How much time does it take to be “ready”? Each individual is unique and how much time is needed to heal can vary. Much also depends on how long the marriage lasted and the reason for the divorce.

“Don’t rush” stresses Sherry Zimmerman a dating mentor and therapist who has worked extensively with singles. “It’s better to delay dating than to experience a rebound relationship which seldom lasts.”

It can take months or even years before a person who has divorced can be ready to enter the parshah for a second time according to Ruchama Zions who has been working with divorced men and women for the past 16 years in Yerushalayim. “That said not everybody needs such a long waiting period ” says Ruchama. “A woman who was already focused on developing better skills and self-awareness might be ready to begin dating immediately after she receives her get. It’s very individual.”

Pessy whose son Yudi got divorced after a year of marriage says that her son had a rav who helped him overcome the trauma of his divorce. “In all the pain and tragedy of the divorce my son’s relationship with this rav was a real gift ” says Pessy. “Yudi was ready to resume dating fairly quickly in large part because of the support he received from the rav.”

As a general rule shadchanim dating coaches and therapists agree that men and women must ensure that they’re in a healthy place before starting to date again. “Divorce is traumatic and it’s important to deal with the issues that arise as a result ” says Ruchama. “Sometimes one feels he or she was the innocent party who was wronged in the previous marriage and therefore they have nothing to work on. But that’s simply not true. Perhaps she wasn’t assertive enough or maybe the boy needs to improve his communication skills.”

Dini for one struggled with being assertive in her first marriage. “I think if girls are encouraged to be assertive when making decisions they’ll gain the confidence to be assertive in their dating relationships. That would’ve been beneficial to me. Girls should never be afraid to speak up and ask questions when necessary ” she says. Therapy helped Dini process the swell of emotions she felt post-divorce: “I still feel a lot of anger toward my ex which I need to work through before I can manage a healthy relationship with someone else.”

With therapy you can “figure out what happened in your first marriage — and why ” says Rosie Einhorn LCSW. The process can also open the door to self-discovery. “Before considering remarriage a person must get to know themselves. It’s important to know where you’re going before dating again ” Rosie says.

Rikki was married for 14 months when she realized that divorce was unavoidable: Her husband had suicidal tendencies and suffered from extreme mood swings. “I felt like I was floundering in quicksand and could never feel secure or safe,” she says. After receiving a get, Rikki spent six months in therapy to both heal from the trauma of her failed marriage and to work through any issues that might get in the way of a future shidduch.

A common obstacle to successful chapter-two dating is lack of trust in oneself. “A lot of divorced people second-guess themselves, wondering if they’ll ‘mess up’ again,” say Esther Williams, who directs Shalom Task Force in New York. “Teaching people to trust themselves again is crucial. One way to solidify their shaky confidence is to validate their emotional intelligence and show them where they demonstrated good skills or made good choices,” she says. “You want to help singles define what a healthy relationship looks like.”

Rochel Goldbaum, a dating coach and speaker, offers dating workshops at the annual Sister to Sister Shabbos event, which is attended by over 450 divorced women. “I view my main role as dating mentor to help women to learn to trust themselves again,” she says.

According to Rochel, there are two issues that get in the way of what a person really feels: fear and image. Of the women she personally coaches, she estimates that 60 percent have a fear of marriage. “You have to want marriage more than you’re afraid of it,” she emphasizes in her conversations with women. She tries to normalize the fear by having the women learn how to accept it. “This process is essential to master before resuming dating,” says Rochel.

To help “second-time” daters conquer their fears, Rochel begins her workshop with the same message every year: “Who do you think is more equipped for marriage? The 18- or 19-year-old girl you were at your first marriage, or the 28-, 29-, or 30-year-old you are now?” She challenges the women to realize that their added maturity and experience has qualified them to date smarter this time. “A woman almost never falls into the same situation again,” Rochel claims with conviction. “She can almost smell the problem and knows to avoid it this time.”

As for image issues, Rochel asserts that “We struggle with this on a daily basis, worrying so much about what the world thinks of us. We’re so anxious to receive approval from others, especially in areas like height, looks, job status, and family background. It’s important to overcome the worry of what people will say — such as, ‘After all these years, this is the best you could do?’ ”

Because chapter-two dating can bring up so many issues, Rochel stresses the importance of having a mentor to clarify feelings with. “It’s crucial to have someone who can be completely objective about the dating. The mentor should not be the shadchan, parents, or anyone with an agenda,” she says.

Ruchama finds that a large part of her work includes supporting and guiding parents of daters, as there can frequently be a gap between what the parents and the singles are looking for the second time around. “It can happen that the first time, the girl wanted a full-time learner. Now, she’s interested in a working boy. The parents aren’t always in agreement or even aware of what their daughter is searching for. She changed her priorities, but her parents haven’t.”

After divorce, newfound singles often consider good middos above everything else. “Some people might have focused on yichus or other things the first time around. Now they realize what truly counts,” says Leah. The girl who previously was only looking for the future rosh yeshivah is now searching for a mensch. The boy who might have been interested in a wealthy and chashuve family has now decided that the girl’s character is of paramount importance.

First Date, Take Two

When Leah’s daughter Chedva got married straight out of seminary, there was a sense of urgency and frenzy. Not so the second time around. When divorced singles reenter the dating parshah, “they proceed more warily,” says Leah. “The dating time is longer because everything is examined more closely. Every comment and nuance is scrutinized carefully. Because of their past experience, they aren’t going to just jump into something.”

Since divorced singles are naturally cautious, they often need more time to decide if the person is right for them. There’s no yardstick for how long the dating time should be, but as a general rule, Sherry advises singles to “date for enough time to see what kind of person he or she is. Is the person thoughtful? Generous? Responsible?”

According to Yudi, dating longer and getting to know the other person well isn’t just a good idea, it’s critical. “The first time around, I just assumed that everyone who dated really wanted to get married. Unfortunately, my ex-wife felt social pressure to marry at an age that was socially acceptable in our circles. The reality was that she didn’t want to be married — to me or anyone else. She resented being married and felt bitter about the expectations chareidi culture placed on her. I learned the hard way to make sure that both sides really want all the responsibilities and commitments marriage entails.”

The longer you date someone, the more you’ll see the different shades of his personality emerge. “The dating should include different venues and experiences because it’s essential to see the other person in diverse circumstances,” Ruchama advises. “For instance, travel by bus or train together. You want to see how your date conducts himself.”

Rosie says to her clients, “You’re smarter this time. Put on your glasses and really see the person. See him in different situations and establish whether he is who he says or thinks he really is.”

As important as scrutiny may be, Rochel stresses that you cannot judge someone and create a relationship at the same time. She advises women to relax and enjoy their dates and to be present in the moment. “Your job while on the date is to create a friendship, not to judge every nuance of every comment and action. Later, when you get home, you can connect with a mentor and analyze the date.”

Though more dating time may be necessary in chapter-two shidduchim, there should be a healthy progressive process. “Dating productively means not getting stuck at any point. It’s one step at a time, but the goal is always upward movement,” says Rochel.

When Rochel coaches daters, she tells them to wipe out the image in their mind of what they’re looking for, since it’s most likely imaginary. “People want to make a kind of Mr. Potato Head — they want ‘this’ like their brother-in-law and ‘that’ like their father, and not ‘this’ like their ex. But this depiction doesn’t exist and it’s damaging to create such an image,” she explains.

Instead, Rochel asks singles to picture a blank screen with zero images. “Date the way Hashem created the world. ‘V’haaretz hosah sohu v’vohu.’ The objective is to create a blank screen; otherwise one can end up comparing each of his or her dates with this imaginary paragon, which is obviously problematic.”

Rochel also cautions divorcיes against making unhelpful comparisons between their ex-husband and the man they’re dating now. “Sometimes women will say, ‘My ex had glasses and this man has glasses —uh oh!’ Constantly looking back and comparing is not constructive.”

Digging into the Past

When Rikki started dating again, most of the suggestions she received were young men who had also been divorced. Investigating the names took on an FBI-like quality, since histories were much more complicated now, both for her and the young men who were suggested.

Digging into the past to find out about a failed marriage is no simple feat. “From a halachic perspective,” Rabbi Yitzchak Breitowitz, Rav of Kehillas Ohr Somayach in Yerushalayim, notes that “Obviously, divorce always raises a red flag and prospective shidduchim will be very concerned and will want to know all sorts of details.

“On one hand, if the divorced party was clearly the victim of improper or deceptive behavior, he or she should and must have the right to clear their name and reestablish their good name. On the other hand, there are strong issurim of lashon hara and halbanas panim that must be observed.

“I’d suggest that the person fully discuss their difficulties with a trusted rav who will then have all the facts,” continues Rabbi Breitowitz. “When a shadchan or a date inquires as to the reasons for the divorce, the response should be, ‘Obviously, I have my particular understanding of why our marriage broke up but I think you should talk with Rabbi or Rebbetzin X, who can give you the details that will help you understand my situation.’ ” Rabbi Breitowitz adds that he would apply this formula to virtually every circumstance.

“It’s almost impossible to really discover what happened in the previous marriage,” Ruchama notes. Though there are no guarantees that you’ll ever discover the true reason for the divorce, it’s nevertheless important to keep asking questions, Rosie maintains. “Don’t just call the references. Try to find out what triggered the divorce. Speak to neighbors, friends, and teachers. If you’re told that they divorced because they weren’t suitable, dig a little deeper. ‘In what way weren’t they a match?’ Speak to as many people as you can to get a full picture.” Rosie advises people to do whatever is humanly possible, but then to daven — and daven some more.

As a shadchan, Kaila is in a unique position because she’s often privy to private information about both parties. “I try not to be judgmental and will not take sides,” she says. “I also don’t dig into a divorced person’s past. I ask for references so that any prospective match can do thorough research. I do ask if they have a mentor or therapist that they speak to, as any divorce, no matter how clean, leaves its scars. I try to keep the interview light; the questions come out of curiosity to find out more about the person in front of me, not as an interrogation.”

Ruchama likewise avoids asking divorced singles about their stories. “Each side has its own perception of what happened and it’s not productive to ask the divorced party for details,” she maintains. Instead, she speaks to singles about their marriage goals and what’s most valuable to them in a relationship. She advises people who are seeking information to focus on middos. “It’s more constructive to speak to friends, neighbors, work colleagues, and people who knew the person before the marriage to clarify personality and character.”

As mothers of divorced children, Pessy and Leah both assert that it’s not helpful to speak about the other side. “I have my point of view and they have their point of view, and the truth might be somewhere in the middle,” says Leah. Their advice: If someone is looking for information about a person’s previous marriage, speak to a rav who was involved in the divorce.

In most instances, families on either side of a divorce are usually not reliable reporters — they’re biased and emotional and are unlikely to paint an objective picture. Because of this, “there should be some external reliable source such as a rav, rebbetzin, or even a therapist, though in that case, a waiver of confidentiality needs to be obtained,” says Rabbi Breitowitz.

How should a shadchan handle inquiries into a previous marriage? According to Rabbi Breitowitz, questions should be posed directly to the rav involved, but if necessary, the shadchan should honestly disclose the difficulties that he or she perceives. It’s essential, however, to try to balance that with the good qualities as well. “Be positive but be truthful,” Rabbi Breitowitz warns. “The same is true for anyone who is approached for information. Tell the truth, but do not exaggerate. It’s important to give a balanced report.”

Despite the complications that arise when dating after divorce, many people are granted a second chance at happiness. “I’ve seen many couples remarry and go on to have successful marriages,” says Ruchama.

Adina is a case in point. It took two years for her to realize that her first marriage was a terrible mistake. “I thought I’d be the perfect wife and have the perfect, storybook marriage. You know, ‘and they lived happily ever after…’ Adina admits. “I couldn’t deal with facing the truth that this idyllic picture and the reality didn’t match.”

The healing process was long and complex for Adina, but she eventually started dating again and met her true match, with whom she has built a loving marriage. “There was a lot that I needed to learn before I could become that ‘perfect wife’ that I had dreamed about. I had a tremendous amount of growing to do before I was ready to build a relationship with someone else.”

The huge epidemic of early divorces we see today in our communities is both a curse and perhaps somewhat of a blessing, says Ruchama. A curse, since a number of those marriages might have been salvageable, given the proper means and direction. And the blessing? “Perhaps in the past a person would have remained in an unhappy marriage because the stigma of divorce was so great,” says Ruchama. “Today, with a lot of siyata d’Shmaya, it’s entirely possible for divorced men and women to thrive in rewarding second marriages.”

Mrs. Sheila Segal is a dating and relationship coach who coaches internationally. She also offers shalom bayis workshops for women.

(Originally featured in Family First Issue 574)