When Cathy, 25, moved to Manhattan after college, she cast her net in the sea of eligible New Yorkers by filling out online dating profiles. One question on OKCupid stuck out to her, symbolizing the mismatch she’s felt with single guys:

Say you’ve started seeing someone you really like. As far as you’re concerned, how long will it take before you have sex?

  • 1-2 dates
  • 3-5 dates
  • 6 or more dates
  • Only after the wedding
Screenshot from OkCupid Questionnaire
How Long Should You Wait to Have Sex?

She chose six or more, with the emphasis on ‘more.’ Her matches chose 3-5, in her opinion, “for the sake of not sounding like a douchebag.”“This is always a huge stress for me,” she says. “I don’t think I’ve ever really gotten it right. I always feel a pressure to give in sooner than I want to.”

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Many women struggle to decide when to have sex with a new partner, especially in the age of the digital date when the person you’re seeing may be a perfect stranger. Casual sex is more common today and women wait longer to marry, but there are still plenty of stereotypes about women who give in “too soon” and women who “won’t give it up,” leading many women to feel caught in a web of conflicting pressures.To navigate that mess well, stay true to your emotional and physical needs.

“If you make your decisions based on someone else or how you hope they’ll react, that leads to a lot of disappointment,” says Lena Chen, 24, a self-described “reluctant sexpert” best known for authoring the blog “Sex and the Ivy” while she was an undergrad at Harvard. “Your sexual decisions should be based on what’s right for you and your body.

“When YouBeauty Self-Image Expert Heather Quinlan, LCSW, counsels women about this decision, she encourages them to focus on the choice that’s right for them. “It’s not really a question of right or wrong,” she says. “It’s about, how can we get a healthy outcome?” That answer is different for everyone.

Each of us decides when to have sex in two phases, explains Quinlan. First, you start with a hypothetical, like “If I meet someone new, I want to wait until we’re exclusive before sex.” You’ll consider questions like, what does my religion or my culture teach? What do my friends and family say? Do we need to be in a relationship? Does he or she need STD testing first? You’ll come to a seemingly logical, perfectly planned out time frame.

Then, as anyone who’s been there will know, real life will botch the best-laid plans.Quinlan points out that the circumstances—“who is this particular person?”—matter most. Attraction, relationship status, physical or emotional risk, and emotional availability are just a few of the many factors that suddenly come into play when a real prospect enters the picture.

QUIZ: Are You Sexually Satisfied?

Sex researchers David Buss and Cindy Meston have found that there are 237 reasons why women choose to have sex, ranging from love to pleasure, duty to curiosity, pleasing a partner to seeking an ego boost. Especially among young women, many in their study chose to have sex for the experience or adventure, even the conquest.

One 27-year-old graduate student in Boston, MA has always planned to wait three months (“the amount of time it seems like it would take to get to know someone seeing them once a week”)—but so far, that plan has never worked out. Reasons like physical urges, convenience, and alcohol have always gotten in the way. “This issue may be one of the reasons why I hate dating,” she says. “The protocol is so unknown and it feels weird to talk about it.”No matter how uncomfortable, talking openly about sex can help both of you. “Sexual communication is important for compatibility,” says Chen. “It’s fine to put it on the table. The assumption is that women over-obsess about this while guys don’t care, but that’s not true. This is a subject that impacts them as well and they also feel insecure about how you view them.”

YouBeauty Reader Comments

“I don’t think there is an ideal number of dates or a length of time to wait. I think it’s more a matter of your self-esteem and emotional control.”– ladyamyt, age 31 “I wait until we are both not seeing other people and have both been tested for STIs. It helps to make sure I stay healthy – both physically and emotionally.”– BeautifulDC, age 35

Ultimately, knowing what you want and need is a matter of self-awareness. Taking an honest look at your own limits and desires requires “a lot of trial and error,” says Chen. “Women are taught to be independent nowadays and not need a man, so there’s this assumption that sex should just be easy, we shouldn’t care. It’s not weakness to acknowledge that sometimes you feel closer to someone after sex, or to realize there are things that make you doubt yourself and make you feel insecure. Working through the insecurity helps you gain self-awareness.”

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For a 26-year-old publicist in New York City, her insecurities helped her clarify who she wanted to date. Reflecting on her less serious sexcapades, she recalls, “While there are a few flings I definitely don’t regret, the majority of them ended up not feeling that great in the end. It probably was not really a matter of waiting or not waiting—they were just the wrong people.

”She’s waited “anywhere from two hours to six weeks” and half-jokingly believes in waiting “long enough to learn their last name, or even their first name.” But when she wanted something more, she put the brakes on. With her now-fiancé, she waited six weeks and found that “sleeping together solidified the bond we’d already formed.”

For many women, how long they wait comes down to what they want out of the relationship.“The amount of time I wait to have sex is very dependent on the situation,” says one 26-year-old grant writer in New York City.

“If I want to commit some real time to someone, I take the sexual relationship much more seriously and really demand that waiting period of and for myself.” But when it’s a casual attraction, “timing goes out the window and I just go with the flow.” On the flip side, Chen points out that she slept with her boyfriend of four years on the first date. They’re still going strong today, highlighting that there are no cut-and-dry rules.

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The better you know yourself, the better you can make these choices. But allow yourself some mistakes. “You can be as sexually progressive as you like, but when confronted with the actual situation, you might really feel like you made a mistake,” says Chen. “It’s okay to admit that.” The trick is to learn and move on so you can have better sex next time.