at her for not sharing the news. But Rochelle is a true friend.

Sherri, I can only wish you hatzlachah in whatever you decide to do and how to do it. Just know that if things don’t work out as planned, that it wasn’t bashert for now or at all, and that Hashem has His own plan for 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..

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