Category Archives: Dear Chana

Helpful Tips in the Process of Teshuva – New and Revised

Dear Chana

I know you are very good with real hands- on ideas / tips and tools in facilitating life/ Torah truths.

I have a question about teshuva. If a person is trying to do teshuva and gets caught and stuck on one of the stages of it [ ie: has stopped the sin – but can’t bring oneself to regret it enough or doesn’t feel that they can declare for the future that they won’t do it again, etc.] what are some practical ways to motivate oneself to continue in the teshuva. Also if one in fact accomplished teshuva, how can one really stay in it and stick to it?

Thanking you in advance for this important info that I have been grappling with. Name and Seminary withheld by request

Dear JemSem Reader

Thank you for asking such vital questions! Teshuva is something that is one of the most special gifts that Hashem has given us in this world. To have messed up and be given the opportunity to erase the wrong or even to turn it into a zechus for ourselves – is almost beyond our imagination, it is such a gorgeous example of Hashems’ chesed and rachamim!

I want to quote from the Me’eri:

“From the time that one commits to repent, even if the actual realization of that commitment is a long and difficult process, his status immediately changes upon the commitment and he is already called a Chassid”

Doing teshuva is a privilege and one should be b’simcha when going through the process because one can get closer to Hashem!

It is also clear from the sefarim, that if a person did teshuva [honest and real teshuva] – but eventually ended up sinning again, their 1st teshuva is not ‘taken away’ – it still stands for them and is a zechus for them in some way, but, of course, they must start over and do teshuva again. They must go the the process fully and completely and work hard to really make it stick this time. The Rambam in Hilchos Teshuva tells us that teshuva helps for absolutely everything, anytime, not only during Rosh Hashanah and Yom Kippor, but at any point of the year. So a person should never feel disheartened that they have sunk so low as to never be able to accomplish it. They can do teshuva at any point in their life, and it will always help on a myriad of levels, no matter what they have done, to bring them back closer and connected to Hashem.

Here are some pointers for both trying to actualize and continue on with the process of teshuva and also how to stick with it and not repeat the sin:

• Learn about it. See the sin in black on white – of what the Torah says about the aveira. Not only Torah sources – but get English Judaica books on the subject, as well as download shiurim on the subject. The more you see and hear about it, the more of an impression it will make on you.

• Think!! Doing teshuva takes an intellectual honesty and an emotional maturity. Try to bring home to yourself the importance of life in this world, what we are doing here, the concept of sechar v’onesh, and following Hashem’s Will.

• Daven: Hashem wants us to turn to Him, right? We can’t ‘pull the wool over His eyes’ – He knows exactly where we are at. So ask Him for help in whatever stage you are up to. [to stop the sin, regret, or to not repeat the sin, etc] We actually can’t accomplish teshuva or anything for that matter without Hashem’s help. Formal – in shemona esria or Tehillim [ specifically 32, 39, 51, 90, 146] and informal tefillah – talk to Him.

• Make boundaries: You had a weakness in this area, so don’t tempt yourself. Build fences around it. This takes thought. You may want to reconsider who you hang out with, where you go, things that you are doing. Like with dieting, teshuva is not a quick fix, but it is a change in lifestyle. Things that help teshuva to be accepted:

1. Seek out ways to increase your acts of chesed and help others.

2. Become an even bigger seeker of truth, and to live your life in a straight and directional way.

3. Really go for mitzvos asai, accomplish them them with great simcha and kavana, work hard to stay away from mitzvos lo sa’asei.

4. Give Tzekaka. It saves a person on many levels.

5. Help motivate others to the ways of teshuva.

6. Say omein in kaddish and answering Yehai shmei Rabba – in a voice with kavanah, is a really big deal and creates many zechuyos for a person. Always.

7. Learn the specifics of hilchos Shabbos. Keep is meticulously. Become a person who is knowledgeable and careful in this.

8. Kol ha’ma’aveir al midosov, mochlin lo al kol p’sha’aav. Whoever was wronged and chooses to overlook it – and not be bothered by it, Hashem forgives them for all of their sins. [a biggy!]

This is a worthy topic indeed! Teshuva can be achieved at any point during the year it does not have to be only connected to the Yamim Noraim.

Hatzlacha Rabba!!



Iyar 5775 – Weighty Matters – Part I

Dear Chana,

I am a twenty years old and I was thinking of starting to date. I was appalled when numerous people informed me that I shouldn’t bother because I am somewhat overweight. I was told that guys have so many options in dating that they automatically discard anyone who is heavy. I find this quite disturbing. Is it true that all guys are so totally into a girls looks and weight? Should I really put off dating until I fit into the standards of society? [pun intended!]

Thanks in advance for the clarity that I know your answer will bring!

Name and seminary withheld upon request

Dear JemSem Reader,

Thank you for bringing this question to the forefront! This is a topic that is not usually discussed openly, and I am happy that you have asked it. The issue of weight is a delicate and sensitive one whether it has to do with dating or not.

I would like to first discuss weight as a health issue from a practical and hashkafa perspective. G-d willing I will discuss the ramification of shidduchim in next months [Tishrei} JemSem issue.

Our challenge is to find a healthy balance when it comes to taking care of our weight. On the one hand, a fixation with thinness can be not only unhealthy but
dangerous. Worshipping the gods of thinness can lead to anorexia and bulimia. These are serious diseases that if gone unchecked can be fatal.  On the other hand, eating obsessively leads to obesity and a host of health issues. The solution is obvious –  a person must find a healthy balance for herself. In practice this is not easy. The first steps we must take is to learn how to be healthy with balanced nutrition and excercise. This involves reading the right material [there is
so much information today on these topics!] and perhaps going to a nutritionist. The second step is to have the willpower to follow through with what we have learned. This means to follow the diet that fits our lifestyle and get to aerobic, kickboxing, step, taebo, strength training, body sculping, zumba, circuit training classes. Do what you enjoy, and learn to have fun with it, but the key idea is to get out there and move!

I would like to stress that this is a halachik issue and not just an issue of health and aesthetics. The Torah commands “V’nishmartem me’od l’nafshoseichem” [Devarim 4-15]. We are obligated to guard the amazing life and the wonderous body that Hashem has so graciously given us.

The Rambam in Hilchos Dei’os devotes a whole  perek to food, what to eat and what not to eat. He says that most types of illness are caused by eating either the wrong foods or eating too much in general. Furthermore, the Rambam also informs us in Hilchos Dei’os that we are obligated ” laida es Hashem” – to know Hashem in every way possible – even outside the realm of mitzvos. In other words, there is a way to connect to Hashem all of the time, no matter what we are doing. This is hashkafically intuitive. We  only live a limited amount of time on this earth and there must be a way to continuously be building a relationship with Hashem.

Hence the obligation to be healthy. Through getting the right amount of sleep, eating right and excercising – we will be able to serve Hashem all the time
to the best of our abilities. We will feel good, feel more fit, and be able to take care of the wonderful gift of our body that Hashem has loaned us. It will also add to our self esteem and happiness. It is really a terrifically special feeling to know that you are helping yourself to be as healthy as possible.

So being a couch potato and eating badly doesn’t help anyone physically or emotionally and is in a sense antithetical to Torah. Food for thought!

To be continued next month with this topic connected to shidduchim…………

With Warmest Wishes,


Teves 5771 – Dating Queries

Dating Queries Teves 5771
Dating Queries
by Mrs. Chana Silver


Dear Chana,

Can you please give your opinion about several dating issues? I have been having debates with my friends about these important things – and we really need to get some clarity about it – because they come up all the time.

Is a second date a must – every time? What is considered normal as far as spacing the dates? How do you advise people about phone conversations during dating? What is your take about texting while dating?

Looking forward to hearing from you!

Thank you so much for Jemsem – it is such a valuable site!
Michlalah 5770

Dear JemSem Reader,

Thanks for bringing up these important issues! They certainly are part and parcel of dating situations – and do need clarity. What I write – is obviously my personal opinion based on my experience, you may hear other answers to these questions, as how to go about these things is not absolutely etched in stone.

A Second Date??
Here’s the basic outlook on this all important question: Do I go out with him again? If the first date was good, obviously you’ll go out again! If the 1st date was pareve, just okay, no great shakes, it wouldn’t bother you never to see him again, go out anyway!

If the 1st date didn’t go well, you need to analyze why. If it was because of something your date said that doesn’t jive with you, or an attitude, hashkafah, behavior, or language that was used, you need to speak to the shadchan and find out if that really reflects who the person is. If it does, don’t go out again. Otherwise, give it a second chance.

Many times people aren’t themselves on 1st dates. Let’s face it: a first date is a blind date. You’re strangers to each other. In most circumstances it takes people time to warm up and open up. Many make the mistake of feeling that they totally ‘know’ the person after the 1st date and that they are sure this person is not for them. As a matter of fact, most people tell me that they are shy when first meeting people and they when they feel more comfortable, they become more outgoing. So be careful not to nip a viable situation too quickly in the bud.

Spacing the Dates
Don’t let a lot of time elapse between your 1st and 2nd date; you don’t know the person yet and there isn’t all that much to consider. A day or two perhaps. After that, the usual is about twice a week or so.

There is a concept of momentum. Once the process starts to take off, you want to keep it rolling. Too much of a break could make it feel like you are starting over each time. On the other hand, you must have time to think in between the dates, this is also very important.

Ilana* and Chaim* had a whirlwind dating adventure that was very exciting and thrilling, and everything seemed great. They went out often, and when they weren’t together, they spent a lot of time of on the phone with each other.[more on this in the next section] The day soon came when Chaim popped the big question, and, of course, Ilana said yes. They had a l’chaim and a vort, set the date for the wedding, and began making life plans. It was then that Ilana started to notice certain things about Chaim that bothered her. Things he said and ways he acted that didn’t sit well with her. After some soul searching on her part and some meaningful talks with key people in her life, she broke the engagement.

Ilana openly tells people now that had she done all this in a more serious fashion when she was dating – speaking to key people and having time to think in-between dates – she would have seen these red flags more consciously and would not have gotten engaged. These things were in fact tugging on her somewhat, but she kept putting them on the back burner because things seemed so good. It was all happening so fast, and Chaim was always there, either in person or on the phone.

This is a decision that will have an impact on the rest of your life. So make sure to have the time you need to think things through and talk it over with that significant person who is helping you, while still keeping it at a good pace.

On the Phone
Stay away from long phone conversations. The phone should be used as a pleasant bridge between dates to keep the relationship running. The conversations should be on the shorter end; deep and important issues should be discussed in person. The reason for this is that a couple can develop a ‘phone relationship’ – and hide behind the phone or a computer for that matter, and this is quite different from relating to the person directly – face to face.

Though texting is ok for quick hellos or short messages, and it is quite convenient, too much texting daily is not emotionally healthy. It is short, choppy, and shallow. People today feel that they are building deep connections through texting and computers etc., but they are not. Perhaps several texts a day back and forth could be appropriate, more than this, is just silly, a waste of time, and foolish. There is nothing at all that can take the place of being with the person and getting to know them for real.

Thanks again for being the conduit for me bringing out these important and ubiquitous dating issue!

With Warmest Wishes,


Shevat 5771 – Dating Life Issues: What To Factor In – What To Filter Out – Part 1

Dating Life Issues: What To Factor In  -  What To Filter Out - Part 1 Shevat 5771
Dating Life Issues: What To Factor In – What To Filter Out – Part 1
by Mrs. Chana Silver


Dear Chana

I have heard so many differing and confusing opinions about family issues/ divorce/ shalom bayis problems / physchological conditions/ and physical illness concerning shidduchim. In your opinion how should one go about it all? It seems so daunting when there are issues! Can you break down some of the ideas and the how tos involved and give some advice about them? How important do you think these things are?

Jemsem is so full of great info! Thank you!
Midreshet Tehillah

Dear Jemsem Reader,

Wow what a whopping important question! There are many issues that transpire in the dating world and a myriad of questions that arise about how to travel the highways of shidduchim.

It’s important to know that seldom does a person find a ‘storybook’ situation to marry into. There is always something in one area or another, a skeleton here, a predicament there.

I have found that in the shidduch world people are too quick to reject, abandon, and discard a potential idea because of these situations, and this should not necessarily be so.


Unfortunately, in today’s world there are divorces, families with much discord, dysfunctional relationships within the clan, and problems that take on many different shapes and forms in the household.

For some, these kind of family issues are not what they want; others can make peace with them.

Here are some steps to take:


Ask about it from all angles. Speak to the Rabbanim who have been involved with the family. Find out the particulars and what exactly has gone on and what is currently going on. Make sure you speak with people who truly know the facts. Talk specifically with the boy’s Rebbi who knows him well. Find out about their emotional history and if the Rebbi feels that the boy is emotionally stable. Ask them if they see any manifestations of deeper issues going on, in general, and based on the particular family issue that you are checking into.


Tell him the details of the situation and hear what he has to say. Listen carefully to the advice that he has for you. Rabbanim have much experience in these matters, and they are certainly there to guide us.

3] THINK!!

You have to figure out if you feel you can handle a circumstance like this. Think about the future. Whatever the nature of the problem, what will Shabbos, Yom Tov, family simchas be like? Will you be able to be supportive of your spouse? How will this issue possibly affect your children? Obviously, you can’t fully know the answers to these questions, but how do you feel about it now?

What if someone went to therapy to help them iron out family difficulties and life events? That’s a terrific thing! After all, think of the alternative! These people were trying to help themselves and move past their issues. It really shouldn’t be such a stigma.

Tamar* grew up in a highly dysfunctional family. When she was fifteen, her parents got divorced and she had to face the additional difficulties and stresses that came with that. When she was eighteen and in seminary in Israel, Tamar decided that not only did she want to get her hashkafic and Jewsh self together, but that she needed to complete the circle and deal with her emotional and personal self. She was in therapy for awhile and she made great headway. Today she is an emotionally healthy and stable young woman who is married and functionally raising a beautiful family. Where would she be without the therapy?

Perhaps you can reframe that fairytale image that you had conjured up and decide that this will work for you, or you may feel that this situation is just not what you want to be part of.

If you have thought this all out and done your checking etc – and you are already dating the person, one of the most important concepts is to analyze deeply about this person and your budding relationship with him. If he is stable, and you are building a great foundation and connection, and if you respect him and are communicating well with him – well, these things count a lot.

Thanks for allowing me to bring out these very important ideas!


With Warmest Wishes,


Adar I 5771 – Dating Life Issues: What To Factor In – What To Filter Out – Part 2

Dating Life Issues: What To Factor In  -  What To Filter Out - Part 2 Adar I 5771
Dating Life Issues: What To Factor In – What To Filter Out – Part 2
by Mrs. Chana Silver


Dear Chana

I have heard so many differing and confusing opinions about family issues / divorce / shalom bayis problems / psychological conditions / and physical illness concerning shidduchim. In your opinion how should one go about it all? It seems so daunting when there are issues! Can you break down some of the ideas and the how tos involved and give some advice about them? How important do you think these things are?

Jemsem is so full of great info! Thank you!
Midreshet Tehillah

Dear Jemsem Reader,

Last month we dealt with family issues which included divorce and shalom bayis, and now we will speak about psychological condition.

Psychological Conditions:

There are many different forms and degrees of psychological conditions – depression, bipolar, ADD, and ADHD, to name a few. What are the guidelines with some of these things?

You need to find out the following:

– Does the person have a therapist?

– Is he currently dealing with the problem?

– Is the psychological condition chronic or episodic?

– Was the person on medication in the past? Is he currently taking medication?

– Is the medication long- term? What are the side affects? Will this medication affect the future?

– Is this person willing for you to talk with his therapist?

– Where mild or severe is his case?

– How does it manifest and affect his life?

You may want to talk to a psychologist or psychiatrist to help you understand the problem better, or perhaps, to research it yourself. Each case is individual and very different. Some situations may be quite serious and significant – and be a no go. Other situations may not be as big a deal and with the availability of medications and treatments, the person may be highly functional and very capable of carrying a meaningful, deep, and fulfilling relationship. It’s possible that because of his difficulties, he is an even deeper and more sensitive person, maybe even more emotionally aware than other might me.

As before, speak to a Rav about your finding, and get in touch with your own feelings regarding this.

Next month – we’ll deal with physical illness.

Continued thanks for bringing out these all important things!

With Warmest Wishes,