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Let Us Sex-plain: My date got scared off by my big dick

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

Illustration: Alex Citrin

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!

My boyfriend of a year and a half has a girl best friend. Most of the time I’m supportive of their friendship, but sometimes I can’t help but feel annoyed by it. It feels like the only difference between his relationship with me and his relationship with her is that we have sex. Am I wrong for feeling bothered by this?

—Marisa, Lower East Side

Yes. If this friend were a man, would the close friendship bother you? I’m guessing the answer is no, meaning you’re dealing with some misguided jealousy. Think deeper about why you’re feeling this way and realize that if this woman is truly a good friend to your boyfriend, you should be overjoyed she’s in his life.

After three great dates with a girl, she invited me up to her place. Things were getting physical, but when I took off my pants she freaked out, saying that my penis was way too big. I assured her I’d take my time and we could start with other stuff, but she kept saying there was no way. After that very awkward interaction, I got dressed and left. Two days later she texted me saying she wants to try again. The way she handled things felt childish, but our dates were great. Should I try again?

—Andy, Bedford-Stuyvesant

Congratulations on your big dick! While I can understand this girl’s trepidation, it was unkind and immature of her to make your penis out to be so freakish; it’s simply not nice for someone to treat any body part as an anomaly, especially a part we’re all so sensitive about to begin with. If you really like her, go ahead and see her again, but do so at your own risk: She seems like an unaware person at best and someone with little concern for others’ feelings at worst. And make sure she’s not just using you for the story.

I’ve been dating my best friend of seven years for seven months. He rejects sex with me so often that I’ve stopped asking, and he’s constantly on his phone or playing PS4. I feel alone and abandoned when he’s lying right next to me. He’s good with opening doors and forehead kisses, but I need more. What should I do?

—Shy, East Village

Opening doors and forehead kisses?!? If that’s your threshold for what it means to be a good partner, your expectations need to go way up. This man may be a good friend to you, but he’s anything but a great boyfriend. You know you’re unhappy, and you know you need more than what this person is offering to you. Don’t wait around for him to change or expect that he will. Break off the relationship now, and be sure to give yourself and him some time and distance before attempting to be friends again.

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Read previous weeks’ sex columns

Let us sex-plain

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

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By: Jillian Anthony

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