Your Questions Answered: When To Call It Quits

How many times do you try to make a relationship work before calling it quits?

That’s a great question. I have a theory, if it’s more than two times you probably should end the relationship. When you’re in a serious relationship and you break up and get back together and break up and get back together, I don’t believe that works. I believe that’s a sign that it doesn’t work. If you’re asking to call it quits, you should probably call it quits. Because what happens is, people call and write in asking this and I think that when you break up with someone, and women do this often, we tend to glorify the person after we break up with them. We miss them. We think of all the good things and think, ‘Oh, maybe it’s a good time to get back together.’ But it’s not! Usually, because we’re forgetting all the bad stuff, we get relationship amnesia. You get back together and the same stuff starts to happen. Unless the issues have been worked out and you BOTH worked on those issues, don’t get back together just because you miss them.

 

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“His penis is too big!”

his penis is too big Dear Emily,

My boyfriends penis is too big. I’m 22 and I recently started seeing a guy who has a huge beautiful penis like I’ve never experienced before. This should never be a problem right? Wrong…

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How to Masturbate

how to masturbateDear Emily,

I never learned how to masturbate. It’s really embarrassing. There is no amount of touching myself that will turn me on. I have no problems with a partner stimulating me but when it comes to “special alone time” I’m SOL (shit out of luck). Now I’m in a long-distance relationship and I’m dying without the sex. I want to try a vibrator but I don’t know what kind of stimulation I like because I don’t know how to masturbate. I don’t even know if a vibrator will help. What advice do you have for this situation?

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how many is too many sexual partners?

sexual partners Dear Emily,

How many is too many sexual partners? I’m recently divorced, single, and quite frankly torn with my newfound emotional and sexual freedom.  

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“My Wife Cheated On Me”

my wife cheated on me Dear Emily,

My wife cheated on me. We have a one-year-old little girl and were living happily together. A few weeks ago, I got home from work, and went to log onto the computer we share, and saw a message pop up from some guy. I got to reading their conversation; turns out they had sex while I was at work.

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How do I approach women?

approach women Dear Emily,

How do I approach women? Growing up in SF during the seventies was not great for a men’s sense of masculine self, hearing what “pigs” men are. I choke all the time, even when I know a woman is into me…

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Get What You Want

When dating someone new who you are having sex with how do you bring up the topic of what you like or don’t like while having sex with them (hopefully without hurting the other person’s feelings)? How to do you get what you want?

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Why does she feel objectified?

Dear Emily,

My girlfriend says that in the middle of having sex she starts to feel objectified.  What do you suggest?

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Do vibrators desensitize?

Dear Emily,

My girlfriend needs to use a vibrator to get off, even when she is on top. And oral just didn’t get her there. Is it possible that she’s too used to the vibrator and my manual touch just won’t do it?

Thanks!

Sam

 

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Ask Emily- “How do we find someone for a threesome?”

Dear Emily,

Thank you so much for all of the hard work you put into the show! I listen religiously on my Stitcher app, which is ironic because it’s pretty much the only thing I’m religious about.

Anyway, my question is in regard to “finding a third”. I, a 23-year-old bi woman, and my boyfriend, a 25-year-old straight man, would like to spice things up a bit…

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