Author: Jackie Pilossoph

'Love, Simon' represents a turning point in high-school romance genre  by Jackie Pilossoph for Chicago Tribune Media Group I have often thought about how unbelievably difficult it must be for a gay teenager to come out. It’s challenging e...

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...

Thinking about taking off your wedding ring? Or, did you recently do it? Did your spouse take off his or her wedding ring? Taking off your wedding ring means...what exactly? People take off their wedding rings for all kinds of different reasons. G...

It might be one of the biggest gripes divorced women have: when you're dating a man with kids and feeling left out. Several years ago, I was in a relationship with a divorced guy who had a 13 year-old daughter who refused not only to meet me, but ...

'The Bachelor' Breaks The Mold in All the Wrong Ways by Jackie Pilossoph for Chicago Tribune Media Group Typically, I might use the words "predictable," "scripted" and "formulaic" to describe the final rose ceremony of "The Bachelor."   ...