Let Us Sex-plain: Should I make a move on my doctor?

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York

Illustration: Assa Ariyoshi

I get it—being single in the city can be tough, and the ways New Yorkers are having sex these days can be surprising. But whatever your dating conundrum might be, I'm here to help. Consider me (Jillian Anthony, Time Out New York's Editor) your personal wingwoman, guiding you through dating and doing it in New York in our weekly "Let Us Sex-plain" column. Check out my answers to all your questions online and in the magazine every Wednesday, and submit your own coitus queries below!

I just moved in with my great boyfriend of one-and-a-half years. His ex left him in the middle of the night, so he always has to hold on to me when he sleeps. But I have insomnia, so I go to sleep at 4am or not at all. At first I would lie down until he went to sleep, and then I’d get up and do chores or watch a movie. When he realized I did this he said it was “not cool.” He thinks that I should see a doctor and take meds, but I function fine. I’ve reassured him I won’t leave in the middle of the night, but this is becoming a big problem. What should I do?

—Sarah, midtown

As long as you’re healthy, this is not your issue—it’s his. He is the one who needs to see a therapist to work through some of his residual issues from his past relationship, and he does not have the right to control when you sleep nor to tell you it’s necessary for you to put medicine in your body. Remind him that while you understand why he’s uncomfortable when you’re not next to him at night, it’s not fair for him to carry something an ex did into your current relationship, and that he needs to do some personal work to move past this if you two are going to continue living together.

My boyfriend is never “rock-hard” when we’re intimate. He went completely soft while I was going down on him the other day.  He’s been with men and women in the past, and I can’t help but wonder if he’s really attracted to me. I know bisexuality is real, and I’m ashamed to feel like this, but I’m questioning whether he’s being honest about his sexuality.

—Emily, midtown

It’s normal that this soft-during-head situation went to your, er, head, but in all likelihood, this is not about you. Each man’s peak-erection strength is different and can change along with physical health or age (erections generally get softer in men age 50 and older). Even if your boyfriend is young and healthy, spontaneous boner loss happens all the time, sometimes for no reason. It’s normal, and generally if you give it a rest for a couple of minutes or try something new, you can pick up where you left off. So try not to make a big deal out of it, and remember your boyfriend probably feels bad enough about it already.

My doctor and I have intense chemistry. He has a girlfriend, and I’ve ended my relationship with my boyfriend. How do I, as the patient, proceed to realize our fantasy? I’m falling so hard for him.

—Liz, Upper West Side

You don’t. He’s taken, but much more importantly, he’s your doctor. It’s unprofessional and unethical for him to get involved with you. And even if you “broke up” with him as a patient, then asked him out, it’s creepy and inappropriate. Let this crush die (how often do you go to the doctor anyway?), or find a new doctor you don’t want to bone.

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Let us sex-plain

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York. Read them all here.

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By: Jillian Anthony

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