He’s turned 27 and regrets what he hasn’t done with his life. How can he make up for what he missed and ensure he doesn’t stay stuck in a rut?
Archives for May 2026
How Do I Get A Date Without Asking For A Date?
Everyone says to be direct when asking someone out, but asking for a date feels clunky and never works for him. What’s the right way to ask someone out?
My Boyfriend’s Gone To College And I’m Afraid I’m Being Left Behind!
Her boyfriend is off to college. She’s got a year left of high-school. How can she stop feeling like she’s being left behind while he’s off having new adventures?
My Friend Tricked Me Into Going On A Date!
She thought she was having lunch and catching up with an old friend… until he told her that it was a date. How is she supposed to trust him now?
Who Gets To Define The Break Up?
Their ex was toxic and controlling. Now, he’s trying to control the story of their break up. What should she do? Who gets to define a break up?
Help, I Don’t Know What I Want From Dating, But This Isn’t It!
He’s been going on dates, but always with the wrong people. How do you date when you aren’t even sure that you’re looking for the right things?
