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Let Us Sex-plain: What does “dating” even mean?

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 go on dates with guys who are nice, cute, funny and sweet, but I don’t feel about them the way that I do about guys with whom I feel instant chemistry. My friend says I should give these “nice” guys a chance on a few dates instead of ending things. What do you think?

Jenna, Queens

Sexual chemistry is great, but that alone does not a great relationship make. A good reason to go out with someone two to six times before you make up your mind about them is to get away from your “type” and expand your horizons. Maybe your type is a certain height, hair color or charismatic personality. And maybe that type tends to screw you over. Tap into and push past any part of you that’s attracted to jerks, and give men who don’t fit your archetype (which is mostly in our heads and has little bearing on how a real-life relationship would work out) a chance.

I recently turned 40 and got divorced. Dating again has been confusing, to say the least. It seems that women either want a one-night stand or they want to get married after two dates. Can you shed some light on what “dating” today means?

Alphonse, Upper West Side

Honestly, Alphonse, who really knows? Dating means something different to each damn one of us. Each complicated, brooding being has an image in their head of what they want, and it’s extremely rare for that image to match yours and lead to a happy relationship. The good news is, love happens all the time! It just takes patience and a lot of bad-to-average dates to get there. Be extra kind to yourself during this time of transition, focus on your own passions, and know that a new partnership is in your future.

After matching on online dating apps, I’ve noticed that women have a tendency to start the conversation with “Hi” or “How are you?” But I’ve seen surveys results claiming that women say a guy shouldn’t start a conversation with just “Hi.” Why do women do this so regularly?

David, Bushwick

You’re missing the obvious. Both women and men start conversations in this obnoxious way, and both sexes hate it. I attribute a lot of this behavior to laziness and disenchantment with online dating. There are so many people to talk to, and it takes time and thought to message each one of them with something interesting. Instead, a fishing “Hi!” means you’ve done your bare-minimum duty (apps have shown that you’ll receive far fewer responses with a “Hi” than with a more personal message). And people (especially men, who get more nonresponses than women) get sick of sending thoughtful messages into the void. Both reasons make sense, but if you want online dating to work for you, you have to put intention into it. If you feel yourself getting frustrated, take a break and work up the courage to talk to someone IRL.

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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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