“In-Confidence” Anonymous Series Round-Up: Feb 3-10 2019

“I never thought this would be my life.

I just assumed I would meet my prince charming young, we’d have a wonderful love story, and have many babies. After all, that’s what happened to all my friends. And in all the movies. 
Yet, here I am: a 30+ woman who is still going on first date after first date to no avail.

Each date is just so draining. One hour long date involves the anticipation before the date, the hours spent on hair and makeup, the hope that this will finally be the one and the crash right after the date. Sometimes, the crash comes later- after date 2, or 3, or 4…but it always comes. Most of the time you know it’s coming. You feel the awkwardness or you yourself are the one to end it. Sometimes though, it completely blindsides you. Sometimes, you convince yourself that this is it: this is the one. And as fast as it took to convince yourself is how fast you get that slap in the face: “you’re a great girl…but you’re not for me.” My favorite is when I’m told “we’re not a match…” after one date. How can you possibly tell that after one hour?! What makes us not a match? That we don’t have absolutely everything in common? The date seemed fine to me!

Everyone wants to offer their feedback about why I’m still single in the hopes that their advice will solve my problems:

“You’re so wonderful, how can you still be single?”
“Maybe the right guy isn’t in NY?”
“You should lose weight- or take a professional photo for your profile- or lie on your profile about what you want.”
“You’re too picky.”
“You should always give a second date- even if he’s weird.”

People are well-intentioned- most do mean well. They just don’t know what to say. Or they just don’t fully understand this process- I didn’t either until I was in it myself.

Because the truth is:
I don’t know why I’m still single. 
Maybe the right guy isn’t in NY, but this is where I already moved to find love and I won’t move again with the false hope that the right guy is in Timbuktu.
I have lost weight. I did take a professional photo and I have lied on my profile and to myself about what it is I want. 
Is not wanting to date someone who is 50, jobless, and not socially aware picky?!
I often give a second date- even if he’s weird.

Maybe there just isn’t an answer even if that’s all everyone is searching for.

I often wonder how shidduch dating is for men. As a woman, I can say that it is such a demoralizing, demeaning experience. I have no control over anything. Hardly any matches get sent to me, so I don’t have the luxury of being picky. When one is sent to me, I have to go out with him because what if this will be my only option for months? I have to wait days for a guy to get in contact with me after he agreed to the match. When he does finally contact me, I have to be available at any given moment to have an extended phone conversation before the first date. He gets to choose the location of the date- regardless of my preference. He has to end the date otherwise it’s seen as a crush to his ego. Then, I have to wait to see if he wants to go out again: Wait by the phone for a guy I’m not even into. Sometimes they call- sometimes they don’t.

The hardest part of all of this though is the toll it has taken on my emuna. I became religious at 16 and used to feel so lucky for that choice. I wore my skirts with pride. I always made sure to say “baruch hashem.” I was the poster child for spirituality and for commitment to Judaism. But now, I feel so hopeless. I question now if G-d is listening. I question if G-d will say yes to my tefilot. I tell myself of course and at the right time and yet, I struggle believing it. How could G-d say no to me? I’ve been asking for over ten years to find love- why must the answer be no? How can G-d who puts so much value on marriage and family allow so many singles to struggle? I chose this path believing it would provide me with the family life I never grew up with. Yet, G-d won’t allow me the opportunity to build that family.

I don’t have the answers to these questions. What I do know is that all this dating for marriage isn’t getting me married. And at this point, I don’t know what will.”


“There are four words that every single woman dreads hearing, frum or not frum, Jewish or Christian. They might surprise you in that they aren’t “He said he’s busy,” or “He said no thanks” or even “He’s just not attracted.” Don’t get me wrong, these aren’t fun or enjoyable to hear either but the dreaded four words that I am talking about cause much more frustration for your single friends than you realize or intend.

Imagine it’s a Thursday night, your single friend calls to tell you about her really bad date. She tells you that, undoubtedly, this will be the last date with this young man and she plans on ending it very soon thereafter. She pauses for a moment and quickly says “So now that I’m single again, please keep me in mind and let me know if you think of anyone for me.” She exhales, proud of her ability to ask for what she really wants, a question that is surprisingly difficult to say out loud even to the closest of friends and you respond with those four dreaded words.

“I don’t know anyone.”

They are usually preceded with an apology, “I really want to help you, I know it’s so hard but…” Every single woman has definitely heard these words at some point in her dating career, from friends, siblings, parents, parent’s friends or cousins and no one realizes how difficult they can be to hear.

Let me give you a glimpse into why these words are hard to swallow. Asking a friend or parent or sibling to set you up puts a single woman in a surprisingly vulnerable position. It is an admission that there is something that they lack and want your help attaining. Anyone can attest to the fact that putting yourself out there in any situation is difficult. I know that when you hear the request you often don’t realize the difficulty that went into making it because I don’t either. It’s harder than it sounds to ask for things you want in life. Single women often feel “awkward” or embarrassed or desperate when asking this of close friends. Whatever the reasoning, asking someone to keep you mind or think of guys for you to date is a shockingly difficult task.

By asking you to think for them, your friends are turning to you as a glimmer of hope. They are praying that by expressing their wants to you and asking for help, perhaps you will come up with their next date and assuage their fears. They are looking around in their own community and realizing that their prospects are slimming and perhaps thinking in that self-deprecating way of being single, “maybe all the good ones are married already.” So they finally put themselves out there and what do you do? You validate every single one of their fears. You reinforce the notion that there is no one else out there.

You don’t realize you’re doing it and I too am guilty of it, as these words are such an easy “out” in the moment. But you know you don’t mean it. What you mean to say is that you can’t think of anyone right then and there.

If there is one thing that you can do to help your single friends it’s this: when asked by a friend to set them up pause for a moment, smile warmly and simply tell them “I’ll keep you in mind” or “Thanks for reminding me, I’ll think about it.” By saying this you let them know they aren’t alone and hopefully won’t be alone for the rest of their lives. There are men out there for them to meet. Even better, ask them more about what they’re looking for and what has and hasn’t worked for them in the past.

Quite frankly, saying you don’t know anyone is simply untrue. You have brothers, brothers-in-law, neighbors, cousins, classmates, work friends etc. who are all an excellent network and if you really wanted to do a second nice thing for your single friends you would then sit down for a few minutes and get creative. Our world could benefit from friends setting each other up. We often know our friends better than our own families do and if you spent a few minutes scrolling through your Facebook friends you could probably find at least one young man to message on your single friend’s behalf.

Unlike many other issues that our friends struggle with where the most you can provide is a shoulder to cry on or a listening ear, when it comes to dating there are concrete steps you can take to help your friends, sisters, cousins, nieces and neighbors. At the very least you can remind them that you’re keeping them in mind. Give it a whirl and it may even result in a nice gift or a chalek in olam haba.”


“I have been following the Layers Project for a while, reading every essay that comes through and anxiously awaiting each follow-up post. I know there will be a happy ending, because these people chose to share their faces and names with the public. People with happy endings are generous and open to sharing their stories with the altruistic hope of inspiring others. I appreciate it, and I know others do too.

But what about those of us who don’t have a happy ending? What if we don’t know when our happy ending will come, or start to doubt its imminence? What if we keep lowering our expectations, and our definition of a happy ending, in the hopes of some relatively happy ending?

I grew up in the Orthodox community, went to an all-girls school and all-girls camps. We didn’t touch boys—we were shomer negiah and proud of it. Throughout high school, seminary & college, I was proud to say that I was “shomer”. But now I’m 30 years old, unmarried, and I regret all those years of being shomer, or what I sometimes call “missed opportunity”. Because at least, maybe, I could have known what it feels like to be desired and receive physical affection.

I am 30 years old and I have never been kissed, on the mouth, by a man. I have never walked in the street wrapped under the warm arm of a man. I have never slept in the same bed as a man. And this is just the PG stuff. When people discuss their “firsts”, I can’t participate, because I don’t have a first. When friends discuss their preference for being the “little spoon” or the “big spoon,” I don’t utter a word, because I don’t know. I think I would prefer being the little spoon, I think, but I can’t tell you for sure, because I never tried.

My family can’t understand why I cringe when I notice my brother & sister-in-law holding hands under the table. My friends don’t get why I look away from their “PDA.” I look away because I want it too, and because when I can’t see it in my near future, it hurts. Sometimes the pain of not knowing when I too will get to feel physical love & affection is so great that I feel sad all day, until I’m strong enough to close off my mind and move on to the more productive outlets of emailing shadchanim, signing up for singles events, and “putting myself out there.” Then I feel as if I tried. As if I’m one step closer to being enveloped in the bear hug of a person who actively chose to spend the rest of his life with me. Or even some part of his life with me. Because at 30 years old, I have never had a boyfriend.

At 30 years old, I have never been in a serious relationship. I go on dates. Sometimes 3, sometimes 4, sometimes 5. But then it fizzles. And with the end of yet another potential relationship, a little piece of me dies along with it. I try to be compassionate when friends cry to me over their breakups. When they wail and say they’ll never find anyone as good as the person they just lost. I show that I care, and I do care. But there’s a part of me, a small part, thinking “at least you had this. At least you got to feel loved for 3 months, 6 months, 5 years.” They say it’s better to have loved and lost than never to have loved at all, and at this point in my life I believe that wholeheartedly. I know heartbreak hurts, and I am not belittling it, but for a smart part of your life, your heart was full. You were able to walk down the street with a full stride, knowing that someone was thinking about you, eagerly waiting to hear from you, waiting until you got out of work so he could call you and hear your voice. I never had that. Year after year, no one sends me flowers on my birthday. When I turn on my phone on a Saturday night, there is no text asking me how Shabbat was. When I return from a vacation, there is no one waiting at the airport.

I live my life alone, but this essay is not written to complain. I am writing to let those of you in relationships know not to take it for granted. Little things that you come to expect are things us “singles” can only dream of. And for those of you in a similar place to me, because I know you’re out there, Let’s band together and fills in those gaps for each other. Be a listening ear, a cheerleader, a well-wisher to your friends when you know there is no significant other for them to lean on, because real queens fix each other’s crowns. And when the day finally comes, and the “One” we’ve been searching for is found, let’s rejoice in the little things and be happy for each other, because strong women lift each other up.”


“If I’m honest with myself I was not ready to get married at twenty. By the time I reached my mid-twenties I was ready and in a good place. I had my college degree, a job I was proud of and had started traveling with friends to fill my time. My twenties came and went, made easier by the fact that my close friends were just starting to get married at that point.

Turning 30 seemed like a huge milestone. I had moved out on my own by then and settled in a new community. I was welcomed warmly and I connected with many of the neighborhood families. I built up a business and seemed happy and settled to everyone. However inside I was struggling with my lack of marriage, lack of relationships and generally even lack of dates.

I can’t say that my thirties flew by- they kind of dragged and I was always hopeful that things were about to change. But I cannot even compare the agony of turning 30 to that of turning 40. While our society seems to treat singles the same regardless of age, there is just no way to describe the difference. In my twenties, I looked forward to a full life hoping for a wonderful spouse and hoping to raise children. In my 30’s I knew I was coming in late to the game but I also brought in life experience that I knew would make it an easier adjustment to marriage and parenthood. And now here I am in my forties hoping and praying that maybe I can at least find someone for companionship.

The women in my age bracket who are lucky enough to meet someone are marrying men who were previously married. Many of them have already raised their children and married them off. At this age, we are expected to come in as a wife and companion and hopefully fill the role of Grandmother to the grandchildren of these men. We have skipped over so much. Yet when I complain of being single I’m told it can still happen. As if when it happens that negates 25 years of pain, 25 years of longing, 25 years of adult life spent alone.

So I guess my advice to others who interact with singles would be to treat everyone respectfully and sympathetically. Which may mean one thing for the 20-something-year-old who may still be young in your eyes yet is having a hard time already. and something different for the 30 something-year-old who deserves respect and admiration for her accomplishments and some validation for her loneliness. and something even different for the middle-aged woman- not girl – who feels that life has passed her by.”


“Back when I was in high school, my school hosted a popular speaker who lectured about Shomer Negiyah and how important it was to ‘save yourself’ for marriage. I don’t remember everything she said, but there was definitely a strong fear component to it; a sense that if you weren’t Shomer, you were ruined, damaged goods, and your Yichud room, wedding night, and subsequent sex life with your husband would be very anticlimactic.

I remember sitting there thinking how getting married was years away for me and that I had some real growing up to do. I longed to be in love, to have the emotional and physical closeness of a spouse, to hold and be held, to share myself with someone. Shomer Negiyah was presented to me as a long delay of gratification, an investment, the key to winning the biggest stuffed animal at the fair.

I knew there were people around me who were Shomer and those who were not. What I didn’t know that there was a third category, of people who said they were Shomer but privately were not. But I don’t think I fully understood the internal conflicts because I hadn’t yet been in situations where my discipline in this realm was truly tested.

Until it was. And I felt like a total failure.

It was my first relationship after coming back from seminary and we had been dating for a few months. Being Shomer was important to us and something that we believed in as an ideal. But as we spent more time together, the sexual tension grew stronger and stronger. Looking back, I was experiencing something very healthy—feeling extremely turned on by someone I was dating—but I didn’t know how to relate to the feeling because sexuality was often shamed, something to ignore, or it just wasn’t acknowledged at all.

The first time I broke Shomer Negiyah, I was convinced I got pregnant.

It really wasn’t physically possible given how “far” we went. And we were both fully clothed—I made sure my black tights and denim skirt stayed on the whole time.

I got over the pregnancy fear after a few days and laughed that I even thought that it was possible. But as time went on, some really difficult emotions began to rise to the surface and they pierced my identity like sharp knives: I had broken Shomer Negiyah and I felt like a fraud, an insincere Jew, and a bad girl.

After that first time we “slipped”, we swore it would never happen again. “We got it out of our system,” we told ourselves, as though making out was like fulfilling a desire to go skydiving. But that one time turned into another, and then into another, and I found myself going into a really dark place. I didn’t feel like I could talk about it with my friends; I didn’t want their judgment and I didn’t want the news of what I had done spreading. But looking back, it probably would have been helpful for me to be able to talk to someone about what was going on because it took up so much space inside of me. 
Since Shomer Negiyah relates to sexuality, the struggles and emotions around it often stay in an isolated, shameful place. Other areas of difficult Halacha don’t carry the same reluctance to discuss openly—after all, are people embarrassed to say they struggle with not speaking Lashon Hara or remembering to say Brachot? Some people feel haunted by their sexual past and even fear that current adversities may be because they weren’t more strict about Shomer Negiyah when they were younger. Do people have those fears about being disrespectful to their parents? Usually not.

I’m intentionally not going to share what the outcome was of that relationship—I’ll keep you guessing as to whether it ended or that guy is now my husband—because that’s not the point of my essay. I felt a need to share about this because this isn’t talked about much, and while I agree that we don’t need to share with the world all the private details of our relationships, the fears of sharing about Shomer Negiyah can have some really detrimental effects on us—not just on how we feel about ourselves, but on how we navigate our relationships.

I used to think that my Shomer Negiyah infractions made me a hypocrite. But now I look back at those times and just see a woman who was coming into her own—trying to figure out who I was, what I wanted in life, what I enjoyed, and how it all fit into the religious identity that is so core of my being.
I don’t look back at that time with nostalgia, and I believe I needed to go through those experiences to become the person I am today. Long gone are the days of standing in shul on Yom Kippur fearing that Hashem only sees me for my sins—what a gift not to be there anymore.

But I wish that during that time I had a more gentle approach in the way I viewed myself; less shaming, less perfectionist, and more open to the idea that maybe my challenges weren’t as unique as I thought them to be. And that if I had spoken to someone about what I was up to in my relationship sexually, it would have been easier to get clarity on what I wanted and validation that I was struggling. I wouldn’t expect a religious figure for an endorsement of behavior that goes against Halacha, but I wonder if more religious figures could provide a safe space for people to explore sexual issues they are grappling with without judgment.

As peers, we can aspire to provide that for each other.
Years later, I’ve had conversations with friends and colleagues who share my story, from all different backgrounds and dating cultures. Women feeling ashamed about their sexual explorations is not exclusively an Orthodox thing or even a Jewish thing, but I think that because of Shomer Negiyah we have added barriers to feeling comfortable talking about it. 
For me, taking the risks to share with trusted others about my experiences and finding out that I wasn’t alone was a game-changer. Getting empathy about an experience doesn’t make us become proud of it; it makes us feel more human about it. And when we feel human and can see ourselves not merely as a balance sheet of good versus bad, there is new capacity for emotional growth, self-compassion, and expansion in our relationship with ourselves, others, and God.”


“I always considered myself a late bloomer. I was finding myself playing catch up specifically with relationships. I am by no means old and I know I have time, being just 27. Yet, I have always felt pressure from my family, friends, and community growing up to date and get married. When I was younger I chose to only date for marriage (not that I had any idea what that really meant). So, I was the odd one out during high school being single.

My first boyfriend was while on my gap year in Israel. He was a learning experience that left me feeling empty and sad. Why wasn’t I attracted to him? Why could I only look at him like a brother? I was in no way prepared for the dating world and, looking back, I don’t think I even wanted to go out with him. I did it purely out of pressure and wanting to be accepted by my peers. I was constantly hearing how nice it was to always have someone to speak to about everything. Isn’t that what friends are for? To always have someone to go out and do things with. Isn’t that what friends are for? To have a shoulder to cry on and an ear that will listen. Again, friends…?

My friends were all of those for me so I never felt the inner push to find it elsewhere. Creating synthetic emotions was damaging to myself. I continued going out with different guys after coming home and going to college. There was always a recurring theme: I felt nothing for them when it was over and the relationship had failed. It was drilled into my head that if I was single I must be sad and alone. I believed the lie.

It took me moving to another country alone, barely knowing anybody, to take time for myself. I enjoyed being single. I wasn’t sad or alone; I had my friends and family and they are my most precious blessings. Of course, I had always dreamed one day I would get married. But after all the difficult and failed relationships, I was convinced it wasn’t in the cards for me. And I was okay with that. I came to terms that I didn’t need a man to complete my life.

Falling in love with myself was a breakthrough for me. I starting making decisions for me that I had been avoiding because I knew it would ruin my chances of dating. I just needed to start living my life.

I moved again, this time to a hilltop in the middle of nowhere. People didn’t understand why a young single girl would move to somewhere inaccessible. I was told it would be extremely difficult to date. I was no longer willing to keep my life and dreams on hold. I did the legwork and traveled hours for dates. I did it to prove to other people and myself that it was important to me. It didn’t sit well with me that I was doing it to make others happy.

Yes, I would love to have a family one day. I’d love to meet my “soulmate”, but I needed to breathe, transition, and enjoy the moment before dating and getting married so my grandparents can stop asking me when I will give them grandchildren. I needed to be happy again and to be comfortable in my own skin.

I am so glad I did. My relationship with Ha-Sh-em improved, my connection with my friends, and my own self-care became a top priority.

Then, suddenly, when I least expected it he was there. All of my expectations for what would be right and good for me was out the window. Everything I had built for myself was only strengthened by him, not torn down. Through my ongoing journey, my perspective has changed so much. I am glad I took that time I had to focus on me. That I took the chance to live my own life and follow my dreams.

I still remember how I had felt when all my friends were getting engaged and married and I was feeling like something was wrong with me because I couldn’t find “the one”. Nothing is or was wrong with me. It all is meant to happen in the right time. I do my best to remember all the pressure was out of love and concern. This allows me to do my best to be sensitive and respectful to my friends who are single. I should not pressure them, but I should support them for whatever their decisions are.”


“No. No. No. 
“Don’t say no.”  “You have to listen.” “Listen”
No. No. No.
“Excuse me? Did you just say no?” “Listen to me.”
No…? Y…yes. Yes.

And slowly our no is turned into a yes. 

As a child, perhaps one of the most important lessons we are taught is how to say yes, and listen to authority. To our parents, to our teachers, to our babysitters… and the list continues. 

Perhaps, there is another lesson that needs to be taught as well— when to say no, and how to have that ‘no’ respected, in a way where it is not turned into a ‘yes’ by those around us. 

Since I have started dating, I’d say the biggest challenge I have faced, is plucking up the guts to say no. Whether it be a no to the date idea or to the food choice.  Whether it be a no to walking outside in the freezing cold for miles because he wants some fresh air or a no to a second date. Or… a no when he wants to touch me.

The most important lesson I have learned, is how to say no, and then owning that NO. Saying no to being touched is ok. Even if he says he feels rejected when I say I am shomer negia. I am still entitled to say NO. And he is obligated to respect that. 

So after that first date when he tried, and I said no, and he sighed with an eye roll, I should have seen the sign. But somehow, after asking a respected person for advice, I was told to give it another try. And the second time, when I said no again, and he told me he feels rejected, I should have left him standing alone in the street. The third time, when he grabbed my arm and tried to pull me onto the bench next to him, I should have pulled loose and run away, leaving him sitting by himself. But slowly my ‘no’ was overruled, as those I asked advice from told me to not make him feel rejected; and as he told me I was being too stringent. 

It was not until I finally spoke to my best friend that I realized the insanity of the situation. Gradually, my defenses had worn down, in such a subtle way, I didn’t even realize the situation was slowly growing into one of a much more serious nature. Without her support, I would never have been able to come forward and say NO with as much conviction as I did on that day we broke up. I learned a very valuable lesson that day.

Regardless of how the person may appear on the outside, and regardless of what others say, always always trust yourself. Your gut is right. You are entitled to say no, to say yes, to say maybe. Stand up for yourself as needed and trust your instincts. 

I have learned a lot during my dating experiences. However, the most valuable lesson I have learned: No means no. So, yes, it is important to teach children to listen to authority sometimes. However, it must also be taught about the importance of the word no. And how other people need to respect that no. 

So, as strange as it may seem, as I approach my late 20’s, I can finally say that I have learned to say NO with conviction. And I will own that no, saying it with my head held high and with no regrets, as it is a valuable word that in the right circumstances can be said with pride. 

I guess the advice I’d like to pass on, is the importance of standing up for yourself. Don’t feel bad saying no if a certain situation makes you uncomfortable. Don’t feel bad taking a stand, and speaking out on a date if something does not feel right to you. No means no. And every single human has a right to use the word and have that word respected. If the no is not respected, then saying no to that second date is something that needs to be done with confidence and pride. Because no is not a word to shy away from. It is a word that can have great power and in certain situations can and must be used.”

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Shira Lankin Sheps graduated from Hunter College School of Social Work with an MSW in clinical social work. After working in the clinical field, marketing and photojournalism, she decided to start The Layers Project to help break down stigma and promote healing within our Jewish community. She feels strongly about presenting women, who are so often shown as shallow characters or fully removed from Jewish media spaces, as three-dimensional individuals whose lives are full and rich with resilience. Shira is the founder, Publisher and CEO of The Layers Project Magazine.