Posts by Diana
Pillow Talk with Diana: “I’m Shy About Getting On Top!”
Q: My boyfriend wants me to get on top during sex, and I want to, but I feel too self-conscious about my body! I just feel like like I’ll be on display, with all of my flaws in his face. Any words of wisdom?
A: You will be on display–and your boyfriend will be loving every minute of it. Part of the reason the girl on top position is often requested by guys is because it’s hot! And not just …
Pillow Talk with Diana: “I’ve Been Faking!”
Q: I’ve been with my boyfriend for a year, and I’ve been faking it about three-fourths of the times we have sex (the other fourth of the time is genuinely great!). I started doing it because I didn’t want to hurt his feelings and because he really cares about my satisfaction, but I’m tired of faking, and now I don’t want to hurt his feelings by confessing about the past year. What should I do?
A: I’m sure many people …
Pillow Talk with Diana: Should I Stock Up on Plan B?
Q:What exactly is “Plan B”, that abortion pill, and should I really stock up now in case I need it later?
A: Ladies, listen up: Plan B is NOT the abortion pill. Not by any stretch of the imagination.
So what is it if it’s not the abortion pill? Basically, Plan B what it sounds like — it’s your backup plan, meant to be taken up to 72 hours after unprotected sex or contraceptive failure, to prevent pregnancy. In fact, …
Pillow Talk with Diana: Should I Date an Older Guy?
Q: Is it taboo to date a guy 6 years older in college?
A: I honestly laughed out loud when I saw this question in my inbox. As anyone who knows me can tell you, I have a soft spot for the older men. When I was 19, I found myself newly single after a two-year relationship. After about a week of crying in bed and eating ice cream, I decided it was time to date–and I had eyes only …
Pillow Talk with Diana: Am I Bi?
Q: I’ve had boyfriend my entire life, but I can’t help feeling attracted to some of my straight girl friends. Am I bi?
A: My instinct is to answer your question with “Maybe. Who cares?” and leave it at that, but I’ll try to do my job and actually advise. That said, I can’t tell you whether or not you’re bi. I think it’s possible that you’re crushing on your female friends because it’s a safe way to explore same-sex …
Pillow Talk with Diana: Chlamydia, Herpes, and HPV, Oh My!
Q: I gave head to a guy I met when I was studying abroad, and now I’m worried about STDs. We didn’t use a condom, but he didn’t orgasm. Should I still get tested?
A: Don’t get yourself too worked up over it, but yes, you should get tested. Really, you should get tested after every new sexual partner (yes, oral sex counts). I’ll preface this by saying that I’m not a doctor–which is especially why you should see one–but …
Pillow Talk with Diana: Sex on the Beach
Q: I want to try having sex on the beach this summer. What should I keep in mind?
A: Sex on the beach. It’s the ultimate cliche of sexual fantasies for hopeless romantics everywhere, usually triggered by a movie scene complete with soft lighting and background music. For me, it was Chris Isaak that did it. Specifically, the sexy black-and-white video for his song, “Wicked Game,” featuring soft sand, crashing waves, and leggy supermodel Helena Christensen.
In reality, beach sex …















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