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Dating Advice: 8 Tips For Striking Up a Conversation Without Striking Out

Written by Jackie Pilossoph. Posted in Uncategorized


dating advice

dating advice


In my Love Essentially Column, published today in the suburban Chicago Tribune publications, I offer dating advice on ways to strike up a conversation, in other words, pick-up lines that aren’t cheesy!


Pick up Lines Don’t Have To Be Cheesy by Jackie Pilossoph

Ever been in this situation? You’re out at a bar or restaurant and you see someone you find attractive, and who you’d like to meet. The problem is, you don’t know what you could possibly say to the person that doesn’t sound rehearsed, stupid or just plain old cheesy. You fear that whatever you come up with, the person will think you are desperate or strange. So, you do nothing. He or she ends up leaving, the opportunity is missed and later that day or night, you’re kicking yourself for not making a move.

Approaching someone and or delivering an effective opening line (also known as a pick-up line, let’s be honest) isn’t easy. But if what you say is effective, your reward can be priceless: the beginning of an exciting, new relationship that may lead to the end of your search for Mr. or Ms. Right.

Even as a dating and relationship columnist, it’s difficult for me to offer advice on how to approach someone and what to say. As outgoing, friendly and full of words as I am, I turn into a complete mess when put under pressure to start a conversation with a cute guy, trust me.

So, I recruited the help of Barbie Adler, founder and president of the Chicago-based matchmaking company, Selective Search. I first asked her why men and women have such a difficult time approaching someone they want to meet.

“Everyone has a fear of rejection and they don’t want to set themselves up for failure, having their feelings hurt or being embarrassed in front of their friends,” said Adler, who started Selective Search 15 years ago. “Everyone knows all the cheesy pick up lines and no one wants to use one because that’s not who they are. They don’t know how to go about it while being their authentic selves.”

Here are Adler’s eight tips for success when approaching a potential romantic interest:

1. Get your head out of your phone. The only reason to have your phone out during a night out with friends is if you have children who might need to reach you. Otherwise, be engaged in the evening and focus on the environment. In other words, don’t be on Facebook and other social media sites, and stop texting all your other friends. It’s a turn off! Put your phone in your purse or pocket and forget about it!

2. Women: smile and be approachable. When a bunch of women go out for a girl’s night, they don’t realize that a large group can be intimidating and overwhelming to men. So, if you see a guy checking out your group, smile at him. Let him know it’s OK to come over and say “hi.” Or, what’s wrong with YOU walking up to him and starting a conversation? Nothing!

3. Compliments are never out of style. But, they have to be sincere. Also, it’s better to compliment shoes or a handbag or a smile versus a dress or the woman’s body. It’s more respectful.

4. Direct can work well. “Hi, I’m Dave, may I buy you a drink?” Simple and honest. No games.

5. Try situational humor. Let’s say you’re in a really long line at Starbucks and there’s a cute guy in front of you. Say something funny about the line. Be friendly, witty and smart. Click here to read the rest of the article published today in the Suburban Chicago Trib papers.  (3 other great tips)!


Divorce Advice: Read Every Line of Every Document You Sign

Written by Jackie Pilossoph. Posted in divorce advice, divorce process, newly separated


Divorce Advice


I want to offer some divorce advice that I believe could make a big difference in your life, and it has to do simply with READING the divorce documents you sign. So, READ on!

I don’t know about you, but if I go to the doctor for something and the doctor writes me a prescription, I go get it filled, read the directions and start taking it. In other words, I don’t question it. I don’t read and analyze every word on the package insert. I might skim it, but if it’s a doctor I really trust, I just do what he or she says. And so far, in my over four decades of life, it’s worked for me.

So, when I was going through a divorce, and my attorneys told me to sign things that they prepared, I pretty much did the same thing—skimmed it over, trusted them, signed the documents and was done.

BAD, BAD, BAD way to do things. Here is the best advice I can give you: KNOW EXACTLY WHAT YOU ARE SIGNING.

One of my best friends is an attorney, and ironically, when it comes to business, if someone gives me a contract to sign, I always send it to her to have a look.

This is what I love about my friend (who by the way is one of the smartest people I know.) She will call me up and say, “Ok, paragraph 3, point number 2A basically says that if you hate working with this guy, and you change your mind and don’t want to work together anymore, you cannot get out of the contract. Is that ok with you?” She then goes through every single point of the contract and spells out in ENGLISH what exactly I am signing. Why? Because I don’t speak lawyer!!!!!

So, in my divorce, I didn’t send the docs to my attorney friend. I trusted my attorneys and signed the documents they prepared without really understanding what I was signing, because I didn’t know what half the words meant!

Do you know what the following terms mean?

Petitioner, respondent, dissolution of marriage, discovery, jurisdiction, marital settlement agreement, petition, order, collusion, custodial parent, motion, temporary support, writ of summons

When I was newly separated, reading documents with these terms in them was like reading Chinese. And back then, I wish my attorney would have sat down with me, (like my best friend does) and explain exactly what these were. He just assumed I knew. Furthermore, you might say, “Well Jackie, why didn’t you educate yourself? Why didn’t you research the terms and read the docs thoroughly until you understood them?” Know why? Because with everything else I had going on in my life: being there for two small kids, job searching, coping with my emotions, figuring out finances, trying to deal with my ex, and a million other worries, I didn’t have time to take a crash course in law 101. AND, for what I was paying my attorney, he should have taken the time to do what my best friend does.

The whole point of this article is, know what you are signing because even the smallest thing—just a few words—could make a big difference later on. That’s all I’m saying.

Plus, once you learn lawyer language, reading documents doesn’t take as much time. The point is to learn it. Don’t be afraid to say to your attorney, “I have no idea what this means. Can you tell me in English exactly what I am signing?”

No one will think you are stupid. Trust me. I have a masters degree and I couldn’t figure it out, same as one of my best friends who is a neurologist and doesn’t understand what the Dow Jones industrial average is.

We all know our field. Why on earth would we know divorce law unless we had to go through it ourselves?

In closing, I’d like to say that I am not telling you not to trust your attorney. You could have the best lawyer in the world, which I hope you do. What I’m saying is, be empowered by getting educated, so that there are no surprises in your future when your divorce decree needs to be pulled out of the drawer because your ex isn’t doing what you think he or she should be doing according to your decree, and then you say “Wait a minute, doesn’t it say that he can’t do that?” And according to your degree, he can.

There is nothing more empowering than knowledge. Remember that, and take the time to thoroughly understand what the pen in your hand is about to help you sign. Ask your attorney about every possible scenario: lots of “what if” questions. If you do that, the surprises that come with life have so much less of a chance of having a negative impact on you. To put it bluntly, you will have covered your *ss!

Divorce Advice for Fear

Written by Jackie Pilossoph. Posted in coping with divorce, divorce advice, divorce anger, newly separated


divorce advice

There are so many feelings that come with being newly separated and going through a divorce: shock, guilt, devastation, sadness, anxiety, anger, jealousy, bitterness and…one of the worst—FEAR. That’s why I decided to write a piece offering divorce advice just for fear.

Fear is a very powerful emotion that can cause a lot of pain, along with a lot of other issues, both physically and emotionally. As a newly separated woman at 41, who hadn’t had a job in five years, I can remember being incredibly scared for a long time. Of what?


  1. my financial future
  2. my kids and issues they were having
  3. loneliness and isolation
  4. growing old alone
  5. the divorce process (judge’s rulings on custody and financial issues
  6. attorney’s fees
  7. living alone with two kids.
  8. what people were saying about me (the single mom in the suburbs)
  9. how angry my ex seemed
  10. dating again and all the weirdos out there.


I think it is very normal and understandable to have fear, but how you choose to handle it is very important in how your life will be and how it will end up.

Beware: fear can lead to some bad things if you let it. Such as:

1. Anxiety and stress that can lead to physical symptoms: such as ulcers and other digestive issues, depression, weight gain, insomnia, irritability (mood swings), poor immune system/illness.

2. Anger. I believe anger is driven by fear. Good rule of thumb: if your ex is angry, he or she has fear about something. If you understand that, you will have empathy and not be angry back.

3. Bad decision making. Maybe you are afraid of your ex, so you make decisions to try not to anger him or her. Or, fear can hold you back. Maybe you don’t take a new job because you are afraid of failure, or even worse, you don’t look for a job because you are fearful you won’t be able to handle it.

4. Lack of self-love. People who let fear rule the decisions they make don’t like themselves that much because they don’t have self-respect.

Now, here are some positive things about fear:

  1. Fear causes motivation. I recently received a text through Cyber Dust from Mark Cuban, saying that fear has caused him to work harder and become successful. If you are afraid of not being successful, it could motivate you to work harder and smarter. Fear of financial problems often motivates people who work on commission and in countless people I know, it made them extremely successful and wealthy (like Mark Cuban.)
  1. There’s nothing like the feeling of overcoming fear. There is no better self confidence booster than thinking to yourself, “I’m not going to be afraid anymore.” Not being afraid of something you used to be afraid of is THE BEST feeling. It’s so empowering, so freeing, and it makes you proud of yourself, and gives you self respect and self-love.

I recently went through something that was causing me a lot of fear. Because of that, I cried a lot, I felt anxious, and it felt a bit paralyzing in my decision making.

How I handled it was: I cried a lot—until I couldn’t cry anymore, and then my skin got thicker and I felt like a boxer in training. I educated myself, I thought through things clearly, I did some yoga, I focused on having gratitude for good things in my life, and I had conversations with some people I needed to straighten things out with. I did what had to be done without letting fear stop me.

It was an amazing feeling. I loved myself for it. I felt strong and it made my problems seem really manageable.

And when I showed up to rehearse with my dance partner last week, (for an upcoming show I am performing in) I looked at him and said “I’m ready,” and he knew exactly what I meant. For weeks I’ve been really scared to do the lifts in our programs. It was a terrible feeling. It was almost ruining the experience. But then I thought, ‘If I can handle all this other crap I have going on in my life, where the fears are so much larger than being afraid to let my fit, young, strong dance partner lift me in the air, it’s time to relinquish control and just do it.’ So, we danced. And he lifted me high off the ground and he spun me around. And I wasn’t scared. Why? Because I decided not to be. And I loved it and looked darn good!

I’m not saying that you are wrong for having fear. Fear in divorce is very normal and to be expected. What I’m saying is, find a way to manage your fear in a productive way. In other words, find a way to do YOUR lifts! Because once you aren’t afraid, you will make better decisions, you’ll like and respect yourself a lot more, and you’ll be a happier person.




Advice for the Really Really Newly Separated

Written by Jackie Pilossoph. Posted in divorce advice, divorce process, My Wife/Husband left me, newly separated

newly separated  newly separated

The following Love Essentially column, published yesterday by Chicago Tribune Media Group offers great advice for the newly separated man or woman, and I mean REALLY newly separated-like, your spouse just said “I want a divorce.” Now what? Read this. It will help you.

What to Do If You hear, “I Want A Divorce” by Jackie Pilossoph

There’s something just as cold as the Polar Vortex that comes with January: divorce filings.

I’m pretty sure that’s the reason January is National Divorce Month. It’s the month that statistically, most people file for divorce.

“People don’t want to get divorced right when school starts, and then it gets close to Thanksgiving, and they don’t’ want the holidays to be remembered as the time they got divorced, so we have a huge number of people who come to see us after the first, when they feel it’s a better time for themselves and for their kids,” said Karen Pinkert-Lieb, a senior partner at Schiller DuCanto & Fleck, who has been practicing family law at the firm for more than two decades.

I sat down with Pinkert-Lieb to ask for advice on what you should do if you recently heard the words, “I want a divorce,” and have been handed divorce papers. It’s a moment that can cause devastation, confusion, fury, fear, and shock to the point where you’re standing there with your mouth open thinking, ‘What the heck just happened?’

Pinkert-Lieb recommended that the first thing to do is to find an attorney, and then offered four tips for the best search methods:

1. Publications that rate attorneys: She recommended three websites, all that rate attorneys based purely on legal ability and ethical standards: Martindale-Hubbell, Best Lawyers and Leading Lawyers.

2. Word of mouth: Ask friends or professionals, such as accountants, other attorneys or therapists for recommendations. Also, it’s helpful to get direct references. In other words, talk to the clients to hear their experience with the attorney.

3. Learn as much as you can: Google the attorneys you are considering to read their bios and find out if they are a good fit for you. Are they litigation focused or do they lean more towards mediation for clients? Who is their clientele? Do they handle high net-worth clients? What is their niche?

4. Meet with the attorney: “This is a relationship that is intimate,” said Pinkert-Lieb. “You will be spending a lot of time with this person and you have to feel a certain chemistry, and feel like you can trust and have confidence in that person.”

After obtaining an attorney, Pinkert-Lieb explained that it is important for that person to educate you about the judge who gets assigned to your case. Why? Click here to read the rest of the article, published yesterday by Chicago Tribune Media Group.


Divorce Advice: Guess What? Your Ex and His New Wife Aren’t As Blissful As they Are in Your Head

Written by Jackie Pilossoph. Posted in coping with divorce, My Wife/Husband left me, newly separated


divorce advice

I ran into a friend a few days ago who told me a story that I thought was truly worth sharing, as it translates into great divorce advice.

This friend of mine was happily married (or so she thought) for over two decades. A few years ago, her now ex unearthed her by asking for a divorce, and then marrying the woman he was cheating with, just days after their divorce was final.

It was a tough road for my friend. I watched her go from rock bottom at day one, trying to absorb the shock, through all the phases that included tears, depression, furry, fear, bad dates, confusion, to where she is now: a happy, healthy beautiful, successful person who is very much in love with a great guy.

Now, what about her ex? Here is the important story. My friend went on the woman’s twitter account the other day. Ok, I know that might seem a little stalkerish, but I actually don’t see it that way. I call it curious. Trust me, I’ve seen way worse when it comes to men and women stalking their ex’s. This was harmless. So, anyhow, she saw all the people the woman followed on Twitter, and noticed that she follows 10 cheating sites! Sites that include information like, “how to catch your husband cheating,” “What to do if you think you husband is cheating,” and “signs he’s sleeping with someone else.” The woman was also following several sites that were in the town where my friend lives. Why is she following our town when she lives 500 miles away? Very strange. Is she checking up on my friend?

The reason this is important to share is because I get so many emails from women (and men) whose spouse left them for someone else, and they paint this picture in their head that everything is blissful with their ex and his new spouse. NOT THE CASE my friends. Here is a woman who willingly began an affair with a married man, stole him from the wife, and is now suspecting that he is cheating on her. That doesn’t sound very blissful to me.

I am of the opinion that any relationship which starts with lies and cheating has a huge chance of failure, long term. Why? Because eventually, the burden of the guilt associated with what you did catches up with you and it damages the relationship. The person ends up with such self-hatred that they either take it out on the new person (like it was his or her fault for participating in the cheating) or they cheat again.

That’s just my theory. I don’t want to generalize, and I am sure there are countless men and women who technically cheated, but whose marriages were totally over. In other words, they hadn’t slept with their spouse in years, were disconnected, etc. Not saying that cheating in any case is acceptable/excusable—maybe those people should have left first. But, I’m not judging them. It’s the ones who decided to cheat, who were still sleeping with the spouse–who didn’t even know there was a problem. That’s where I have issues.

My friend also asked, “Have you heard that Kellie Pickler song, ‘Best Days of Your Life?’ I feel like that song describes my life exactly!”

I hadn’t heard the song, so I looked it up and listened to it, and the message I got from it is something I think will help men and women whose spouse left them feel incredibly good! Here are some of the lyrics:

“It’s just too bad you already had the best days, The best days of your life,”

“Ain’t it a shame, A shame that every time you hear my name brought up in a casual conversation you can’t think straight?”

“And ain’t it sad, you can’t forget about what we had? Take a look at her and do you like what you see Or do you wish it was me?”

“And does she know Know about the times you used to hold me, Wrapped me in your arms and how you told me I’d be the only one?”

“Someone told me once when you were out She went a little crazy, ran her mouth about me Ain’t jealousy funny?”

“Life with me was a fairytale love, I was head over heals ’til you threw away us”

“I heard you’re gonna get married, have a nice little family
Live out my dreams with someone new
But I’ve been told that a cheater is always a cheater
So I’ve got my pride and she’s got you.”

The bottom line is, if you are the first wife (or husband), your ex’s new spouse will always feel just a little bit second class. That’s my opinion, right or wrong.

They will also always know in the back of their mind that they hurt an innocent person. They keep that guilt and shame locked away in a remote part of their core, thinking it will eventually stop bugging them, but it never does.

Even if they tell everyone things like, “From what I heard, she was a bitch, she was mean to him, he never really felt understood by her, she’s psycho and can’t understand that he just doesn’t love her anymore,” etc. etc. , In the back of their mind, they know what they did was morally wrong. So, wouldn’t you rather be YOU than her or him? Because, when YOU meet someone and fall in love again, your relationship will have started off without dishonesty, and without having hurt anyone. It’s a beautiful beginning, not a tainted, scummy one.

I’m sure it really really hurts to be left for someone else, but the bottom line is, don’t assume that he or she is going to live happily ever after. Their future is baggage filled. Yours, on the other hand is wide open!


Coming Soon!



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