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Articles by Jack Heart

About Jack Heart
Jack is a wise but curious figure whose exact whereabouts and identifying details remain unknown. What we do know is that he's really, really good at matters of the heart. He’s been on more dates than you can imagine, and he’s here to help other guys step up their game.
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ashamed of size
Dating Tips

I’m Ashamed of My Equipment Size and It’s Ruining My Love Life

December 6, 2018 Jack Heart

When you are embarrassed about your equipment size HIS QUESTION Dear Jack, It’s taken me a long time to write this note because it’s so embarrassing. Perhaps the best way to do this is to […]

couple intimacy communications
Dating Tips

How To End an Extramarital Affair with a Coworker

November 24, 2018 Jack Heart

You’ve been having an extramarital affair a coworker HIS QUESTION Dear Jack, I never thought I would admit this but here it goes. I’ve been having an extramarital affair with a coworker for the past […]

condom cheating
Dating Tips

If She Insists on a Condom, Is That a Sign of Cheating?

October 3, 2018 Jack Heart

You are both exclusive, but she still wants you to wear a condom Jack offers answers to tough questions men want to know about love, romance, and relationships. His Question Hi, Jack, I’ve been dating […]

Libras - men in love
Dating Tips

What to Do If She Dumps You and Then Wants You Back

September 24, 2018 Jack Heart

She dumps you and now wants to get back together She’s gone forever…no wait, she’s back again. Your girlfriend dumped you, but now she wants you back. Is it time for a victory lap or […]

meeting parents over coffee
Dating Tips

Meeting Your Girlfriend’s Parents Do’s and Don’ts

September 22, 2018 Jack Heart

Meeting your girlfriend’s parents? Here’s some tips! “His palms are sweaty, knees weak, arms are heavy There’s vomit on his sweater already, mom’s spaghetti He’s nervous, but on the surface, he looks calm and ready” […]

men's cologne bottle
Dating Tips

Is Wearing Cologne on a First Date OK?

September 22, 2018 Jack Heart

When you aren’t sure if it’s OK to wear cologne. HIS QUESTION Hi, Jack, This may sound like a silly question but here it goes. I am wondering if it is OK to wear cologne […]

gemini man with a woman
Dating Tips

How To Approach a Woman You Don’t Know with Confidence

September 8, 2018 Jack Heart

Want her number? Here’s how to get it Struggling with how to approach a girl and ask for her number? Hoping to break the never-ending cycle of chickening out and regretting it later? Need some […]

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