12 Things to Know About Dating the Second Time Around
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12 Things to Know About Dating the Second Time Around

12 Things to Know About Dating the Second Time Around

My lessons in dating after divorce.

by

1. Set in Stone

Somehow when we were teenagers and dating for the first time, everything about our life was flexible. We could pick up and relocate, switch jobs, date someone without a job, and be carefree about future plans. Now after having had children and spouses, we can’t relocate, our jobs are fixed, the way we parent our kids is set, and there isn’t much flexibility. People either fit into your life as it is now or they don’t.

2. Step Out Of Your Comfort Zone

It helps to be flexible and step out of your comfort zone because you never know where your match will come from. Be open to attending singles events, potluck mixed meals, new shuls, new restaurants, using a shadchan, putting your profile (and picture) on dating websites, and going on Facebook divorce groups.

It’s important to make as many connections as possible. Just because you didn’t think you were compatible with someone you dated doesn’t mean his or her friend won’t be perfect for you. So be friendly and let your dates see you for the person that you are. After a date gone wrong, it’s important that neither person walk away feeling dejected.

3. How Do I Do My Research?

With the advent of Facebook, it’s so easy to check someone out. I do a search, look at our mutual friends and message the ones that I’m closest to with a request for information. If the person isn’t on Facebook, and I was set up through Saw You At Sinai or a shadchan, I start by calling his references.

I ask those references for names of other people who may know him (or her). It helps if you have a rabbi or friends who have contacts in the neighborhood he is from. It’s important to determine if this person is stable and has healthy relationships with others. Be careful of he said/she said information. Each side in a divorce has a story, and you have to sift through what you hear to make the best judgment possible. There is no fast and easy rule to determine the truth. However, if you’re still confused and not sure what to believe, you can start by feeling someone out over the phone or giving it a date or two to see.

4. Is He Date-able?

If someone has cheated, dealt with an addiction, was abusive, etc., should you automatically stay away? If you’re willing to be open, find out if that person has made strong efforts in therapy towards recovery. Are credible therapists backing him/her? Are there several years of recovery under his or her belt?

Are you taking a risk? Yes, but life is a risk and anyone can fall. You don’t know where anyone will be five years from now. With the proper support services and a strong will, sometimes a person is capable of change.

5. Our Religious Levels Are Different

Everyone has things he or she won’t compromise on religiously. If you’re willing to date someone who is traditional and growing, determine exactly what you can and can’t live without. You need to ask yourself if you can focus on the content of your date’s character instead of questioning his or her religious level. Can you appreciate that person without pushing him or her to grow at your pace? I believe that being mutually understanding and respectful of someone else can be grounds for a healthy relationship.

6. Just Divorced

If you are dating a newly divorced person, be prepared to hear a lot of venting about the ex. You will most probably hear about every issue in the marriage, explicit details about the civil divorce case – and a lot of negativity. Although there are several exceptions, in general I would suggest allowing a person to heal for at least six months to a year after the civil divorce and get are finalized before agreeing to a date. A year is a good amount of time to transition and gain some distance and detachment from an ex-spouse. Hopefully he or she will have used the time to reflect, do some inner work, and process the marriage and divorce.

7. Slow It Down

When a person is used to being in a marital relationship, it can be easy to see a dating partner in the role of a spouse and get comfortable very quickly. It’s easy to get swept up in the excitement of a new relationship and want to be together all the time. When this happens, that excitement can fizzle out sooner than you think – especially with online dating. Many of my friends have experienced the intense two-week contact, and then never hear from the other person again.

It’s really important to pace things out and give a relationship the time and space it needs to build. It’s important not to emotionally unload every issue onto the person you’re dating because the relationship doesn’t have the strength needed to weather any storm. It’s also important to maintain a level of privacy, because you honestly don’t know if you will end up with the person that you’re dating. It goes without saying that any information spoken about during a relationship should be kept private and not repeated all over town after a breakup.

8. Consider Your Kids

Sometimes the people we date have issues with our children. There are little hints they drop while we’re dating that should tip us off, but because we really like the person, we overlook them. One man I dated kept telling me I was forcing him to grow up and he wasn’t sure he was ready to be a stepfather. Look at your date’s reaction when you tell stories about your kids. See how he or she reacts if you have to cancel a date because of a parenting emergency.

Make sure you ask if the person you’re dating wants more children. It may sound like a given but I’ve encountered men who have had their kids and didn’t want any more. It’s also important to find out what your date’s children are like and how the dynamics would work if you combined families.

9. Emotional Stability

Men who don’t have their life in order, a.k.a. are not emotionally stable, may or may not find stability anytime soon. You are blessed if you find that out sooner rather than later.

Some signs of emotional instability: he doesn’t have an apartment or regular place to live, he’s in between jobs, can’t stick to his decisions, makes grandiose statements and changes his desires daily. Some examples: “Let’s move to Europe,” “I think I’ll change careers and be a ___” “I want to blow money on ___.” You get the point. He consistently doesn’t follow through and do what he has promised to do, and talks big. His feelings for you may change rapidly and go from being crazy in love with you to having serious doubts. Remember, this isn’t about you. The person you’re dating needs time to get his life in order. There may always be someone desperate enough to settle for this type of person, but you need to ask yourself, why would you be willing to tolerate this person and stay in the relationship? Introspection is key here.

10. Self-Sabotagers

If someone has a history of childhood abuse or severe dysfunction, chances are, he or she will continue choosing people who perpetuate dysfunction. That is why therapy is important. Sometimes the person he or she dates will share similarities with a dysfunctional parent.

For example, if David had to parent his mother growing up, he may seek out a woman who is incapable of caring for herself. Two men I previously dated, both of whom had experienced childhood trauma, told me that I was the healthiest person they had ever dated. That was a message. When a person is comfortable in a dysfunctional relationship, he will be calm with a healthy person, but eventually sabotage things. Both men eventually self-sabotaged our relationships. People who self-sabotage feel that they don’t deserve to be happy or loved. When someone shows them love or vocalizes it, they cannot deal with the feelings. Counseling can help a person make healthier relationship choices and gain self-worth.

11. Let’s Take a Break

Certain men/women will say they need a dating break because they’re “not ready to be in a relationship or they need time to get their lives in order before continuing to date.” If these statements are true and not just an excuse to end the relationship, these people probably shouldn’t have started dating in the first place. However, many people will jump right back into the dating scene the day after they have requested a break. This means they can handle dating, just not dating you. Requesting a break doesn’t usually lead to anything more than either dating again at a later time with an eventual breakup, or a break with a soon-to-be followed break-up, but it feels more comfortable to just ask for a break.

12. The End

It’s fascinating to observe the way a person treats someone at the end of a relationship. That person could have been the biggest mensch ever during the dating period, but when it’s over, somehow the person ending things shows you a shocking side. When ending the relationship, it’s not necessary to list everything you found wrong in the other person. You can just say that you don’t think things will work out.

What I personally don’t appreciate is closed communication during the dating period. If someone didn’t think things would work out, he should have brought up those issues while we were dating. Choosing to let issues pile up and then breaking up with someone isn’t very constructive because once it’s over, it’s over.

A Few Final Words

Second time around dating can be more than frustrating. It can feel like someone’s repeatedly taking a sledgehammer to your heart. The rejection and emotional investment involved with dating and singles events can be overwhelming.

What I have learned is that I need to give a relationship everything I’ve got because second chances are rare once a relationship ends. I’ve also learned to not tolerate disrespectful behavior. If someone is sporadic or inconsistent in his contact with me, I will bring it up. If nothing changes, I will break things off – out of respect for myself.

Those of us who have been divorced awhile often wonder why it has taken so long. I look back at how I was seven years ago when I first got divorced and see a completely different person in my mirror today. The lessons that I’ve learned about men, relationships and communication, the quality friendships I’ve built, the intimate time I’ve spent with my son, and the growth I’ve gone through are invaluable.

I’ve also learned that you attract who you are, so it’s important to create the life that you want someone to join. I can only hope that we will look back on this time, hopefully soon, and know that it was all worth it.

My fellow dating warriors, may you be blessed with awareness, openness, and perseverance.

Published: April 21, 2014


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Visitor Comments: 11

(6) Anonymous, June 8, 2014 6:19 PM

Wonderful article and objectives!

I just linked your article to a Jewish singles group on Facebook. It made me reevaluate my own desire and ability to date, even after seven years of being divorced.

By the way, I love the fact that in the "About the Author" section, that you "look forward to no longer having the expertise to write dating articles". Since I relate to that statement and also dabble in literary pursuits (including writing dating advice), I found that to be extremely funny.

Alanna, August 15, 2014 5:06 PM

Thank you so much! I really do look forward to that! ;-)

(5) Shellie, May 2, 2014 3:48 PM

Thank you...after a 28 year marriage your penned words help

Learning to be alone is the "it"....hard & painful, albeit a must.

Anonymous, August 15, 2014 5:06 PM

Definitely true

(4) Alanna, May 2, 2014 2:38 PM

I wrote another article awhile back to raise awareness for divorcees. This is the link: http://www.jewishpress.com/sections/family/marriage-relationships/beyond-the-picket-fence/2010/07/28/

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