Despite what movies tell us, there’s no hard and fast rule about when you should have sex with your new guy for the first time. Maybe it’s five minutes after you meet him, or maybe it’s after marriage—no judgment!
But no matter how long you wait, there are some questions you need to ask both your partner and yourself before you get in bed. Some are obvious—almost everybody knows to ask about STIs and birth control, and it makes sense to have a conversation about where the relationship is going. But other questions aren’t as straightforward. For example, how do you ask a guy you’ve just met whether he’s an arrogant jerk who’s selfish in bed? Easy: You don’t. But that doesn’t mean you can’t figure it out with a few less direct questions. We talked to the experts, including a former CIA officer, to figure out what answers you need before you get intimate with him—and what the right questions are to see the red flags.
1. Have you been tested?
STIs are serious business, and that means that you can’t gloss over the topic just because it doesn’t match the mood, says human sexuality researcher Dr. Nicole Prause. “Data shows that when people say ‘I’m clean,’ what they really mean is that they haven’t seen any active growths,” Prause says. “And when they say they’ve ‘tested clean,’ they’re usually only talking about HIV. So the sex questions need to get pretty explicit!” The easiest way to make this conversation less awkward is to get tested yourself. “The most common reason people don’t bring up STIs with a potential partner is because they haven’t been tested,” says Dr. Debby Herbenick, author of the book The Coregasm Workout. “They know the question is going to get turned back on them. Get tested yourself, and the conversation will be much easier.” (Related: Sex during UTI?).
2. Are you married?
Even if this is just a casual relationship, you want to know if he’s seeing other women. And you should, says Herbenick, because—jealousy aside—it’s important to know what kind of situation you might be getting yourself into. Most of us assume if a guy is dating he isn’t betrothed, but, well, we’ve all heard the stories. Sure, a married guy probably isn’t going to come right out and admit it, but by asking him directly, you’ll put him on the spot enough that he won’t be able to lie smoothly, either. Ask this question in a joking manner, and then you can use it as a stepping stone to say, “No, but seriously, are you seeing other women?”
3. Do you like your job?
What do you do? Do you enjoy it? What’s a typical workday like? Do you like your coworkers?
Don’t ask him these questions all at once—you’re not interrogating him, after all. But asking four or five specific questions about one topic is an easy way to spot a liar, according to retired CIA covert operations officer B.D. Foley, author of CIA Street Smarts for Women. “In the CIA, we try to have a cover story that will survive three questions,” Foley explains. “After three questions, it becomes difficult to maintain the cover, so we then try to redirect the conversation. This is what a liar will probably do.” You don’t need to catch him in a fabrication to figure out if he’s a liar, just pay attention to whether he starts being evasive when the line of questioning goes too deep. And remember: If he’s lying about something as trivial as his job (even if it’s just to impress you), he’s probably lying about other things too.
4. Nice car! Is that what you use to pick up chicks?
Flattery is everything—when you’re trying to out arrogance, Foley says. Figure out if he has an ego by, ironically, stroking it. “This is called a ‘flattery ploy,'” Foley says. “A normal, humble guy will take compliments graciously, or even be embarrassed. But someone who is arrogant will use your words as a jumping off point to brag about themselves or their exploits.” If he takes every compliment you give him and follows it with a 10-minute speech about how amazing he is, he’s probably not the kind of guy you want to sleep with (read: selfish, and potentially selfish in bed).
5. Are you friends with your ex?
The way he talks about past relationships can be revealing, says New York-based psychologist Dr. Ben Michaelis, author of Your Next Big Thing: Ten Small Steps to Get Moving and Get Happy. “If he’s respectful when talking about an ex-lover, that’s a good sign that he’ll be respectful of you,” he explains. It can be a little awkward to bluntly ask a guy to reveal his relationship history, so lead in to the question with some (inoffensive) info about your past relationships. “At the CIA, we call this ‘give to get,'” Foley says. “When you give some information about yourself, the other person will feel compelled to respond in kind.”
6. Bad hair day, huh?
Safety is important, especially when you’re getting intimate with a new partner. But if you’ve just met him, you probably haven’t had the chance to see his true colors. The most important to suss out is any anger or control issues, both of which can be problematic even if you never plan on seeing him again. To determine whether he’s a regular guy or a possible serial killer, Foley suggests using a “mild provocation” ploy. Here’s how it works: Provoke him by gently teasing him about something he’s clearly proud of, like his new car or his nicely-groomed beard. “People with violent tendencies are often unable to resist a poke like this,” Foley says. “They’ll become irritated or even angry. It’s better to see this behavior come out in a bar, when you’re surrounded by people, than in the bedroom.” Just remember to keep it light. You’re not actually trying to offend him (and some guys are really sensitive about their hair!).
(Related: Tips for healthy combination hair).
7. What are my expectations?
Before you sleep with him, it’s important to ask yourself what you want in both the sexual encounter and the relationship. Strong emotions often come when your expectations are violated, like when you unexpectedly win an award and are ecstatic, or dramatically saddened by an abrupt death, says Prause. Because you tend to romanticize sex before it happens, your expectations are high. That can be problematic if you’re not prepared to deal with the fallout. It doesn’t matter if you’re looking for a one-night stand or a long-term relationship (or something in between), just be honest and realistic about what you expect to happen the morning after (and what scenario you’re okay with), she says.
8. Am I okay never seeing him again?
Sometimes it’s difficult to be honest with yourself about whether you can handle a casual relationship, so Herbenick suggests considering the worst-case scenario. “If your answer is yes, then go for it,” Herbenick says. “But if it’s no, you may want to wait until it is yes, or until you’re both ready for a more serious relationship.” (In the meantime, he’s not the only one with some sex ed homework!