Articles by Jack Eagle

When you are attracted to your ex’s twin HIS QUESTION Dear Jack, Recently, I started casually seeing a girl that I really like. We seem to hit it off on many different levels. Sounds like […]

Your partner wants to take a break from the relationship THE PROBLEM Hi, Jack, I’m desperate here. My boyfriend of a year said he wants to take “a break.” He’s been super vague about why […]

Your girlfriend wants to record a private video The Dilemma Hi, Jack, I’ve been dating a girl for around six months now and really like her. The only thing is that recently, she’s been hinting […]

Do you project a toxic vibe? Have you decided to hit the pause button on dating because you’re tired of rejection? Does it seem like your first dates never turn into second dates? Are you […]

Dilemma: Can You get back into the Hot Zone after your partner has given you the cold shoulder? His Question: Me and my boyfriend for 6 months are going through a break (or breakup?!) We […]

The Dilemma Dear Jack, I’ve been dating the same girl for the past month. A few nights ago, we finally became intimate, with both of us under the sheets. After we finished, I couldn’t help […]

You aren’t a social butterfly, but you want to make the most of your latest party invite. The Dilemma Dear Jack, I’m a nineteen-year-old guy living in a college town. In high school I was […]

You really enjoy having sex with your girlfriend but don’t see any other value in the relationship The Dilemma Dear Jack, I’ve been with my girlfriend for a few months now. I’m not gonna lie […]

Do Older Women Make Better Partners? THE PROBLEM Hi, Jack, I’m 29, straight and single. I’ve dated a few different types of girls, but I’ve never dated an older woman before. I usually date women […]

What to do after breaking up Have you recently broken up with someone you deeply love? Are you struggling to hold things together? Wish you had a magic wand to make the pain go away? […]