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How Dating and Sex After Divorce Is Different

Written by Jackie Pilossoph. Posted in dating after divorce, Sex




dating and sex after divorce

One of the biggest fears for divorced men and women is getting back into the dating scene and having sex. If you think about it, a recently divorced person hasn’t been on a first date in years — maybe even decades. Here are four ways dating and sex after divorce is different than before you were married.

1. You no longer look for a mate, you look for a soul mate

As a young person dating, I remember looking for that perfect mate, the one who was going to make a great dad, who would be a good co-provider financially, a person who was looking to embark on the same life journey as I was, and someone who would grow old with me. Now that that plan was shot to hell, what’s plan B?

I find that most divorced people are just looking for someone they like and nothing more. They’ve been so unhappy in their marriage for so long that just spending time with someone who makes them laugh, or who challenges them intellectually, or who makes them feel good about themselves is all they really want. There’s no clock ticking and no pressure to have children, and so there’s no rush to get married.

Many divorced people just enjoy that refreshing feeling of being happy, really connecting with someone, and perhaps, falling madly in love without worrying about how perfect or not perfect the person is for them.

2. You now have other people to consider: your kids

When people are young and single, the only responsibility they have is to get to their jobs every morning — and for even the hardest of workers, that still leaves time for socializing and dating. After a divorce, however, many people have a job and kids, which sometimes feels like there are no more slices in your pie for anything else. You can’t spend hours and hours on a date because you might have a babysitter at home, you can’t talk on the phone every night, and get-togethers are limited.

Also, kids can make or break a post-divorce romantic relationship. If your kids like your new boyfriend (or girlfriend), everything is wonderful. If they don’t, feelings get hurt and things can get complicated.

Click here to read the rest of the article, published in the Sun-Times. You really need to read #3 and you really, really, really need to read #4!


First Date Tips: What You Should Talk About and What Topics are Taboo

Written by Jackie Pilossoph. Posted in dating, dating after divorce


first date tips

First dates aren’t easy, especially blind dates, which is why this post is dedicated to first date tips.

First dates usually consist of moments of awkward silence, fear of having food between your teeth, wondering if he noticed your nervousness, thinking you said something really stupid and wishing you could take it back, and the worst one, trying to think of what the heck you should talk about!

On my recent Steve Harvey show appearance, where I gave divorce advice to two recently divorced women, I was asked to give some first date tips.

One of my tips was: don’t talk about why you got divorced for more than a few minutes. Why? Because your date might be going through his or her own divorce, and is probably viewing dating as refreshing. The last thing he or she wants to do is relive your divorce, hear your complaining and analyze what your ex spouse might or might not be thinking and feeling.

I got to thinking, besides not talking about your divorce, there are other topics of conversation you should stay away from on a first date. There are also some great topics that are perfect for a first date; topics that will spark intellectual, emotional and positive conversation, hopefully resulting in a second date!

1. Bad topic: Politics. Obamacare is not first date stuff! People get really sensitive and offended if the person they are with doesn’t share their political views.

Good topic: What’s in the news. If you aren’t already watching the news and reading the paper, please start. Aside from the fact that it makes you a more intelligent person, that it’s healthy to be informed and knowledgeable, and that you are setting an example for your kids, knowing what’s going on really does make you more attractive and interesting to your date. Plus, it sparks interesting, thoughtful conversation. I know you are busy, but you can get caught up on world news if you invest even 15 minutes a day reading the paper or news online.


2. Bad topic: Old relationships. Just like your date doesn’t want to hear about your ex, no one wants to hear about an old boyfriend you still miss dearly, or the one who got away.

Good topic: Kids or family. Your date went out for dinner with you to get to know YOU, and the best way he or she can do that is to hear you talk about your kids or your family, the people you are closest to. I always like to watch a man’s expression when he talks about his kids. That tells me everything I need to know about what kind of father and person he is. Or, one time I was dating this guy and he talked about how “stupid” his mother was. I RAN the other way, seriously.


3. Bad topic: Your job (if you are unhappy). I think there are two types of people. Those who go to their jobs only to bring home a paycheck, and those who truly have passion for what they do. If you are the former, keep your job description brief and instead talk about your hobbies and/or interests outside of the office. By the way, I have nothing against people who work for a paycheck. I’m not judging. I’m just saying, whatever you talk about with your date, talk about it with passion and happiness, versus “My boss is an asshole.”

Good topic: hobbies, interests, travel. Let’s say you just got back from Spain, or you have a trip planned to China. Or, you just started doing yoga and you love it! (That’s what I would talk about if I had a first date tonight.) Or, you are learning Spanish. First dates are all about figuring out if you want to have a relationship with this person. And so much of that comes down to having things in common. So, tell your date what turns you on!


4. Bad topic: Sex. It’s just in bad taste to start talking about sex on a first date. It just is.

Good topic: Love. You might disagree with me, but I think it’s okay to talk about love and relationships, and what you think makes a good one. Get it on the table! Tell your date what you want and don’t want. I’m not saying to tell your date you want to be married within the year, but saying, “I’m really looking to fall in love,” or “I would like to be married again someday” aren’t forbidden. Use your best judgment, but be honest. Chances are, your date wants that too.

In closing, of all the first date tips I can give, the best one is to just be yourself. Be authentic. BUT, be YOUR BEST self. Offer your date the things you love about yourself. Your passion, your heart, your humor, perhaps. Leave your divorce baggage at home tonight!



Divorced Girl Smiling is Listening! Divorce Advice in Response to Your Comments

Written by Jackie Pilossoph. Posted in cheating and divorce, divorce advice

Divorce Advice





Divorced Girl Smiling has been in existence for 14 months, and during that time, I’ve done my best to offer divorce advice not only in an inspirational way, but I constantly strive to be impartial, nonjudgmental, and of course, funny, at times to lighten things up.

What I want you all to know is that I’m listening! That means when you send in your comments, I read them. I hear you. I try to respond to some of them, but time constraints and work sometimes prevents that.

Well, now I am responding! Here are three comments you made, along with my answers.

Divorcing with no children

I am in my late 40′s, married almost 22 years, and no children. It see so few conversations that deal with women who are in a similar position. If people feel alone and have children at home, imagine the loneliness of realizing you are completely alone in this situation. It seems like none of the blogs address this. I really feel like an outlier. Is that so?

 What you seem to be asking is, “Is divorce less of a big deal if you don’t have kids?” Here’s my answer: NO!

I apologize if I give that impression in my posts. I think because I have children, I write what I know. What I can tell you is that I can’t imagine your breakup being easy after 22 years together. I am so very sorry.

However, I would like to address your comment about loneliness. People who have kids have that same loneliness you have, even when the kids are around. Not because we don’t love or appreciate our children, but because every divorced person feels that void of having a spouse, a partner, a friend with them, and it’s a void children can’t fill. You can also be married, and if it’s to the wrong person you probably feel loneliness.

My wife gave up too soon

 I just had to add something to this as a man who’s wife just left him 4 weeks ago and asked for a divorce. I have given my heart, soul, mind, and body to my wife. It hurts more than anything I have ever dealt with. I am in the armed forces and had to deal with a lot that would make people cringe. So hear me when I say that just leaving and saying I want a divorce is the wrong way to end a marriage. Go to counseling together and talk about your issues, date each other again, make sure you both do everything humanly possible, especially when there are children involved. Now there are good reasons to end a marriage but what I am talking about is for those men and women who don’t have no reason other than, I don’t love him/her anymore, or they do this or that and I just can’t take it anymore.

 I’m mad at her for abandoning me and the kids, our family that we spent ten years putting together.  If a divorce is in your horizons, do everything you can to save it no matter how you feel, but if you put everything you have into it with your spouse, and if it still is not working then yes talk about divorce. You will find yourself more at peace, and it will be a much smoother/amicable transition.

 First of all, the tone of this apparently shows what a rational person you are, and I applaud you for that. This doesn’t sound like so many angry, bitter, irrational messages I receive. This is smart and thoughtful. Not to mention, you are in the armed forces so I want to give you a big hug and say thank you for what you provide everyone in our country every day!!

I am so sorry your wife left you. I truly am. It is very painful, I’m sure. Are you telling me your wife wouldn’t even consider counseling? That’s so sad to me. You are correct when saying “date each other again.” Marriage is a constant effort, and I don’t mean that in a bad way. But when people forget to water their plants, they die. Same goes for marriage.

I am wishing you all the best and I have faith that at some point, you will realize that things happen for a reason and you will end up very happy. Just keep being a great dad and do things for yourself, as well!

Child support money NOT used for our children

I pay $2000/month to support 2 teenage children. My ex-wife has never really signed them up (or allowed them to be signed up for music lessons, SAT prep classes, art classes, or any one the myriad things most functional parents do.) Yet she works in a profession that earns her a high 6-figure income. She rarely seems to purchase clothing. She has saved less than half of the amount that it would take to send them to a state university.

 It doesn’t take a particularly savvy accountant to sort out the fact the check I’m sending her is not going to support these kids. I love my children dearly and don’t resent in the least what I do for them; but the money I send to their mother – I will resent in perpetuity, because it is plainly observable that it is disproportionate to their actual and realized needs.

 Okay, so this is a tough one for me, being on the other end, i.e. receiving child support. I feel like what you are feeling is very common, and I’m sure you must be frustrated beyond belief. Here’s what I can tell you as a single mother. With two growing kids who are eating me out of house and home, a mortgage, bills, even school expenses, I think there are a lot of things I spend money on for my kids that my ex really doesn’t realize, only because he isn’t here to see the checks I’m writing. Again, I can only speak for my situation, but my child support check isn’t paying even half of my kid expenses.Even with MY income, I struggle financially.  And I don’t resent my ex for it, I’m just saying, that check doesn’t go as far as you think.

My advice to you is to ask your ex, talk to her. I know that’s difficult but if you go about it in a nice way, and just say, “Could we maybe talk about why you aren’t signing up the kids for these classes? Or buying them new clothes?” Let’s be honest, she’ll probably get really defensive, so be prepared. But isn’t communicating worth a try?

If you have any questions or comments that you’d like me to address with some divorce advice, please reach out!  



Divorce and Children: How to Answer Those Tough Questions They Ask

Written by Jackie Pilossoph. Posted in Children and divorce, Divorce and children


Divorce and children








When it comes to divorce and children, there is nothing more gut-wrenchingly sad than when your child, wide-eyed and hopeful, asks you this question: “Are you and dad ever going to get back together?”

These and other divorce questions from kids can feel like a punch in the stomach, causing anxiety, guilt and sorrow. There are no magical answers to your kids’ questions because a divorce is undoubtedly very difficult for any child. But the silver lining is, if you put some thought into how you answer these difficult questions, if you have an unselfish attitude by filtering your answers, and if you end every answer with “We both love you,” it makes the sting a lot more manageable.

Here are six common questions kids ask after a divorce, and suggestions on how to answer them.

1. Why did you and mom/dad get divorced?

Because your dad was cheating on me. Because your mom drinks too much. Because dad and I can’t stand each other and we don’t want to live together anymore. This is what you are probably feeling and what you’d like to scream at the top of your lungs. The fact is, you can’t. A better way to answer this very difficult question is by saying something like this: “Your dad/mom and I once loved each other very much, but people change and people grow apart. Neither of us wanted that to happen, but it did. We tried very hard to work things out, but in the end, we both felt it was better. What hasn’t changed is that your dad and I still love you, and both of us will always be here for you.”

2. Do you still love mommy/daddy?

You might and you might not. If you do still love your ex, you might want to say, “There is a part of me that will always love your mom/dad. We share so much history, and most importantly, we share you. I will always love him/her for giving me you.” If you don’t feel like you can honestly say something like that, you could answer, “I don’t love your mom/dad in the same way I used to. I respect him/her and I think he/she is a good mother/father. But now we are just going to be partners in parenting and hopefully good friends, some day.”


Click here to read the rest of the article! Wait till you read question #5!





Selling your Home During Divorce? 5 Tips to Make it Easier, Quicker & to Get More Cash

Written by Jackie Pilossoph. Posted in divorce process, relationship with ex


selling your home during divorce








Meet Stephanie Hofman, who I am calling “The Divorce Realtor.” Stephanie has a niche in her business, working with divorced couples. If you’re selling your home during divorce, Stephanie is who you want to call! 

When I asked Hofman, (who is happily married, by the way) why she chose to specialize in divorce, she told me that early on in her real estate career, she worked with a divorced couple.

“I found that I had a knack for being able to play the delicate and impartial role necessary between the two parties,” she said. “It’s gratifying to help people through such a trying  time and know that I’ve made something easier for them when so much is complicated.  I also realized that there aren’t enough real estate agents who are making it a priority to address the specific needs of this segment of home sellers.”

I asked Hofman to offer some tips to make selling your home during divorce easier, quicker, and of course, an experience where you get the most cash. 

Do’s and Don’ts of Selling During Divorce by Stephanie Hofman

There are few situations in life more complex or emotional than getting a divorce - throw in selling your home during that time, and you’re adding a thick layer of stress to the situation. Keep these “dos and don’ts” in mind – they can help make the process go more smoothly.

DO hire a professional Realtor – DON’T sell by owner. Selling by owner is tough in an ideal time – there are disclosures to complete, processes and laws to be aware of, plus huge decisions to be agreed upon – but doing it while navigating the waters of divorce  can add a myriad things to disagree about. You’re much better off hiring  qualified real estate broker who can be a neutral party and guide you through the transaction. Choose someone without close, personal ties to either individual; someone who will communicate equally with both soon-to-be exes – as well as with attorneys/mediators – and facilitate collaborative decision making. Don’t undertake this complex and important task without professional guidance.

DO treat it as the business transaction that it is – DON’T let your emotions take over. Selling your home is, at it’s core, a business decision – ideally, you want to get the most for your home in the shortest amount of time.  Your home’s value is not determined by your emotional ties to the home but by the current marketplace. During divorce, especially one that’s contentious, emotions are heightened and decision making can be affected by anger and sadness. Don’t let your emotions get the best of you and you’ll be able to make the best decisions possible.

 DO have a pricing plan – DON’T try to figure it out along the way! Your Realtor will provide you with comps and advise on the best list price for the home. Once you have decided – or compromised – on this, work with your agent and attorney/mediator to have a schedule in place for price reductions, should they become necessary. For example, if you are pricing your home at $600,000, determine when you will have a price adjustment, say, every 30 days, and of what amount – perhaps 5% of the price. Name what a reasonable offer would be to accept, such as an offer that comes in, or is negotiated to, within 5% of asking. These are things that even the most happily married sellers don’t always agree on, and it only grows more difficult if there’s animosity between the the sellers.  A firm pricing plan will clarify steps and eliminate the need for costly court visits and additional discussions with attorneys/mediators. Don’t start the process without making sure both parties have the same expectations with regard to pricing – knowing in advance what moves to make will keep the process running as smoothly as possible.

DO stage a happy home – DON’T leave clues that there’s a divorce pending. When half of the furniture is gone or the master bedroom closet is half empty and only contains women’s clothing, the red flags go up in buyers’ brains. They will infer that the sellers are “desperate” and will be tempted to low-ball. You may consider professional staging to fill in the places where furniture is missing and ask a friend to store his off-season clothing in the closet to make it look full.  Also, have a plan in place for showings. The home must be accessible to buyers – they won’t buy what they can’t see! – so ensure that you and your soon-to-be-ex both understand this and, if necessary, put a “showing plan” in writing. Don’t give buyers the wrong impression about your willingness or level of motivation to sell.

 DO understand what selling your home will cost you – DON’T be surprised at the closing table! There are a variety of costs associated with selling your home – including paying of the mortgage of course, but also transfer tax fees, attorneys fees, title insurance, property taxes, and commission to your brokerage.  Ask your agent to prepare a list of closing costs so you will know exactly what your proceeds will be and can determine if and how they will be split. Good news: if the divorcing couple retains co-ownership, each are eligible to claim up to $250,000 in tax-free profits from the sale, even in one of the spouses isn’t residing in the home, as long as the residing spouse meets the 2 of 5 year occupancy test when the home is sold.

Thanks Stephanie! 

Stephanie Hofman is real estate broker with Coldwell Banker in Highland Park who acts as her clients’ guide, advocate and educator throughout the entire home buying/selling process. Stephanie specializes in helping homeowners sell their homes during the difficult transition of divorce. Find out more at or call: (847) 652-1902.


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