Crucial Questions to Ask Before Sleeping With Him

Don’t shy away from the hard questions

If you want a chance to have a serious relationship with a guy, there are certain questions that you should ask before you have sex with him.

No matter how tough it is to ask these questions, keep in mind that if you aren't comfortable asking them, why are you willing to get into bed with someone who is basically a stranger?

That is, unless all you want is a casual relationship. So first, ask yourself a few questions, such as what do you want? If you want a shot at a long-term relationship, then there are things you need to know before getting intimate between the sheets.

Crucial Questions to Ask Before Sleeping With Him

Things to ask once it's time to step it up

Many women want to know what to ask a man once she’s decided she is open to intimacy with a man, according to Toni Coleman, psychotherapist and relationship coach.

“She should begin by thinking about what her top concerns might be and how she could broach these with him through discussion and direct questions,” Coleman said.

Some common examples of the important questions that Coleman said women want answers to include:

  • Are you looking for anything more than just a fun sexual experience? After all, if the woman is feeling an interest in more from him, she needs to know his intentions or risk experiencing disappointment/ hurt/regret.
  • Have you had a lot of sexual experiences/partners?
  • Do you have any questions or concerns about my sexual experiences and history?
  • Do you have any history of STD’s that I need to know about?
  • Do you usually use protection and how do you feel about my insisting that we do so, at least at first?
  • If I’m just not ready yet, how do you feel about that? If a guy pushes her in spite of her reservations, it’s unlikely this guy is a keeper.

Challenging communication

Don’t worry if it feels tough to ask such questions. Patricia Johnson and Mark Michaels, co-authors of Designer Relationships, Partners in Passion, Great Sex Made Simple, Tantra for Erotic Empowerment, and The Essence of Tantric Sexuality, said, “It’s not easy to talk about safer sex practices and test results. Even people who are good communicators and experienced sexual adventurers can find it challenging.”

“Almost everyone has bought into the idea that sex should be spontaneous, and talking about protection and test status interferes with that spontaneity,” Johnson and Michaels said. But, that’s not wise, because protection is needed when a partner is new to you.

To introduce the subject, Johnson and Michaels suggested the following: “I really, really like you, and I feel like things are moving in an intimate direction. While I’d love for things to be crazy spontaneous and hot, I want to have a conversation about something kind of serious. I have some hard and fast boundaries around safer sex; I also want to do what I can to make sure that we have as much fun together as possible, so can we talk about a few things?”

Additional questions to ask a new partner

  • Have you ever used IV drugs?
  • Are you having sex with anyone else right now?
  • Are you having sex with anyone else right now?
  • Are we exclusive or casual?
  • How long has it been since you last had sex?
  • When and why did your last relationship end?
  • What do you want out of this encounter?
  • Are you staying the night (or are you invited to spend the night if you're at his place)?

No matter how difficult these questions are to ask in the heat of the moment, it’s essential to ask before you have sex. Weeks down the road, once your heart is committed, it will be even tougher to ask if you’re exclusive and find out you’re not.

And as Tina B. Tessina, (aka “Dr. Romance”) psychotherapist and author of the forthcoming Dr. Romance's Guide to Dating In the Digital Age said, “Hopefully, you'll know a guy you're about to sleep with, at least a little bit. If so, you may know the answer to these questions already. If you have to ask them, you're probably having sex too soon.”

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