dating after 50

Women Dating After 50: Are We in No-man’s Land?

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

Are Sweatpants a Cause of Divorce? Indirectly, yes.

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 … Read more

Divorced Girl Smiling Dirty Dancing: The Time of My Life

I think it was about a year ago, while watching my son’s basketball game that one his friend’s moms came up to me, told me she was the co-chair for the 2015 Glenview Education Foundation fundraiser called “Dancing With the Local Stars” and asked if I would be willing to be a contestant. My initial … Read more

Dating, Marriage and Divorce Advice for a Better Love Life in 2015

      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

Eight Great Date Night Movies For Football Season

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

Dating Websites: 5 Tips to Make Your Experience Better & Safer

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

Relationship Advice: 15 Ways to Be Sweet that Don’t Cost Anything!

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

Relationship Advice: Common Interests Lead to Happy Couples

In this week’s “Love Essentially,” published yesterday in Sun-Times Media local, I give relationship advice that has to do with the importance of a couple’s commonalities.  The column starts with a letter I received: Dear Jackie, I love playing in the Buffalo Grove Symphonic Band. Apparently, so do others, including six married couples! One couple … Read more

Hooking Up With Your Ex: Appealing? Or No Way?!

Everyone I know says they’ve heard of couple, who on the day their divorce was finalized, went straight from the courthouse to a hotel room, where they secretly met up and had sex. Sounds like a great movie scene, but in reality, I’ve never known anyone who actually told me firsthand that he or she … Read more

Divorce Advice We Can Take Away from Ray Rice

I don’t think there is anyone on this earth whose jaw wasn’t on the ground after seeing yesterday’s newly released video of Ray Rice punching his then fiancé (now wife) Janay in the face in an Atlantic City Elevator last February. But for me, even more shocking is learning that Janay married Rice AFTER that … Read more

dating losers

How to Stop Dating Losers and Meet Someone Meaningful

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