21 Dating Tips I wish I could Have Shared With My 21 year-old Self

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July 17th, 2014 . Jackie Pilossoph

When I was 21, I had my whole life ahead of me. I felt unafraid of almost anything. Physically, I felt wonderful. I was free-spirited and happy most of the time. All that said, at 21, I was so naive, I made so many mistakes, and I didn't have wisdom,...

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We’re Into Each Other! So Why is His Profile Still on Dating Websites?

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July 10th, 2014 . Jackie Pilossoph

In my "Love Essentially" column published today in the Sun-Times Media local publications, I respond to a reader's e-mail regarding a guy she met on one of the dating websites, who she really likes. There's one red flag: his profile is still acti...

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How to End a Relationship on Good Terms with the Prince Turned Frog

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July 3rd, 2014 . Jackie Pilossoph

When I got an email from a reader asking how to end a relationship on good terms, I immediately thought of the famous post it note that Berger gave Carrie on Sex and The City. that read "I'm sorry, I cant. Don't hate me."   [CTA-Ad-Trusted] ...

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Let’s Talk About Sex After Divorce–Safe Sex, That Is

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June 29th, 2014 . Jackie Pilossoph

Divorced Girl Smiling received this e-mail from a reader seeking advice about sex after divorce and how to be safe. I went out with a guy a couple of times and we really hit it off. Our relationship quickly became physical and in the heat of the m...

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Dating a Coworker is Sexy but Not Always Wise

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June 27th, 2014 . Jackie Pilossoph

There’s nothing more romantic than sneaking into a supply closet at work with your new boyfriend or girlfriend — who is also your coworker — to start kissing. Your secret relationship from the rest of the office is sexy, exciting and fun. But, ...

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