This category contains articles about dating relationships and sex.
Jackie, I need some relationship advice. What is a better relationship? Comfortable and good enough, where your life is generally better but you’re not exactly in a rush to see the girlfriend or “Head over Heels in love:” where there is a ton of passion but that’s the only thing notable. My gut reaction … Read more
If you are dating a playboy or you aren’t sure, this is a great article for you. Published today in the Chicago Tribune Pioneer Press, this week’s Love Essentially is about playboys and why women either love them or why they run from them. Enjoy! How Do Women Really Feel About Playboys? by Jackie Pilossoph for … Read more
Read my advice column, Love Essentially, where I offer advice to a woman having marital problems due to her sister-in-law, who is living with them. Three Is A Crowd For This Married Couple And His Sister by Jackie Pilossoph for Chicago Tribune Pioneer Press Marriage isn’t easy. Just ask a married person. Even the happiest of … Read more
This is a piece I wrote, intended for young women who think they found Mr. Right and who are now waiting for him to pop the question. 12 Tips For Women Waiting For That Perfect Diamond Ring by Jackie Pilossoph for Chicago Tribune Pioneer Press From the time we are little girls, women are shown … Read more
This single dad dating needs some help. Read his story and feel free to offer him your advice! I’m 33 and a single father. My wife left me for a woman. I find the dating game terrifying, with Tinder, Snapchat and all the latest dating tools I don’t understand. My confidence is shattered and I … Read more
I recently began tracking my kids’ phones and it got me thinking, if I was married, how would I feel about tracking my husband’s phone? One one hand, tracking a spouse’s phone would probably give a person peace of mind. On the other hand, it could create all kinds of trust issues. “Why were you … Read more
I’m going to give you the story in a nutshell. A divorced woman has been officially divorced for a little over a year after a 20 year marriage. They had some financial and other issues and he refused to go to counseling. She said he is a good dad, but she felt nothing for him. … Read more
I’d have to say most divorced women I know have experienced one or more cougar relationships, or if they haven’t, they want to. I myself had a relationship with a man who was 13 years younger than me when I was a newly divorced woman several years ago, and I have to confess, it was … Read more
In honor of Mother’s Day, I thought I’d address a reader’s comment. It comes from a caring daughter who is worried about her mom being lonely, and wants to know how she can help her. My mother is almost 60. She’s been single for 8 years now. I know it’s because she is nervous … Read more
I have a dating tip that has to do with what I call “gift wrapping yourself.” What I mean by that is, you and your first date could really really be right for each other, but he or she never got past the fact that there was no physical attraction. Not because you aren’t good … Read more
A friend of mine was telling me that he recently went out for some drinks with a group of his buddies. All the guys are over 40 and all married with kids except for one guy, who is divorced and recently remarried. My friend explained that although all the guys were very happy for him … Read more
When it comes to offering divorce and dating advice, the most common question I get asked is, “How do you meet normal guys/women?” People who are dating after divorce all constantly telling me how hard it is and how everyone who is on dating sites are losers and they can’t take it anymore. The ironic … Read more
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