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Dating Maze #359: Wild Past
Dating Advice 359

Dating Maze #359: Wild Past

I feel guilty about my past escapades. Should I tell him about it?


Dear Rosie & Sherry,

I'm in my late-20s and have been maturing spiritually. I started going to synagogue, eating kosher food, and even spent six weeks studying in Israel. I decided to stop dating until I was really sure about the direction I wanted my life to take and to feel more comfortable about who I was becoming.

Recently, I decided that I was ready to find the right one to marry. Two months ago, I started dating someone who wanted the same things as I – lots of kids, a home filled with love of Judaism, a close-knit community. We both even work in similar fields! Fortunately, we got along well from the start and enjoy spending time together – going for coffee, picnics, museums, hikes, and an occasional concert.

I can really see this leading to something permanent. But I am terrified about letting him know a few things about my past. In college and through my mid-20s I was very into the party lifestyle – getting drunk, wild and promiscuous. Looking back, I feel guilty and embarrassed about some of the things I did.

I'm worried that these experiences won't go over too well with the man I'm dating. He’s led a pretty sheltered life and the only dating he's ever done is for marriage. I'm afraid that if he hears about what I did in the past he'll think less of me as a person.

Does my past matter? I could live without saying anything about it, but what if he asks? I can't just lie! Also, if we do decide to get married, should I tell him the whole gruesome story?


Dear Melanie,

You've asked a question that becomes an issue for many people who decide to date seriously for marriage. Many of them have regrets about lifestyle choices from their younger days, and wonder if they should tell it all to the person they want to marry. They may feel it's important to be completely open with their future life partner, or they may feel guilty about what they did and believe that revealing the secret serves as an atonement.

It is counterproductive to intentionally withhold important information.

No matter what motivates you to "come clean" about the past, volunteering this information is a terrible idea. We're not saying this because you should be hiding information about yourself in order to get married. To the contrary, it is counterproductive (and/or dishonest) to intentionally withhold important information, or when a couple fails to discuss viewpoints and issues before becoming engaged.

Here’s the rule: When a dating relationship seems to be leading in the direction of marriage, there is an obligation to reveal and discuss matters that are likely to have an effect on a couple's life together, even if they are embarrassing or unpleasant. This is the only way that both people can make an informed decision about marriage. Some of this information includes:

  • current medical conditions (and prior conditions that may reoccur)
  • current debts and other financial obligations
  • mental health conditions such as anxiety or mood disorders and anything requiring medications
  • current or prior substance abuse or addictions
  • financial and personal responsibilities to children and spouses from past marriages

Notice that this list does not include details of prior romantic encounters. First of all, these don't have the same effect on a marriage as those we've listed. Most importantly, though, such disclosures invariably harm the person who hears them and can damage the relationship itself.

How can they be harmful? Intimate details of a past relationship can cause the listener to form a visual image of what occurred. The picture that forms in their mind can interfere with their thoughts and feelings about the current relationship, and create a barrier that may be difficult moving past.

The man you are dating will probably not be surprised to learn that you went to wild drunken parties. Contemporary secular culture accepts these choices. Most people aren't troubled by the unspoken knowledge, or assumption, that young secular people engage in an active social life. However, when they actually hear the details, they can get stuck on them.

That's why it’s not a good idea to volunteer this information. He knows you had a “non-sheltered” upbringing, and you don't need to tell him anything more. If he asks about your prior sexual experience, you can answer honestly without going into details. "Yes, this isn't my first relationship." You can add, "That was a different part of my life and it doesn't reflect who I am any more. It's something I have moved past."

Don't offer names, numbers, or other details – even if he asks for them. In our decades of working with dating and married couples, we can testify that – without exception – everyone who asked for details later regretted hearing them. This harms a relationship in the precise way we've described. Instead of giving details, you can explain that this is a part of your life that you don't like to think about, and that it doesn't have a connection to the future you hope to build together.

Dealing with Guilt

We've answered your question about when, if, and how to tell this man about your past. Now we’d like to help you find a healthier way to deal with your own feelings about your earlier life choices. Right now, you're disgusted and embarrassed about what you've done. That's a common reaction for someone whose worldview has changed because she's matured and chosen a more conservative lifestyle.

When we undergo this process of regret, we become a changed person.

The Jewish concept of teshuva ("return") is a process of regretting certain things we did in the past, asking God for forgiveness, and committing not to do them in the future. The essence of teshuva is that when we undergo this process, we become a changed person. We're not the same person we were before. This is one of the great gifts the Almighty gives us – the ability to sincerely regret, forgive ourselves, be forgiven, and wipe the slate clean.

Teshuva is actually an ongoing, lifelong process in which we continually try to be better people and renew ourselves. Sometimes the leap forward is large and dramatic; sometimes it is small and imperceptible. If you can look at yourself as someone who has grown beyond who you were in the past, you can stop fixating on prior mistakes and concentrate on being proud of your growth and forward movement in life.

It can be difficult to make a transition from the type of social dating you engaged in before to the goal-focused dating for marriage you are now choosing. We believe you'll find it helpful to develop a mentoring relationship with someone who is experienced in your age category and life choices. A mentor can help you know what issues to expect, what to look for and talk about as you become serious with each other, and how to know that you've met the right person to marry.

We wish you success in navigating the dating maze,

Rosie & Sherry

May 26, 2012

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Visitor Comments: 39

(31) Magda, October 14, 2013 6:40 AM

Just Be Honest

Dear Melanie,
I would believe you wouldn't want your boyfriend know about your past from someone else. That was exactly what I have gone through at my last dating.
I was lucky that my boyfriend was just a real great man in my eyes and I had all the courage I need to tell him about my past. He accepted me the way I am.
We were just so good to each other. But it could be just my fate that he recently "departed" and left me alone.
G-d bless!!

(30) Anonymous, October 13, 2013 7:11 PM


Many years before I married my wonderful husband, I kept company with people I'd have nothing to do with today. Promiscuity was barely a concept, let alone something to be avoided. My Jewish soul suffered from ignorance of what was good or bad for me, and I had a breakdown. Years later I became a ba’alas t’shuvah, firmly observant, with mentors helping me face, deal with, and reconcile past behavior. They ushered me into a good, rich, truly Jewish life. My husband comes from a more innocent background, yet certainly knows that the secular world condones and even expects pre-marital relations. Does he know I have a history? Well, yes, as I was married at one point. Have I been specific about the rest of it? Not on your life. We have a ten-year-old marriage that is better than anything I'd have imagined possible; there would be no upside in revealing unsavory details. The results would be sadness on his part, and embarrassment on mine. Were he to ask outright (which he wouldn’t), I’d say that yes, there were men in my life – and that would be IT. The person he married is simply not that ill-informed girl of years ago. Don’t feel you have to spill your guts to your chosson or husband. See a therapist or psychologist for that, don’t burden your marriage with gory details, and go live your wholesome, happy life.

(29) Aaron, August 28, 2013 10:18 PM

No purpose in divulging is Loshon Hara against oneself

Rabbi Avigdor Miller, zt"l in his famous Marriage Tape (CD?) no. 620, says one should NOT talk about past discretions when dating. Rather, he says, one should sell oneself and say the very good qualities you have or those in your family.
Good advice from a wise man!

(28) Joshua, August 26, 2013 11:43 AM

Halachis ramifictions

I do not think Rosie and Sherry were correct as far as you do not have to tell whether you'd had past sexual experiences to your chosson. As far as i know a chosson has the right to know whether this is going to be the first relationship or not. Yes, one should not never go into details about her sexual encouters.
I would encourage you to speak to a reputable Halachis authority who can advise you when and how to reveal this issue. Hatzlochah!

(27) Anonymous, August 1, 2012 3:24 PM

Personal Experience!

I dealt with this exact problem. I was a bit of a wild child to say the least, and my husband was the complete opposite. That is okay! I was honest and forthcoming about it because while those things were in my past and he is my present/future, those actions affected who I became. Good or bad, I cannot hide them, for the mistakes or actions I made helped me grow to a point where I was mature enough to be married. Being more religious or not is a cop out. When we marry, we become one soul, all past mistakes are forgiven and we look to the future. Who someone used to be does not matter, its who they are now that is most important. My marriage is built on pure open trust. I would not have been able to share that with my husband if it wasn't. I am lucky to have such a wonderful relationship, but I told him when we first dated that I was only interested in full honesty for everything. Yes, sometimes it might hurt, but if you discuss what about the honesty hurts, then it no longer becomes a barrier. Only by not address issues does our past taint the relationship. If it something he cannot handle, then he does not understand the Kabbalat Panim and the journey you will be on.

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