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Remarrying Your Ex: Can It Work?

Written by Jackie Pilossoph. Posted in relationship with ex, Second marriage

remarrying your ex






Someone on Cyber Dust sent me a question: I have been divorced for several years. Is it normal for divorced couples to try it for a second time? In other words, can remarrying your ex actually work?

The best way for me to answer this question is to tell you two stories of divorced couples I know who got back together.

The first couple was married for several years. They divorced and then got back together and got remarried. They are now in the process of getting divorced again. To me, this is very sad, because hearing a divorced couple is remarrying is inspirational. It’s a happy ending and sort of signifies true love, doesn’t it? A second divorce is just depressing. I don’t know the details of what caused the first divorce or the second, but I have to believe it was the same issue. The good that came out of it is, at least they know for sure that being together isn’t right, and they don’t have to spend the rest of their lives wondering ‘what if.’

The second couple I know has a hopeful story with an uncertain ending. They divorced several years ago and after about 5 years after the divorce started dating again. They have been together again for about 5 years and seem to be doing really, really great. I recently asked the woman if she thinks they will get remarried. Her answer was, “Maybe. I’m not sure. We’re just really happy.” Now, maybe she just doesn’t want to tell me, and maybe they will have a surprise wedding. Or, maybe they are happier as a couple dating than they were husband and wife. Does it really matter? They are together. That’s what really means something.

The issue I have with divorced couples reconciling is the same issue I have with on-again off-again relationships: what’s to stop the same old issues from creeping back up again? In other words, what is going to be different this time? If nothing changes, the couple will ultimately end up divorced again. Also, people and relationships tend to stick to the same old patterns, so what happened in the past will most likely happen again in the future. UNLESS—they make changes to break the pattern.

If a divorced couple is thinking of getting remarried, I think they really need to address the issue or issues that led to the divorce and deal with it. Therapy might be a good idea. Or, lots of really honest, heart to heart conversations that aren’t sugar coated.

The other thing is, as time passes, people tend to remember all the good stuff in a relationship and forget the bad. It’s just human nature. The mind recalls beautiful memories, and blocks out what’s too painful.

There are a few scenarios in which a divorced couple might have a very successful second marriage together:


  1. Maybe a couple got divorced because one of them had an addiction that is now under control. The absence of an addiction makes a huge difference in a marriage.


2. Timing is everything. Maybe there was immaturity, dreams that had to be fulfilled, other people involved that caused the marriage to fail. Maybe better timing could make the difference.


  1. If both people are willing to own up to their mistakes, recognize their faults and apologize to each other—not just because they want to get back together but because they really mean it—I think the second marriage to each other has a decent chance of working.


Here’s the thing. I’m sure there are people reading this who are cringing. Most divorced people actually have no interest in getting back together with their spouse because they have resentment that runs way too deep, or one of them is remarried or involved with someone else.


But, the bottom line is, if you loved someone enough to marry them, the divorce was probably heartbreaking, and I don’t care what people say, I think if love was once there it can return (except for inexcusable behavior such as physical abuse). So, what’s wrong with taking a second chance on someone you loved enough to commit to the first time? True love is a pretty powerful thing and everyone makes mistakes. Remarrying your ex really makes “Till death do us part” ring true (no pun intended.)


Are Sweatpants a Cause of Divorce? Indirectly, yes.

Written by Jackie Pilossoph. Posted in Marriage advice, relationship advice


cause of divorce





cause of divorce



What’s the cause of divorce? There are several. In my Love Essentially column, published yesterday in Chicago Tribune Pioneer Press I address sweatpants as an indirect cause. 

Do You Sweatpants Really Cause Divorce? by Jackie Pilossoph

I have always been a huge fan of actress, Eva Mendes. I loved her adorable performances in Stuck on You (2003) and Hitch (2005) and I even thought she was great when she played the malicious girlfriend in The Women (2008).

So when I saw the clip from her infamous interview warning, “Ladies, the number one cause of divorce in America — sweatpants,” I laughed.

What was utterly shocking to me was the aftermath of the comment: the backlash she received from those offended by her disapproval of sweatpants! Not only did Mendes feel the need to apologize on twitter for her sweatpants remark, but her boyfriend, Ryan Gosling even had to comment on her behalf, stating on twitter, “Obviously the sweatpants remark was a joke. Wearing them now.”

My question is, why is everyone so sensitive and defensive when it comes to sweatpants? Clearly, they are an item of clothing meant for comfort and not for the purpose of looking sexy or attractive. In other words, they are what they are. Why the eggshells?

Do I agree with Eva that sweatpants cause divorce? Yes and no. I will be the first one to admit that I adore sweatpants, and spend a lot of time in them. Just ask anyone in my neighborhood if they have seen me at our local Starbucks in the morning wearing, ahem, sweatpants. They’ll vouch for me. And, I do not believe sweatpants were the cause of my divorce.

All that said, I believe there is a time and place for sweatpants in a marriage (or a serious relationship). Lounging around in sweatpants with your spouse and ordering a pizza on a lazy Sunday can be blissful. However, what I believe to be the real issue of sweatpants lies in the frequency. In other words, maybe Mendes should have said, “Ladies, the number one cause of divorce in America-wearing sweatpants more often than not.”

In my opinion, there are many men and women in relationships who get a little too complacent in their daily appearance, and perhaps because of busy schedules end up putting how they dress at the bottom of their list of priorities. I know I have been guilty of it at times. But repetitive days of no makeup, an old t-shirt, unwashed hair and yes, sweatpants, can lead to a lack of romance, sex, dates and possibly a romantic disconnect which can cause marital problems and divorce.

I happened to be out at a nice restaurant in my neighborhood a couple weeks ago…Click here to read the rest of the article, published yesterday in Chicago Tribune Pioneer Press.


7 Tips for Those Thinking of Divorce

Written by Jackie Pilossoph. Posted in Thinking of separating


thinking of divorce

Jennifer Dillon Kotz, Partner, Schiller DuCanto & Fleck








No one wakes up one day and says, “I want a divorce.” Thinking of divorce is usually something that has been going on for months, even years.


Thinking of divorce involves weighing countless pros and cons, trying to imagine your future both ways, considering children, and really tapping into your gut and your heart.


Even if someone decides to pursue a divorce, that person might go back and forth 10 times before actually bringing it up to their spouse. And then, the spouse might convince them to try again. The couple might go back and forth for months or years before they decide to work things out or split for good. I’ve seen couples go in both directions so there is no right or wrong answers.


All that said, if you are thinking about divorce, there are certain steps you might want to take to prepare. They might seem dishonest and sneaky, but, I don’t see it that way at all. Preparing is smart, practical, and could save you a lot of time and money in the future. Preparing also helps you weigh everything involved in a divorce, which then helps you in your decision of whether or not to divorce.


Jennifer Dillon Kotz is a divorce attorney and partner at Schiller DuCanto & Fleck. I recently had a conversation with Kotz, who has been with the firm for 17 years, and asked her advice on what specific steps people thinking about divorce might want to take. Here is what she offered:

7 tips for people thinking about divorce:


  1. Make copies of federal and state income tax returns from the past five years. Those documents will show income, which is much needed info for your attorney.
  2. If you don’t have a credit card in your name, open one up in case of an emergency.
  3. Establish online access to your joint bank accounts and check the account regularly for any unusual activity, which could include excessive spending or withdrawals
  4. If you have a safety deposit box, photograph and inventory the contents.
  5. Obtain a copy of your credit report to see if you have any liabilities (including unpaid medical bills) you might be unaware of.
  6. Obtain a copy of your will and powers of attorney. Again this something that will help your divorce attorney and will need to be changed.
  7. Go for a consultation with a divorce attorney even if you are still unsure if you want a divorce. Knowledge is power and to be educated will help you weigh the pros and cons and influence your decision.

These are all smart, but I can’t resist adding a few tips of my own:


  1. Keep a private journal. I believe that when you write things down it helps make things more clear. If you look back and read what you wrote, it helps solidify your decision. The memory has a way of blocking out red flags, but it’s hard to ignore it in print.
  2. Talk to a therapist. An unbiased professional who doesn’t know you isn’t going to say, “You need to leave him, he’s an *sshole,” like your girlfriend will. The therapist will be objective and help you draw your own conclusions.
  3. Try to imagine your future. Then ask yourself if you think you and your partner could make changes to get to a good one. In other words, is it fixable? Trying to reignite a spark is more doable than trying to get someone to break an addiction he or she doesn’t think they have.
  4. Forget fear. Getting divorced is scary and so is staying in a marriage that isn’t working. So, don’t make decisions based on fear. In other words, don’t stay or go because of fear. Do either one based on what YOU think is the better choice. Either one will be scary.


Jennifer Dillon Kotz is a partner at Schiller DuCanto & Fleck LLP who has been litigating family law cases for 17 years. Also certified in collaborative law, Kotz has received recognition in the Chicago Daily Law Bulletin, Illinois Super Lawyers Magazine, and Crain’s Chicago Business. Kotz is a graduate of Loyola University School of Law and has lectured on family law topics for the IICLE, the Chicago Bar Association, and the DePaul Law Society. Learn more:


Advice for “My Ex and My Best Friend Are Dating!”

Written by Jackie Pilossoph. Posted in relationship with ex


my ex and my best friend are dating






Advice for a woman who wrote to tell me, “My ex and my best friend are dating:”

As I just passed the one-year anniversary of my divorce, I’ve learned that
what many had suggested at the time of my separation is most likely true:
there is “something” between my ex and my former BFF. I have come to
accept my divorce but I am struggling with accepting her betrayal. The
signs were there that there was at least an emotional connection between
them, but I denied it, telling everyone “she would never do anything
like that.”

She began to end her marriage when my husband moved out. She had dumped me
by this point. At the one year mark, she kicked her husband out. I
supported their marriage, encouraging Retrouvaille (a Catholic weekend
program for troubled marriages) and by encouraging her husband to move back
in and fight for his marriage. I fasted and prayed for them, another
Catholic tradition. Despite my efforts (as if I could save their
marriage), they divorced.

Now, it appears she is involved with him. I don’t want this back-stabbing
witch around my children. I think the kids feel the same way. My teenage
told me that my daughter was scolded by her father for not speaking to
my former BFF. When I asked my son how he feels about it, he said that
when his dad tells him that there is a relationship, he will walk out of
his house for good. Their reactions make me feel good, like they are not
accepting what she has done.

In the meantime, how can I get past this? It’s so clichéd: the best friend
ends up with the former husband. It is hurtful and frustrating. Any

I can’t even begin to tell you how badly I feel about your situation. It is so very difficult, and honestly, what your friend did to you is absolutely disgusting. I’m so sorry you have to deal with this.

I noticed that you said, “I’ve come to accept my divorce but I am struggling to accept her betrayal.” I disagree that you accept your divorce. It’s only been a year and I don’t believe that anyone is healed and completely accepting after a year. I think it takes many years to fully accept and heal. That’s OK, by the way.

Now, onto your former friend. It sounds to me like subconsciously you knew there was something going on with her and your ex for a long, long time. Otherwise, you wouldn’t have tried so hard to save her marriage. I’m not saying you aren’t a good person or a good friend, but you knew. Deep in your core, you knew. But, you protected yourself because you couldn’t bear the thought. And then you tried to fix her marriage so that it wouldn’t happen. It’s understandable and I’m sure anyone would have done the same thing.

But onto what is happening now. They are together. She dumped you because she chose him over you. That is immensely hurtful, devastating and frustrating, but if you think about it, what have you really lost? NOTHING. The bottom line: she was not your friend.

When it comes to girlfriends, I feel pretty strongly about the importance of having truly loyal friends who are there for you when you need them most: the ones who are giving and selfless and really come through in a time of need. This girl shows really unethical and bad character. I’m sorry. I would never do that to my best friend. I don’t care how attracted I was to her husband, I would realize that he isn’t the only man on earth and I would move the hell on.

Let’s talk about the future. What if they stay together and get married? I would say, (and I know this is really really hard to hear) but you’re going to have to learn to live with it and be civil to her. Do it for your kids. Because don’t you want them to have a relationship with their dad no matter what? Just think about it. I know it will hurt like hell to be nice, but you can do it.

But let’s be more realistic. Think it will really work out? I don’t. Sounds like she left her husband for him, and I never have faith in relationships that begin with cheating and lies. Their relationship right now is sexy because it’s hidden. It’s a secret. But deep in their minds, it’s shameful and they both know it.

Something similar happened to me when I was first separated. The girl wasn’t as good of a friend as yours sounds, but it seriously drove me insane when I found out they were dating. I could barely function at times. I think the relationship lasted 6 months and I later realized what a waste it was making myself nuts over it. That said, I still cringe when I see the girl! Lol.

My advice to you is, try not to focus on THEM, but instead on YOU and your kids. There are a million men out there and you will fall in love again someday and then they won’t really matter, whether they are together or not.

Lastly, I would tell your son that even if they announce they are a couple, he shouldn’t shut out his own father. Trust me on this. Your kids still need him.



Ever Been In An On-Again Off-Again Relationship?

Written by Jackie Pilossoph. Posted in breakup advice, dating, relationship advice


on-again off-again relationship






on-again off-again relationship



Ever been in an on-again off-again relationship? I find them to be very perplexing, and wanted to know more, so I recruited the advice of a relationship therapist and found out, and then wrote about it in this week’s Love Essentially, published today in Chicago Tribune Pioneer Press.

We are Never, Ever, Ever Getting Back Together. Like Ever.                                

 by Jackie Pilossoph

Taylor Swift said it best in her 2012 hit song, “We Are Never Ever Getting Back Together.”

“This is exhausting,” is a line of the lyrics in the song about an on-again off-again couple riding an emotional roller coaster of temporary highs that continually come barreling down every other week like the Goliath at Great America.
Several years ago, I had a friend who was in an on-again off-again relationship, and every time I’d run into him, my first question would be, “Pam or no Pam?” which meant, “Is Pam currently your girlfriend or are the two of you broken up? Again.” This went on for several years, and eventually my friend and Pam broke up for good. If I’m not mistaken, I think Pam is happily married to someone else now.

What I want to know is, why do some couples fall into this pattern? In other words, what keeps them coming back? Stupidity or true love?

For help on the subject, I turned to Anita Chlipala, a licensed marriage and family therapist and the founder of her Chicago-based practice, Relationship Reality 312.

She said the root of couples breaking up usually stems from one or both of the people being dissatisfied in some way, with countless possible reasons. They also might break up because one or both wants to date other people, perhaps to see if there is someone better out there for them.

But what if time goes by after the breakup, and one day one of them picks up the phone and basically says, “I’m not done?” Then what?

“Reasons people might get back together include lingering feelings, fear that they won’t find someone else, loneliness, and feelings of missing the companionship and familiarity,” said Chlipala, who has been a relationship therapist for nine years. “They could also go on several bad dates and start thinking their ex is the one.”

Chlipala said that before couples get back together, she encourages them to answer the question: What would be different this time around? Otherwise, they won’t be able to break that pattern.

Click here to read the rest of the article, published today in Chicago Tribune Pioneer Press.



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