Derek Rake Insider

"Hey, my relationship has some new developments that require me to ask something. Basically, I learned that my girl has had a bad sexual past and she said that I was being too pushy and demanding by trying to escalate things. I don't know why she waited to tell me about this. (Btw, she's a virgin.) … [Read More...]

"A lot of the time, I see attractive women with members of their family, such as their mother. I want to go up to them, but how can I approach this particular situation? And how do I deal if I get rejected in a bad way? Cheers and great stuff!" - William H. from Hardisty, AB Derek Rake's … [Read More...]

"Hi Derek. I haven't checked my email for several weeks and I have a question for you. As of late, I have transcended my personal approach anxiety. I'm 31, after all, so I figured it was time to. However, I now have a huge problem: how can I transcend my shark vibe or neediness? I have come to … [Read More...]

"I like this friend of a friend who's a model, but I don't have a car, a job or money; I live in a dinky apartment; and I'm not even studying just yet (though hopefully will be in the following semester). This is why I have trouble talking to her a lot of the time. I kind of feel like she should be … [Read More...]

"My question has to do with this girl that I proposed to several months ago. She said she was dating somebody else that time, though. She's the kind of girl who loves to give excuses each time I ask her out. However, there's this one thing that I love about her: she tries to call me over the phone … [Read More...]