This is a TRUE story that I think will help countless single or divorced women dating over 40. It has to do with getting older, body image, self-love, self-esteem, and my girlfriend who needs a good kick in the ass! Last week, she and I got invited to go on our friend’s boat. So she … Read more
As I was walking out the door yesterday morning, heading to the gym, I got a text from a girlfriend that read, “Whatcha doing? Meet for coffee?” I loved it. No planning, scheduling, cancelling and rescheduling, all I had to do was shift a few things around and an hour later (straight from the gym) … Read more
Jackie, I am approaching 50, and just over one year separated from my husband. As I look forward and begin to think about the possibility of future relationships, I can see that dating after 50 might be difficult. I notice that lots of people who were married for maybe 10 years or less seem to … Read more
In my Love Essentially column, published two days ago in Chicago Tribune Media Group papers, I give dating, marriage and divorce advice that could lead to a better love life in 2015, if you’re willing to make these New Year’s resolutions. Try These New Year’s Love Resolutions by Jackie Pilossoph Typical New Year’s … Read more
“How do you know if you love someone is the question I answer in this article in response to a reader: Jackie, I have been dating a woman for four years now. She has a lot of problems with her adult son, who is autistic. He is college educated, but recently lost a job he … Read more
In my “Love Essentially” column published today in Sun-Times Local Media papers, I list 8 great date night movies for football season. The thing is, though, you don’t have to be on a date to enjoy these! They are also awesome movies to watch with a girlfriend or even by yourself! Eight Great Football Flicks … Read more
Did you happen to hear about that company in England that owns a bunch of dating websites, and was charged with making up phony profiles? Well, the story motivated my “Love Essentially” column, published yesterday in Sun-Times Media local publications. Tips for a Safer, Better Experience on Dating Websites, by Jackie Pilossoph Dating websites really have … Read more
It’s kind of ironic. You get divorced and you don’t think anything can be worse. Until…the heartbreak of your next relationship. The pain you are feeling can seriously feel physical. I have had chest pain after a breakup. And read this woman’s email to me. She’s saying “It’s hard to breathe!” I’m a 35 year … Read more
In my “Love Essentially” column, published yesterday in Sun-Times Media local, I offer relationship advice as it pertains the upcoming “Sweetest Day” (which is tomorrow.) Not particularly a fan of Sweetest Day, here are some really “sweet” things you can do for your spouse that don’t involve sugar, and that won’t cost you a dime! … Read more
A DGS reader asks: What do you think I can do to draw a healthy, stable, loving relationship into my life and stop dating losers? Is it me, or is this a nicer way of asking, “How can I avoid picking complete losers and meet someone who is normal and who treats me well?” In … Read more
What would you do if you found a great guy (or girl), who you adored, and who your kids LOVED, but when it was just the two of you, you had zero interest in taking your clothes off? In other words, there was no passion. That’s what I address in this week’s “Love Essentially” column, … Read more
In my Love Essentially column that came out today in Sun-Times Media Local, I talk about reasons why men and women rush into relationships, and why rushing into relationships isn’t always wise. What baffles my mind, even more than single people rushing into a relationship is when divorced people do it. I really just don’t … Read more
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