Let Us Sex-plain: How do I get my boyfriend to try sex toys with me?

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

Illustration: Marina Esmeraldo

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 went on a date with a guy last year, and although it proved to be a one-night stand, I really enjoyed our conversation—and the sex wasn’t bad, either. A couple of weeks later, I ran into him at a party and drunkenly asked why things didn’t work out, and he said he just wanted to be friends. We work in the same industry, and he’s going to be working in my office for a while soon. Do I call out sick or avoid eye contact?

—Chris, Williamsburg

Neither. Follow my foolproof Rule of the First Strike: In any and all awkward social situations, go right up to the potentially problematic person with a smile on your face, say hello, and make minimal, friendly small talk. This breaks the tension and gets the hard part out of the way, so you can move on to the people around you who actually matter. It automatically makes you the bigger person, and it works every damn time.

How do I get my boyfriend to try toys with me?

—Rita, Brooklyn

Mention that it’s something you’d like to try and gauge his reaction. Some guys take a big ego hit when a partner mentions bringing sex toys into the bedroom because they’re worried their dick isn’t good enough to get the job done. If he’s one of those, remind him that you love your shared sex life but that there’s always room to try new and exciting things. Plus, unlike the male member, toys can hit your clitoris during foreplay or sex, which is the only way about two-thirds of women can come (meaning, sadly, a dick alone is not usually good enough when it comes to the female orgasm). That frees up both of you to try new positions, and lets him focus more on himself rather than taking care of you. (I’m assuming he’s a very generous man, for your sake.) Then go to a store together so you can browse the shelves and see what you both like! There are plenty of toys made for his pleasure, too.

I’ve been dating a guy about 10 years older than me for the past five months. Things have been great, and we are exclusive. His family comes to visit often, but he never invites me anywhere with them. I’m starting to feel like they don’t even know he’s dating someone. It makes me wonder how seriously he is taking our relationship. Am I overreacting?

—Christine, Upper East Side

Five months of dating is not long enough for you to raise too many alarm bells about this. This man is 10 years older than you, so he’s likely dated (and brought home to mom and pop) several partners along the way, which may mean he’s a bit more hesitant this time around. Instead of rushing, continue to get to know each other, and allow him to make his own decision about when and how to introduce you to his family. However, you also deserve the right to feel secure in this relationship, so if you can’t get it off your mind, talk to him about it! The only way you’ll know what he’s thinking is if you ask.

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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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