You may see a number of resources with love and sex questions that are claimed to be fun. When dealing with sex in new relationships however, you’ll inevitably come across questions about sexually transmitted diseases, cheating, previous partners and your overall sexual history. These are important dating questions but they are definitely not fun nor are they easy to talk about. However, they are questions that you absolutely must know the answers too. Here is a sample of the types of dating questions you may encounter:

• Do you have any sexually transmitted diseases?
• Have you ever had any curable sexually transmitted infection?
• Have you ever had unprotected sex?
• Have you ever cheated while in a relationship?
• Have you ever had sex with a partner of the same sex?
• Have you ever been forced to have sex?
• Have you ever forced someone to have sex with you?
• Have you experienced any sexually traumatic events?
• Do you have any sexually deviant desires or fantasies?
• Have you been charged or convicted of any sex related offence?
• Do you have any restraining orders for or against you?

These are definitely not the type of dating questions most people want to discuss over dinner let alone during passionate foreplay leading to hot sex. But don’t get me wrong, you need to ask these serious questions and be confident about the answers you’re given. And of course, you need to be informed and truthful about your own situation. However, there are some improvements that could be made to these questions to make them more suited to conversation rather than seeming to be part of an interrogation.

One of the biggest problems I have with the style of question above is that they are all setup for yes/no answers. This doesn’t lead to any meaningful conversation. Simplistic answers provide no insight or clues as to the nature of the experience nor how it affected them personally. In my opinion, yes/no questions seem to be confrontational with somewhat negative overtones. They also tend to inhibit discussion rather than encouraging it. Followup questions make you feel like you’re being grilled. But by rephrasing them, you can set the mood for an engaging exchange of information and ideas. This will give you a much better sense of how a person thinks, feels and behaves – always remember though that what people say and do don’t always match.

• What is the worst sex related experience you’ve had?
• When was the last time you’ve been tested for any sexually transmitted infection?
• How many common types of STD’s can you name and describe?
• What does “safe sex” mean to you?
• What kinds of activities do you consider to be sexually deviant?
• What are your views on fidelity in a relationship?
• How do you feel about homosexual relationships?
• How did you learn about sex?

Once you start the discussion, you’ll find it naturally leads to more revealing questions without making each other feel that you’re probing them.

Before you have sex with a new partner, you’ll definitely want to get the conversation onto STD’s. But before you can jump to this topic, you’ll need to develop trust in the relationship. Most people will not outright lie about this sensitive subject but they also may not be as forth coming as they should unless they feel very comfortable with you. People may leave out important details or even give misleading answers that are truthful on the surface but only hint at the information you need to know. They may also have mistaken beliefs or be misinformed such that their answers are inaccurate or even completely wrong. This means that you will need to have many deep conversations about a lot of subjects to develop a sense of your partner’s openness. You’ll also want to ask the same types of questions in multiple ways to ensure their answers are consistent.

Let’s take a look at a sample sex question: Have you ever had unprotected sex? For people who regularly wear condoms, the initial response might be “No” with little thought or hesitation. However if you ask the question: ‘What does “safe sex” mean to you?’, you may discover that their condom use is restricted to only vaginal sex for contraceptive purposes. Oral sex (both for him and her) or anal sex may not require a condom or dental dam in their opinion. These practices may not coincide with what you believe to be proper safe sex.

For more relationship and dating questions, download 500 Intimate Questions for Couples and get your conversation started. It helps guide you through these not so fun sex questions by mixing them in with others that are more fun.

One caution: when sharing secret thoughts and details with each other, start slow and get more serious as you increase your levels of trust in each other. Keep the questions light hearted and focus on relationship building questions rather than any subtle or implied accusations. Also listen intently to your partner with an open mind – you’re asking dating questions to better understand each other and develop a deeper emotional connection.

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