Chananya Weissman
Chananya Weissman

A Month of Hell and Hope

We recently completed the most intense month of the Jewish year, beginning with the first recitation of Selichos (according to Ashkenazic custom, anyway) and concluding with Simchas Torah. It is a month jam-packed with prayer, mitzvos, food, family, shopping, and preparations. It is a roller-coaster of fasting and feasting, sleeping too little and sleeping too much, scrambling to keep up with work while planning time off. Hopefully among all the chaos there is also a spiritual renaissance and joy.

For singles long past the age when they were “supposed” to be married, it is a particularly confusing and difficult time. Allow me to share a glimpse of what this holiest of months is like for “older” singles.

* * *

You know it’s coming. You dread it and yearn for it at the same time. You dread it because you are going to be intensely lonely no matter where you go or who you are with. You dread it because you’ve been there and done that, you’ve put your heart and soul into it, given your very best effort, received a resounding “no” every time, and now you have to do it all over again. You don’t want to. There’s nothing more you can say, your batteries don’t hold much of a charge anymore, and you’re tired of going through it all. You wish you could just fast-forward right past the whole season.

You yearn for it because you know it’s your only shot. As lost and disconnected as you often feel inside, intellectually you know better and you’re still committed. You know this is your challenge, that everyone has something, and you need to make the most of this opportunity. Maybe this year really will be different. And even if it isn’t, maybe this year YOU will be different. You resolve to focus on what you can do and just accept whatever is out of your control. Like ever getting married and having a family.

You can’t say any of this out loud. The more fanatical members of your nation would write you off as a heretic. Everyone else would insist that you could get married if you really wanted to, or if you only followed their advice, or if you’d just stop being yourself already. They would tell you that you have no right to feel the way you feel, and certainly no right to complain. Some people REALLY have it bad. You can walk, you can see, etc. etc. You should be grateful for all the things you have.

You wonder if they are right. Maybe you’re just an ungrateful, self-absorbed idiot. You think about it and decide you’re not. You really are grateful that you can walk and see and everything else. Call you greedy, though, but you’d actually like a little more out of life, like someone to share it all with, a real home, a family of your own, and a normal place in the Jewish community. Is that so bad? Does the fact that some people are suffering worse make you a bum for hurting in your own way? Is it a competition? If you have a broken leg, is it supposed to hurt any less because the person next to you broke both his legs? Is your pain illegitimate because of that?

You hate Elul. You’re supposed to be feeling the awe of the coming Yomim Noraim, they haven’t even started yet, and already you can’t wait for them to be over. No way God likes what He sees when He’s looking at you now.

* * *

The first night of Selichos. It’s the middle of the night, the shul is packed, and the Chazan is belting it out in slow-motion. Now it’s real.

You spend the entire 45 minutes alternately trying to get into it, feeling guilty that you can’t get into it, and thinking that you shouldn’t think about it. You look around the shul. There’s no doubt that you are the only person who isn’t into it. You’re probably the only Jew in the world who isn’t into it. No wonder God keeps saying no. It’s the first night of Selichos! How could you not be into it?

After going way too slow, they finally reach the part where they go way too fast, and you find yourself rushing through the paragraphs. Now he’s singing the last Kaddish, everyone’s into it, then it’s all over. You feel like there was an opportunity to have all your sins cleaned away and all your prayers granted, and you just blew it. But you don’t think you could have done any better. So, basically, the game is fixed against you. But you know it isn’t. You really did the best you could, and that’s all God wants. Then again, of course you could have done better than THAT.

So your thoughts torment you. And it’s just the first night of Selichos.

* * *

It’s time to start figuring out where you will actually be for all the Yomim Tovim. This includes both where you will daven and where you will eat. It’s not about figuring out how to have the most uplifting and enjoyable Yom Tov. It’s about figuring out what will be the least painful and soul-depleting experience. It’s about balancing your religious obligations with your spiritual needs. It’s about balancing your obligations to family and friends who care about you and want you to spend time with them with your desire to run away from everyone and everything if only you had where to go.

There are no good options. Your singledom is the big elephant in every room you enter, even if no one makes a comment. You’re the older single person whose life didn’t turn out the way it was supposed to. You should be celebrating your kid’s Bar Mitzva but you can’t even get a good date – just like some of your nieces and nephews that you once diapered are now moaning about.

You don’t really fit in. The only thing that will change that is if you get married, but that seems increasingly unlikely. In the mean time, every Yom Tov meal with family will have a measure of subliminal discomfort by mere virtue of the fact that you are there. If they try to reassure you it will bother you. If they try to treat you normally it will bother you. Honestly, it doesn’t really matter what they do or don’t do, because the problem is really inside you. It’s not their fault you’re single. They love you. They want you to enjoy Yom Tov with them. It’s not their fault you can’t.

You realize that just as much as you are afraid of your family ruining your Yom Tov, you’re also afraid of your lousy attitude ruining THEIR Yom Tov. And you realize that they are probably worried about that, too. Because you’re single, and there is nothing they can say to reassure you, but they have to say something, only whatever they say will draw attention to your situation and hurt you more, but still they have to say something, and even if they give you a sincere, heartfelt blessing for the new year it will do nothing for you. You’re numb after all these years.

The other option is to stay home. Your local shul lets you know when they want money for something, but they couldn’t care less if you need some warm companionship for Yom Tov. You will receive a small number of invitations for meals and can eat the rest of them alone. You fret over whether this should be a “family” year or an “I’m an independent adult” year. Either way, you’re dreading it, you feel guilty for dreading it, and that only makes you dread it even more.

* * *

Succos is your least favorite Yom Tov of the year. It drives home all the ways your life is off track like no other holiday. Sitting in the succa should be an enjoyable, wholesome family experience. For you it’s just a burden – making a succa to enjoy by your lonesome, or being an appendage to someone else’s wholesome family experience. The main trauma of Pesach is limited to the seder; Succos is a constant knife through your emotional scar tissue for eight days.

Worst of all, Succos is billed as “the days of our joy”. Not your joy, that’s for sure. Every time you say a prayer related to the holiday you are reminded that you should be most happy during this time, which only makes you even more miserable. You can get into Rosh Hashana and Yom Kippur, but Succos is impossible. You would seriously consider trading eight days of Succos for one day of Tisha B’av. It’s no picnic, of course, but at least you can connect to the day and then it’s over.

Then there is Simchas Torah, which is your least favorite date of the year. Basically, any day which demands of you to be happy around your family and community makes you miserable. You don’t have a family and you don’t really have a community either, unless you can form one with other single rejects like you. The Torah provides abundant direction for how to celebrate the Yomim Tovim with your family and your community. It gives no direction whatsoever for how to enjoy them when you are deeply alone.

You love Judaism and you love the Torah. You really do. You just wish you could be part of it, not in some amorphous place trying to carve out a tolerable experience. Is that so terrible?

* * *

Finally, there are the inevitable set-ups. There are three times a year when amateur matchmakers (which include all the matchmakers in the world; there are no “professionals”) engage in this fine recreational pastime: the Yomim Noraim, Chanuka / winter break, and Pesach. The majority of dates older singles will have originate during these seasons, because that’s when everyone gets together and singles stick out the most.

It’s no coincidence that “wedding season” conveniently follows these three periods, a season from which you are always excluded. The Yomim Noraim is one of those times when matchmakers play the slot machines with singles, followed by celebrations for the lucky winners. You don’t know what’s worse, when eight people call you over a span of five days with suggestions, which leads to two blind dates that go nowhere, or when no one calls you at all. Is it better to be remembered and given more negative experiences or forgotten? Is it better to have had a faint chance at love and lost or never to have had a faint chance at all?

Either way, these days come and go without the faintest glimmer of a relationship, and you know it’s going to be a dry winter. There likely won’t be any more possible dates until winter break, when people are on vacation, singles are moving around, and the amateur matchmakers shuffle the deck once again. In the meantime, you will hear about people decades your junior celebrating their weddings and you will feel like a jerk for feeling too sorry for yourself to be happy for them.

* * *

The Yomim Noraim have come and gone. You tried really hard to connect, pray, return, and find inspiration.

You’re glad it’s over. And you wish it could have lasted just a bit longer.

Rabbi Chananya Weissman is the director and producer of Single Jewish Male, a documentary about the shidduch world. His most recent book, How to Not Get Married: Break These Rules and You Have a Chance, is available on Amazon and through the author. He can be contacted at

About the Author
Rabbi Chananya Weissman is the founder of EndTheMadness and the author of seven books, including “Go Up Like a Wall” and “How to Not Get Married: Break these rules and you have a chance”. Many of his writings are available at He is also the director and producer of a documentary on the shidduch world, Single Jewish Male, and The Shidduch Chronicles, available on YouTube. He can be contacted at
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