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Photograph: Alex Citrin

Let Us Sex-plain: How often should I get tested for STDs?

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

Written by
Jillian Anthony

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 recently had sex for the first time with a guy I really like, but we were both drunk, and it was a bit sloppy, and neither of us finished. Usually I enjoy sex more when I know someone better and it’s more intimate. Now I’m afraid we got off on the wrong foot, sexually. How do I let him know I actually want to take things slow without hurting his feelings about the bad sex?
—Alex, West Village

Slow your roll. A first time, especially when under the influence, can be awkward for anyone. Why not just chalk this one up to new-partner jitters and try again rather than overanalyze the situation and make a big deal out of what’s probably nothing? Have sober sex a couple more times, and use your body language to show how you like to be touched. If it’s still awful, that’s when you can start overthinking things. Or just tell this guy you’d like to get to know him more before you sleep together again.

If you have safe sex practices, how often should you be tested for STDs?
—Jenna, Queens

Sex is never completely safe: There’s always a chance you could catch a sexually transmitted infection (STI) or make a baby (if the two of you have those corresponding baby-making parts). So better safe than sorry! If you’re sexually active with more than one partner (especially if you’re a man having sex with men), get checked as often as every three months and at least once a year to make sure you and your partners are clean (to search for free clinics, visit And if you’re in a monogamous relationship, get tested once a year; some STIs can become symptomatic much later (and, let’s be real: Your partner could cheat on you and expose you to STIs).

About a year and a half ago I met an amazing woman through a mutual friend. We’ve built up a pretty cool friendship that I value very much. She’s in a long-distance relationship with a man and seems to teeter back and forth between single and committed. We’ve been spending more and more time together, and I can seriously see myself dating her, but I’m just not willing to make a move knowing it might cause some drama. If I wait, do you think this will hurt my chances in the future?
—Angela, Astoria

You care for this person, so act in her best interest. It’s not your place to step in and break up this relationship. Let her figure it out for herself, and be there for her as a friend (if you truly can; when you have feelings for someone, that’s much easier said than done). If you make a move now, the relationship would start from such a confused and morally questionable place; I fear both of you would just end up hurt. But in the future, if she finds herself single and in a good place (read: not immediately after a breakup), you should tell her how you feel and see how she reacts.

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Read previous weeks’ sex columns

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