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It sucks being jerked around by your heart strings

“A while ago, you helped me with a question involving my relationship. You were extremely helpful and right. I was hoping you may be able to do it again.

long story short:
This girl and I started dating in high school for 1 1/2 years. We were each other’s firsts. She then broke up with me because [...]

Dating and Relating

“I am 18, and a bit of a loner. I have never been in a relationship of any kind, and I’d just like to ask how the entire process works.  I have girl friends, of course, but it’s the all important space between the words. As a bit of background, I am a geek, smart, [...]

Coming Together and Maybe not With Others

“My boyfriend and me were able to cum at the same time for the first time yesterday. I really liked it but it has never happened before. In order for me to cum I have to have intense stimulation of my clit so I used a electric toothbrush on my clit while i am in [...]

Crossing Boundaries with Friends and then Trying to go Back

“Dear Shay,
Before I start, wanted to say that I love your column. Its a great source thats entertaining and informative. Now onto the crux of the issue. I have a friend whom I met at college. One night we were hanging out and (after too many shots of whiskey) we start making out on the [...]

Bedroom Trades

I recently posted some ideas for a reader who wanted to know how she could get her partner to give her want she wants in bed…

And that got me thinking.

How do you get what you want in bed?

Do you try to subtly hint?
Do you demand?
Do you turn [...]

Getting What You Want In Bed

“I have three questions. I’ll be straight and to the point, then provide background. Alright? Here goes.  My boyfriend is a little dense when it comes to sexual things, what’s the best way to go about teaching him?  And two, do scratches in the va-goo heal quickly, or would they easily be infected?  And the [...]

Yes, Friend Zones Exist Online

“Hi, Shay. this is alil off from ur ussal questions. But ur the only person i thot would have an idea. About a year ago. I tried internet dating. Past relationships hadn’t worked out. Due to my faults or theirs.Anyway. Me and my gf met on a site. started talking n such. Finaly decided [...]

Looking for More than Casual Sex

“Hey shay, I first found your site about a year ago and have been a casual visitor ever since. I have thought about asking you for a few pointers, but I really didn’t have a question that couldn’t be answered by your more general suggestions until now. OK, this may seem strange, but I need [...]

Dating Friends and Friends of Friends

“I have a relationship question for you.
Ok, I have my best friend Julie*, and her ex boyfriend’s name is Troy. Troy is my best friend, and my recent ex-boyfriend John’s, best friend. My problem is I’m really attracted to Troy, so Troy and I were talking about casually dating. Which sounds fine because its fun [...]

Happy Pride!

June is Gay (or LGBTTQQA*) Pride Month
and the whole city of Toronto is gearing up for this weekend’s HUGE pride celebrations!

(You can even follow the updates on Twitter!)I checked it out last year and it was INSANE!
MILLIONS of people showed up for the Pride Parade.
Church street was shut off to traffic [...]