Jackie, I’m wondering if you can write about dating as a single mom when your ex is especially difficult. In any divorce, when you think about dating again, you get overwhelmed, but what if you add to that worries about your ex actually trying to sabotage any attempt to move on, just to “get even.” … Read more
Dating a single dad can be complicated. It can make you feel sad, frustrated, infuriated and can possibly drive you crazy, at times. Why? Because there are so many different relationships going on at the same time, and some or all can be intense and sensitive and complex. Let’s look at the dynamics of dating … Read more
You got divorced and began dating. You never thought you’d meet someone you’d fall in love with again. And then you did!! Things couldn’t be better. You’ve never been happier. So, how do you stay happy? Here is my advice for a wonderfully healthy relationship, and how to not get dumped. How to not get dumped … Read more
One of my friends recently began online dating after divorce. She met a guy on Bumble a couple weeks ago and they went out last weekend. Turns out, it was a pretty bad date. I tell her story and offer my advice in this week’s Love Essentially. When Did Men Stop Being Gentlemen? by Jackie … Read more
Here’s some dating advice that comes in the form of question to ask on the first 3 dates. These questions will help you determine if you’re truly ready to go after your goal of having a long-term, successful relationship. Picture this: You’re on the 3rd date with someone you really like – and who seems … Read more
Here is an email from a reader seeking advice about getting mixed signals from a girl. He is seeing a woman who is 7 years older than he is. The two have known each other for awhile, and she reached out to him when she heard he was divorced. After she had reached out … Read more
Ladies, fess up. Are you dating a nice guy but not attracted? Maybe he didn’t do anything for you physically? He called when he said he would, confirmed plans, was a gentleman…but nothing in the feelings department. Nada. Zero. Zilch. So you go from dating a nice guy but not attracted to dumping the nice … Read more
Summer is upon us! It’s a time for pools, barbecues, vacations, and adventure. Typically in the summer months, things tend to slow down a bit and we find ourselves with more time on our hands. That’s why the summer is the perfect time to start dating and focusing on finding the one. Having time to … Read more
It’s not unusual for clients to begin my relationship coaching program in a somewhat fretful state and looking for a relationship. Having spent years devoted to their careers, they eventually came to see the lack of balance in their lives. Some name what they feel as an inner emptiness. Others describe their lives as … Read more
Are you an underdog when it comes to dating and relationships? In this week’s Love Essentially, I explain what exactly it means to feel like an underdog in love and relationships, and I offer dating advice for underdogs who want to be smart, and find and sustain healthy romantic relationships. Are you the UMBC … Read more
When I realized that the 5th year anniversary of Divorced Girl Smiling, (my divorce advice site) was approaching, I decided I wanted to do something really special, meaningful and important. So, I decided to throw a huge party, and make it a fundraiser for WINGS, an organization that offers shelter, support and education to victims … 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
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