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Should I ask if he's dating others?

To keep the conversation from starting off with an accusatory tone, ask if he or she is dating other people. "You can say that casually," says Aaron. And then, "if they say they're seeing other people it's totally appropriate to ask if that means they're sleeping with other people."

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In every relationship, there comes a point where you have to say those five little words: Are you seeing other people?

"That conversation usually comes up at about the one- or two-month mark," says, Michael Aaron, Ph.D., a New York City-based sex therapist. "At this point, people are starting to develop feelings for each other and they want to know where it’s going." While it's a totally normal conversation to have, being the one to bring it up can feel nerve-wracking as heck. "People have a lot of anxiety about it," Aaron says. "But you need to feel confident that you have every right to ask that question." So how do you have the talk without losing your cool? We asked Aaron for his tips on how to ask your new guy or girl if they're sleeping with other people. The best way to avoid an awkward (and potentially heartbreaking) conversation, is to be direct about what you want. "At the very beginning, you want to be clear with the person you’re going on dates with about what kind of relationship you’re looking for," he says. That means, don't try to play it cool and say you're only looking for a casual hookup if you really want a relationship. You'll only be setting yourself up for a trickier talk down the road. (Spice up your sex life with this organic lube from the Women's Health Boutique.) Although being upfront about what you're looking for can be a good tactic, be aware that asking a new guy or girl for a commitment too soon may feel like an interrogation, says Aaron. "It might feel presumptive or like you’re pressuring someone." So when does it stop being weird to bring it up? Once you've been hanging out with someone regularly (which Aaron defines as two to three times a week) for a couple months, that's usually the appropriate time to ask. "When it gets to that level of frequency, it’s a fair question because you’re taking up a lot of each other’s time." If you want to keep the conversation out of panic-induced, committment-a-phobe territory, keep it casual with direct, simple questions, says Aaron. "I wouldn’t necessarily start with 'Are you having sex with other people?'" Coming right out of the gate with a charged question can put the person you're dating on the defensive. To keep the conversation from starting off with an accusatory tone, ask if he or she is dating other people. "You can say that casually," says Aaron. And then, "if they say they’re seeing other people it’s totally appropriate to ask if that means they’re sleeping with other people." We asked guys whether you should tell them you're seeing someone else. See what they had to say:

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According to Aaron, it's best to focus on the present, rather than have a potentially freaky conversation about the future. "A question like 'Where do you see us going?' is a future-oriented question," he says. Those kind of questions take things to a serious place, which can make the conversation feel very intimidating if you're both trying to gauge if you're interested in a serious relationship. "I think people are much better off asking present-oriented questions like, "Are you dating other people at the moment?'" he says. "You’re just asking about the here and now. If someone is uncomfortable with present-oriented questions, I think that’s a red flag." Avoiding the question is also a big red flag. Even if the person you've been seeing doesn't give you the answer you want, they should still offer up an answer. "You want a clear and direct response. If you’re not getting one, that to me feels shady," says Aaron. As scary as bringing up a potentially awkward conversation can be, it's scarier to not be looking out for your own body. "I hear it all the time that people aren’t using condoms like they should, but that’s playing with your health," Aaron says. At the end of the day, you need the facts about the person you're seeing so that you can make empowered decisions about your sex life. And that is nothing to be embarrassed about.

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