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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 [...]

Yet Another Reason Why Stereotypes are Bad

“hi shay, Do all men have high libido’s and what is a normal level for a man?
I’m asking because my husband doesn’t seem to want to have sex as much as me and when i ask him if he wants to have sex he almost always says no which is a shocker to me cuz [...]

Being Safe? Oh It’s Worth It

“Hi Shay. Me and my girlfriend want to have sex soon but I realised getting a condom would be a bit of a challenge. How do most people my age, 18, get them? I dont really want to go into the supermarket and buy a pack like that, its a bit embarassing. Thanks“

I’m sorry, there [...]

What If I Don’t Want to be the Sex DD?!

This past weekend, I got together with some friends for a movie night.  One friend insisted that we watch 100 Girls, because he hadn’t seen it in years but remembered it being very funny – so we watched it.

It was a fairly funny movie – as long as you don’t think too much about all [...]