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Beware of Bad Dating Behavior

Written by Jackie Pilossoph. Posted in Uncategorized

bad dating behavior






I want to share something that recently happened to me in an effort to make a few really good points about bad dating behavior and why you should steer clear from someone exhibiting it.

I recently met someone in a business setting, who subsequently called and asked me out. We set up a night and time to have dinner. So far, so good. A day before the date, he texts me and says something like, “hope we’re still on for tomorrow.” I text back, “Sure, looking forward to it.” We set a time and restaurant.

The next day comes along. It gets to be around 2pm and I haven’t heard from him. The date was set for 7pm. I texted him and said, “Just making sure we’re still on. Want to meet there? Should I make a reservation?” At this point, I’m a little annoyed because being the old fashioned girl I am, it might have been nice for him to make a reservation and offer to pick me up. Is that too much to ask? Am I being high-maintenance? Maybe, but I don’t think so.

Here’s where the bad behavior begins. I get a text back that says he has to cancel because a close friend had a family emergency. I’m not heartless or so self-centered that I don’t understand, but here’s where I have a big issue.

Was he going to text me and tell me this? In other words, I texted first. Was he not going to text at all? Was I going to be stood up? Or, was he going to text me at 5pm? Or even 4pm? Or 7pm? My point is, I am a single mother working full time who like most people have limited free time. Did it ever occur to him that if he cancelled, I might want to make other plans? Maybe call a girlfriend for dinner or go to a movie? This is a kid free night for me. Any single parent can understand how you might want to take advantage of that, right?

What I learned from this bad dating behavior is that this person had no regard or respect for my time. But let’s even give him the benefit of the doubt and say that he coincidentally just found out about his friend’s emergency 10 minutes before he got my text, and hadn’t had time yet to contact me. Shouldn’t he have picked up the phone and called me so that I could hear the tone in his voice? So that he seemed sincere? If the situation was reversed, I’d have called him and said the following:


“I am so so sorry that I have to cancel. I feel terrible about it and I really do want to go out with you. Can we make a date right now? How is next Tuesday?”

The reason I would do that is because I would want the person to know that I was sincere, and that he shouldn’t take it personally.

But let’s say the whole thing was a lie–that there was no emergency (although i don’t think that is the case. I will never know.) But let’s just say he changed his mind and didn’t want to go out with me. If it was me, I’d either go on the date and keep it friendly, or I would cancel and just be really honest. Maybe say, “Just feeling like I have too much baggage right now and don’t feel up to it.” However bad it is, the person would probably be livid, but would respect the other for being truthful.

To top things off, he then texts me a couple days later and says, “Just wondering what you are up to today. Want to get together?”

I politely declined, as I no longer have any interest in getting together with this person.

Here’s the thing. In many ways, dating at my age is much much different than it was before I was married, one being that I am going to recognize red flags very very early on. Does that mean I won’t give someone a second chance? Maybe, maybe not. It all depends on my gut feeling.

I just know I’m not settling for bad dating behavior this time around, like I occasionally did, looking back to my twenties, thirties and even in my early forties. It’s not good for self-esteem and for anyone who seeks a healthy relationship.It’s better to be alone than to feel like that.

In closing, I just want to say that I don’t think this guy is a bad person. Actually, I bet he is nice person. But, for me, he’s the wrong person. Why? Because bad dating behavior can only lead to more bad dating behavior, and it just makes you feel bad about yourself for settling for it. In other words, the relationship is already tainted. Not a good way to start off with someone.

Dating that is stressful or disappointing, or that makes you feel rejected or disrespected isn’t good. Dating is supposed to be fun. It’s meant to make you happy. So, seek out good dating behavior instead. And great dating behavior—well, that just makes you feel like you can fly.


Dating Advice: How You Know She Really Digs You

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


dating advice


fighting about money




In my Love Essentially column for this week, published today in Chicago Tribune Pioneer Press, I decided to answer three reader questions: 1. From a guy seeking dating advice, who wants to how you can tell if a woman really likes you, 2. From someone asking how to affair-proof a relationship, and 3.  A guy who wants to know how to tell his spouse that her recent weight gain is unattractive. 

16 Signs She Digs You by Jackie Pilossoph

Jackie, how do you know if she really likes you?

This question warmed my heart and I am excited to help this guy get into the mindset of a woman by sharing just what the heck we are thinking!

So, here are 16 signs that she digs you:

1. Texts and phone calls are answered promptly.

2. She wears lipstick on your dates.

3. She asks you about YOU, seems genuinely interested and seems to care. “How is work?” “Tell me about your family.” “I want to hear a story about your past.”
4. She is interested in meeting your friends.

5. She smiles a lot around you.

6. She puts her phone away at dinner (unless she has young kids who might be calling her).

7. Saturday nights always work for her to get together.

8. She buys you a thoughtful gift, maybe a book she wants you to read or a plant for your house.

9. She offers to cook you dinner from time to time.

10. She talks about a future together. “Maybe we could go to Lake Geneva this summer.” “My cousin’s wedding is in June, I hope you’ll go with me.”

11. She rarely mentions her ex.

12. You’re walking down the street and she holds your hand.

13. She seems vulnerable, but confident, too.

14. She laughs at your jokes, even if they aren’t that funny.

15. If you have to go to the doctor, she offers to go with you.

16. The biggest sign: her kiss. It shouts, “I really like you.”


Is there any way to affair-proof a relationship?
I hear so many stories from men and women who explain that they were utterly shocked when finding out their spouse was having an affair. While I completely understand how that scenario could happen, I often wonder if the cheat-ee turned a blind eye, not letting himself (or herself) see the cheating because it was just too painful, or they were too afraid to confront it.

There are a few things couples can do to minimize the chance that their spouse will stray. First and foremost, communication is a huge component to a cheating-free marriage. Couples should be best friends, and we all know that best friends talk a lot. They open up, they share their inner most thoughts and feelings.

This way, if something is wrong, the other person can address it and the two can try to work things out before one goes looking somewhere else for comfort and/or happiness. Couples also need to nurture the romantic aspect of their relationship by going on kid-free dates and vacations together. A marriage is like a plant or a pet or even a child—it needs to be taken care of, with lots of attention. If it isn’t fed or cared for, it will die.

How do I tell my spouse that she has gotten extremely overweight and it is a turnoff?

This is a tough one. First of all, you don’t have to tell her she is overweight. She knows. Trust me. The question becomes, does she care? Click here to read the rest of my column, published today in Chicago Tribune Pioneer Press!



New NBC Reality Show: “Co-Parenting 101″ Aims to Help Divorced Parents

Written by Jackie Pilossoph. Posted in co-parenting advice








Don’t you feel like there’s a reality show for everything these days? Reality dating and divorce shows seem to be the new craze right now, which is of particular interest to me (obviously.) This includes “Co-Parenting 101” a new NBC reality show in production.


I recently had the pleasure of auditioning with one of the casting directors for the show, who asked me what tips I had to offer divorced parents about co-parenting.


Before I give 8 tips I shared, let me explain what effective co-parenting means to me:


  1. Working together to help your kids through rough times and assist them in solving their problems. Examples: bad grades, peer pressure.
  2. Being on the same page to raise your kids with good values and shape them into productive, loving, caring, happy adults.
  3. Together, helping them make decisions so they can achieve their goals and fulfill their dreams.


When kids see both their parents on the same page, it makes them realize a couple things:


  1. This is the correct way of doing things. – in other words, not just my mom feels this way, but so does my dad, so it must be right.
  2. I’m not going to get away with crap because both my parents are against me doing this. In other words, I can’t go ask dad because my mom said no.
  3. My parents love me enough to talk to each other, even after their divorce. That makes me special and loved.

So, with that said, here are 8 tips for more effective co-parenting:


  1. Communicate. When people get divorced, the last thing they want to do is talk to their ex. Think about it. They just spent many miserable months or years together, followed by a non-pleasant divorce. Since divorce and the hostility in the aftermath almost always stems from some kind of resentment, having conversations with the person who hurt you and/or broke your heart isn’t exactly an attractive idea. All that said, if you stop talking, your kids are the ones who suffer. So, it’s a complicated dynamic. It isn’t necessary to constantly communicate, or to talk on the phone for hours, but for those of you who are stubborn and are saying things like, “I will never, ever speak to him again as long as I live,” think again. Because you really are doing a disservice to your kids.


  1. Don’t play the blame game. Example: let’s say you are deciding what to do about your child’s bad grades. Is it necessary to say something to your ex like, “Well, when he’s at your house, he doesn’t get enough sleep, so I think that’s the reason his grades have dropped.” It’s Ok to think it, but saying it will hinder your co-parenting efforts, which is bad for your kids.


  1. Leave the past in the past. It is very important when communicating to co-parent to avoid bringing up things from the past that have nothing to do with the benefit of your kids. For example, conversations between divorced people can always lead to harsh statements like, “Well, maybe if you didn’t cheat, we’d still be married and we wouldn’t be having this conversation.” Is that helping your kids? No.


  1. Forget societal norms. It’s really sad, but society makes us believe that if you are kind and you get along with your ex, that is strange. It might even be off-putting to the new people that the divorced couple are dating or married to. Don’t stoop to that level. Being friendly and kind to your ex is good. People might say, “After what she did to you, how can you be that nice to her?” The best answer: “Because it is good for my kids.”


  1. Consider going to a therapist together. I know, you just got out of failed marriage therapy for years. Now I’m telling you to go back? You might be thinking, “Forget it!” But a therapist can help teach a couple how to talk to each other in divorce, making co-parenting easier and more effective, and keeping kids happier and well adjusted.


  1. Remember that there are boundaries. Good co-parenting and getting along like two old friends doesn’t mean there is hope you are getting back together. It might be hard for some couples to be friendly, because maybe one of them will interpret it as wanting to get back together. Or, maybe if there are still feelings there, it’s just too sad. Try to remember that co-parenting is all about the kids and what is best for them. It might be hard, but you are doing it for them.


  1. Try to put yourself into your kids’ shoes. My parents are still married, so it’s sometimes hard for me to know how my kids are feeling. But if you try to think, “How would I feel if I was a 12 year old, and if my mom wouldn’t let my dad come into her house?” it might cause you to let your ex come in. It might help you make the right decision. Not saying it’s easy, by the way.


  1. Co-parenting is really about being selfless. The bottom line about co-parenting is, it’s about putting the best interest of your kids ahead of your feelings and your ego. Grit your teeth, suck it up, deal with it. Your kids didn’t ask to be born into parents who ended up apart. So, if you love them, put them ahead of your hurt and make it work with your ex.

Remember that I am not a therapist, but that I am the real deal. I’ve lived this. There have been times I made mistakes and exhibited bad co-parenting behavior, and there have been times I am proud of the actions I took to effectively co-parent. What I’m saying is, I didn’t arrive here overnight. I messed up at times. That doesn’t make me a bad person, just human.

In closing, effective co-parenting can end up being a really pleasant experience, because even though you are no longer married, you are raising your children together, which is truly what your babies need, and what in the end is fulfilling.

If you are interested in having a better co-parenting situation, you and your ex should audition to be a contestant on NBC’s “Co-parenting 101!” Here’s how:



7 Dating Tips To Turn Your First Date Into Many Many More

Written by Jackie Pilossoph. Posted in dating, dating after divorce, Dating over 50


dating tips




dating tips


There’s nothing worse than sitting by the phone waiting for a guy to call after a first date. Sometimes you never hear from him and wonder ‘what went so wrong?’ In my Love Essentially column, published in Chicago Tribune Pioneer Press, I offer 7 dating tips that will help increase the chances of your next first date turning into a a lot more!

7 Tips To Turn a First Date into Many Many More by Jackie Pilossoph

We’ve all been there. You’re sitting across the table from someone who you think is close to perfect. Smiling from ear to ear, you sip wine and barely eat as you gaze into his or her beautiful eyes, unable to believe that after countless awful dates, you actually met someone who stopped your world.

I’m describing a really, really great first date. Unfortunately, no one gets too many of those, as lots of first dates end in disappointment, irritation, and nightmare stories you end up sharing with your friends. So, how can you turn a first date into many, many more?

With the help of Erika Kybartas, a matchmaker for It’s Just Lunch in Chicago, we came up with seven tips we think will improve your chances.

1. Dress to Impress: “Before you leave the house for any date, look in the mirror and say, ‘Would I want to date me?'” said Kybartas, who has been in the business for 14 years, estimating she has set up thousands of couples during that time, hundreds which have resulted in long-term relationships. According to Kybartas, dress code for a dinner date is jeans, a nice top and heels, or a dress if you prefer. For men, she recommends business casual: jeans, a nice pair of shoes, a button down and sport coat. If coming to the date straight from work, a suit is acceptable. “Look like you put some effort into your outfit,” Kybartas said.

2. Choose the right venue: Keep first dates casual and short in length. Drinks and appetizers, lunch or coffee are great options. Wait for a second or third date to do something more active or that will result in spending a longer amount of time together. Great second or third dates include golf, tennis, a museum, or a paint and sip studio.

3. Be open-minded: “You can’t change a bad personality, but you can always change a bad T-shirt or an unlikable mustache,” Kybartas said. In other words, if you’re a little bit unsure, keep talking! Keep asking questions and getting to know the person. You might just fall in love, and can then talk to him or her about superficial changes later.

4. Talk is important: Good topics for a first date: common interests and lighthearted subjects that make you both laugh. Bad topics: money, finances, religion, politics and past relationships. Also, if you start talking negatively about your ex, or call him or her a name, I can guarantee you will never hear from your date again. Ever.

Click here to read the rest of the article (the other 3 tips) published in Chicago Tribune Pioneer Press!


Friends With Your Ex: Is it Honestly Possible?

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


friends with your ex





Jackie, neither one of us want to get back together, but do people ever talk to their ex’s as friends? In other words, is it possible to be friends with your ex?


When I was in my thirties, living in Boston, I dated a guy for a few months and it didn’t work out. When we decided not to see each other anymore, he said, “I hope we can still be friends.”

I offered a sad sort of chuckle, rolled my eyes and replied, “Yeah, OK.”

Then he said something to me that I will never forget to this day. He said, “I really mean it and here’s why. If two people like each other enough to get into a relationship and then they break up, it makes sense that they would want to be friends. If they don’t, then they never really had anything substantial to begin with. I think we did.”

I have always thought that was a really, really smart way to look at the end of a relationship. Why? Because, if you think about it, you got together with the person because you liked each other. If “like” is present and REAL, it will be there whether you are married, deeply in love, just dating, or broken up.

So, is it possible to be friends with your ex? I’d say it’s IMpossible if you don’t like each other. If it was more infatuation based, lust based, or you loved him or her but didn’t particularly care for them (and that is a very possible scenario), or one of the people did something unforgivably horrendous, I’d say you probably won’t become friends after.

I have no idea how your divorce turned out—if it was ugly, devastating, sad, angry, etc. but the fact that you are talking as friends is a great sign!

So, let’s say “like” is there. Additionally, there are some other factors that could determine whether a divorced couple ends up being friends:


  1. Again, if anything horrendous was done in the marriage or divorce, there’s less of a chance.
  2. If one person really wanted the divorce and the other didn’t, it might be too difficult at first.
  3. If one or both become involved in relationships where the friendship is an issue with the new spouse.
  4. If there are kids involved. (that could bring a couple closer to being friends because they are forced to see each other more)
  5. If one or both are still in love and so there is an ulterior motive of getting back together, then the friendship isn’t authentic.
  6. If the person has a history of divorce (say his or her parents) and doesn’t know how to be friends because they never saw it any other way.
  7. The legal process of the divorce was bad or one person walked away with a settlement they didn’t think was fair.


One really big factor in being friends with your ex is TIME. I think it is difficult to be friends initially, because no divorce or break up ends hurt-free concerning either person. Undoubtedly, one or both are hurting. But as time goes by and the hurt fades, people move on and then I think a genuine friendship can develop. (again, only if there is “like.”)

I will say that if you become friends with your ex, there has to be communication about what the friendship will be, and boundaries established, because it is easy to fall into the old patterns of the relationship, and the bottom line is, it isn’t the old relationship.

Being friends with your ex is a beautiful thing, in my opinion, and a tribute to the relationship you once had. Some people think being friends with an ex is just too weird. Or, they carry bitterness and resentment way too much to go down that road.

But if you can find it in your heart to become friends with your ex, I believe it can be a gift. If you think about it, wasn’t your ex your family? Why would you ever want to turn your back on your family?

Then again, you might be rolling your eyes and saying, “No, thanks, Jackie. I don’t need a ‘friend’ like her (or him.)”

By the way, I am still friends with my Boston guy. It is a gift.



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