Frum and Gay: Part One

"…I need to break it off, right?"

I wanted to share a fascinating saga that came my way recently- I think it can help other people in difficult situations.

Two separate people reached out to me by email, both asking for some chizzuk (they each called it advice). As it turns out… they are actually brothers!

As you’ll see, it was suspicious right away that these were brothers sharing two angles of the same story, but of course I couldn’t say anything. Also, I didn’t really know; it was just a (really strong, educated, backed up by a lot of circumstantial evidence) hunch. But I responded to one of them mentioning that I’d once spoken to someone describing a situation much like his brother’s and was able to share perspective about it because of that previous dialogue. He suspected and verified.

Both had to shamefully admit to each other that they read Substack blogs… ;)

(I remember as a kid reading a series where each book was written from a different kid in the class’s perspective (I forget the name) - this was a real life version of that!)

Both brothers kindly gave me permission to share this story, after we changed a few identifying details and got their full okay.

I share it not for the humor - as you’ll see it isn’t actually very humorous, though it is fascinating - but for the fact that people can learn from it.

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Left mostly intact (including the nauseating compliments, t4…) except some verifying details, here is how it all began. Get your tissues out.

On _, __, 2025 at 2:43 AM _ <_@gmail.com> wrote

Shulman,

I enjoy your posts and I love hearing your refreshing perspectives. I particularly enjoy your open-mindedness which expresses itself not just in your ability to see another side, but in your clear respect and love for another fellow Jew. It’s rare to see someone who has such obviously strong opinions, along with the capacity to really see another perspective, which, in my opinion, clearly comes because of your love for everyone. Hashem should give you strength to keep growing, helping, inspiring and being a sweet voice of reason in this crazy world.

I am reaching out because I don’t know who to turn to. I need someone who understands people, and also understands that people can be different. I don’t know you, which is another plus, and you seem like you may be able to help give me some advice.

This is all very raw and almost surreal (in a negative way), so I’m a little all over the place about it. I’m going to try to organize my thoughts as best as I can, but I apologize if it’s messy.

Basically, I am engaged to a very sweet girl and everyone is so happy for me. But after a few days, I just can’t anymore.

You see, I like… guys.

If you get the gist.

Growing up I was always quirky and I always felt like I didn’t fully fit in, but I didn’t really mind. But after a while, it turned out that my quirkiness wasn’t really quirkiness; it was queerness. (Well, they used to mean the same thing.)

This became a whole struggle while dorming in Yeshiva, but hey, every guy has his celibacy struggles so things weren’t so different for me. I shteiged and I loved Gemara and really, I was just a regular guy in Yeshiva.

Honestly, I’m thankful to Hashem that I had the opportunity to be able to ignore this for all the 9+ years of yeshiva; it allowed me to grow and appreciate true Torah b’iyun and all the good stuff that comes along with that. The system honestly worked for me - it even helped, since my quirkiness was seen as a sidebar in deference to the fact that I was super “shtark.” (You can decide if a model which doesn’t promote normalcy is actually good or bad - I’m just saying it worked in my favor).

When shidduchim time came, everything changed, and I received poor advice which made things even worse.

What happened was, bikitzur: I decided to speak to my Mashgiach. I was already in Lakewood at this point, but I made a special trip because I thought he would understand. We were very close through my years in Yeshiva and he seemed like a baal eitzah to me.

Apparently, though not surprisingly, he had never dealt with anything like this before. Either because it never came up. Or because no one ever confided with him about it. And I don’t think he really understood.

For my part, this was a big, big, BIG deal. I had never told anyone, so this is me bearing the deepest, darkest parts of my soul. Almost what they call coming out of the closet. Even though I’m a pretty level-headed guy and I had the scenario of how it was going to go played out in my head, the way it came out was not amazing (I wasn’t about to tell me venerated mashgiach, “Hey, I’m gay!”)

As things happened, he basically told me that I’ll meet the right girl and things will be fine (it was a little more complicated, and there was some advice that was very helpful but that’s the gist).

And it was really bad advice.

I got redt to a nice girl, and we went out. I even went back to my mashgiach again and he basically said that I should follow my heart. If I don’t feel it, I should break it off.

Great, right?

But.

…he added that it is very common to not really feel a connection before marriage and for many it comes only after. Look at the chassidim - they have these beshows and it works! You think they have a connection from a little meeting like that? No! But it develops. So I should think about it long and hard.

I followed his advice - I thought about it long and hard.

And really, I did think she was pretty, but I just didn’t feel “into it.” In our culture, we don’t really talk about anything too intense until pretty late so in my mind it was all about family and being a father. I’d make a great father!

Well, stupidity plus ignorance times more stupidity got the better of me and with the unintended, faux encouragement from the mashgiach, I was like, “I could make this work!” In short, I was stupid, naive, thoughtless and even careless, and I went forward with it.

I played the part and six days ago we got engaged. The grin on my face was frozen during my lechaim and I kind of knew this was going to hurt her. I didn’t really know, but I knew. I don’t know if that makes sense, but I don’t know if anything really makes sense. I don’t know what I knew or what I know but the point is that here I am and this happened.

I really liked her as a friend. We had a real connection. She was fun, cute and adorable. We had really, really good, engaging conversations. We clicked. But, you know: not in that way. And if it’s not in that way, she was going to be hurt.

I know what the right thing is. I know I have to break it off. I don’t know why I’m reaching out. I think I just need a listening ear who won’t judge and I can vent to and come out of the closet while still staying in the closet (I don’t consider my meeting with the mashgiach as coming out like I had hoped).

I do have real questions about my purpose in life - getting married is not an option which is really sad, but where does that leave me? I’m going to be the nebach 40 year old who everyone pities? The even more nebach 80 year old? The one who, by my levaya, some strangers (even good friends are just not family) are going to pretend to care? I am almost crying writing this, but I want to share this too. This is me coming out of the closet, while staying in the closet, so all masks are off as I express my hidden fears, while keeping my actual self unexpressed.

It’s quite liberating. I should’ve done this years ago, gosh! (Thanks again for following me through this.)

I guess my immediate question is: maybe I really should get married and have kids? I can fake it and make her happy, and we’ll have kids and a family and live life together. I’m never having any other life anyways, so I’ll really give it my best shot. But at the same time, who am I kidding? There’s no way i can fake it. I did the research and it doesn’t end happily for her. I can’t take that chance, and I need to let her find someone she deserves. I’m not actually torn, but I also am torn. I’m so torn even though I know exactly what I have to do.

Also, once I break it off, how will I give my parents nachas? If I get married, maybe I’ll hurt her, but if I break it off, what will be with my parents? Maybe I really can fake it and make her happy and make my parents happy. Writing this sounds so silly because it’s so obvious that it’s stupid. But I’m still torn and… is anything obvious?

Another thing: I did everything right. I learned nicely (and I imagine I’ll continue to), I do mitzvos nicely. But I can’t get married and I can’t ever love someone. That’s really hard, and it feels cruel and mean. I really believe that Hashem somehow knows what’s best for me; I don’t mean that as a joke. But it feels so cruel. And it’s been affecting my relationship with Him - try having a relationship with the One you know is really hurting you! I see the angry face in front of me and I want to turn away. Not the inviting smiley face you probably see. Sure, it’s a test and it will be good, but all I see in front of my face is the cruelty. Don’t get me wrong, some days are good. But it’s a struggle. And now I’m dealing with having to hurt another girl because of bad advice + my stupidity in order not to hurt her in the future. And what do I tell my family?

I’ve vented, and I reread it and it’s messy, but I’m leaving it because my soul is in there.

Here are the takeaways:

1. …I need to break it off, right?

2. What do I tell my family about why I’m breaking up?

3. How do I continue a relationship with Him when I feel like this is pretty cruel? (I wasn’t planning on adding this above, but it came out, probably for the better)

4. What is my purpose in life?

5. Family is so important and so central to our culture and religion. How do I fit in with that picture?

6. Do I tell my parents I’m gay? They’ll be so hurt.

7. How do I wrap my head around the fact that I am going to be the nebach?

Okay. I think that’s that for now. Thanks for listening.

___

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My response (fwiw lol):

On _, __, 2025 at 1:20 PM _ <davidschulmannn@gmail.com> wrote

Dear ___

Whoa. Whoa whoa whoa.

Sorry in advance, this is waaay above my pay grade.

That was one of the most beautiful emails I’ve ever read. I’ve seen pain on people’s faces. I’ve seen pain in songs. I’ve seen pain in poems, paintings and in numbers on arms. But I never read a simple, unpoetic email so raw and stirring.

I’m surprised you didn’t have a harder time in Yeshiva with tons of guys around. Unlike your description that “well, everyone has their celibacy struggles,” well, what if they were in a co-ed school? Your attitude is unbelievable, and you must realize that you’ve really done something special!

I am amazed that despite the pain, you are still trying to do the right thing and if you feel any pain down here, up there the malachim now understand why the Torah was given to man- even an angel couldn’t withstand what you need to face. Without any of the glory - quite the opposite; the fear, the shame - as you agonizingly described. This won’t make you feel better on a rainy day, and it won’t make it easier, but it’s still true.

If this helps at all, you can always reach out. I’d love to get to know you better.

I have so so many thoughts flying around about so many things you wrote, but I honestly have little to really say apart for some measly words of encouragement. And sympathy - for the bad advice, for the pain, for the worries, for the loneliness.

But something I can do is respond directly to the questions you posed, so let’s do that:

I need to break it off, right?

Yes.😞You hit the nail on the head that you need to rip off the band-aid and inflict some pain and embarrassment now to cause much less pain in the future. That is the kindest route you can take. It should be done as sensitively as possible - and you probably need some excuse (one that won’t hurt her) if you’re not going to reveal why - but it must be done.

The best would be if you could be open to her in complete discretion, but I don’t know if you’re up to that or if it makes sense.

What do I tell my family?

You can do what you want (and I can help brainstorm excuses), but if you can muster the courage, and assuming your parents are somewhat normal and open-minded, you should tell them the truth.

It will be painful and really hard, but you will then have them for support and understanding. Your parents probably won’t be thrilled, but I promise, a loving parent would rather know the problem and be in pain with you than allow you to torment yourself alone. But only you can decide to do that, if and when you’re ready.

Btw, just keep in mind that if you make up an excuse, you’re going to need more excuses moving forward. It can get sticky.

How do I continue a relationship with Him when I feel like this is pretty cruel (I wasn’t planning on adding this above, but it came out, probably for the better)

Oh my. If you want to vent more, feel free. It sounds like hell.

I have no advice to offer, but I can help carry the burden with you, and listen, and be a shoulder to cry on.

I can just say one thing, that even if you want to try to move past this, that won’t happen by ignoring it and pretending everything is good. It’s not. Sure, it will be good in the end somehow, but that doesn’t make it good now. When facing things like this, aderaba- one needs to work on the answer while fully appreciating the question, not by minimizing it.

I’ll give an example of how I bring this out: Rabi Akiva always said כל מה דעביד רחמנא לטב עביד. And that’s considered a really big deal (it may even be the highest madreiga anyone ever reached, not for now). But what’s the big deal? Every fourth grade girl says the same thing.

The answer is obvious- the fourth grader doesn’t even understand the question. Rabi Akiva spent his entire life working on this question (כל ימי) and only then could he reach that madreiga. The fact that your religion is making you suffer isn’t something you should just tell yourself, “it’s all for the best” and move on. Even if you can come to that, which is a madreiga, that can only be reached as a reality through the appreciation of the question.

Abie Rotenberg’s song, Teardrop, is a really powerful depiction of this: you have the right to cry.

🎵 “The angels had told her it’s alright to cry.” 🎵

No one should tell you right now, “don’t worry, it will be good.” Or “grow up, just look at the big picture” (which you can’t even see right now). Even if there is a bigger picture (there is bH:) and these are building you up for opportunities and they are growing pains, they are pains and they hurt! After you take the time to process, we can focus on the healing and growing.

What is my purpose in life?

Family is so important and so central to our culture and religion. How do I fit in with that picture?

How do I wrap my head around the fact that I am going to be the nebach in only ten years from now?

These are really loaded questions, and these are exactly what processing is about. But even processing has steps, and I don’t think it’s time to deal with these just yet. First let’s tackle the immediate situation at hand: you need to break up with her, and you need to think about “coming out” to your parents. We’ll hopefully share more exchanges in the future where we can work on these together. Makes sense?

Do I tell my parents? So that they are not disappointed when I break it off? When I say no to the next girl? They’ll be hurt either way.

If you can, like we said, rip off the band-aid! (Really easy to say; really hard to do.)

I’ll stress again, I think it will be painful, but they also want to know. It hurts to see a child in pain but a parent wants to know about the child’s pain so they can help and protect and love. All a parent wants is that their child not feel alone.

Unless you tell me otherwise, I assume your parents are normal. That would mean that they probably won’t react perfectly. They’re human too. But give them a couple days and ultimately they’ll be your absolutely biggest support. They will be able to help you far beyond what an anonymous blogger can...

I am so much looking forward to hearing back.

Best,

shulman

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to be continued…