Party Game Questions

Author's note: So much has changed since the long-ago days of my youth. People today confront questions that no one could have imagined in the past. I thought it might be interesting put together a few of these questions in the form of a party game for you and your friends. Feel free to offer your thoughts and answers in the comments. Or to add questions of your own.

Party Game Questions

Forget charades – these will really get the conversation started

Peter A. Hempel

Question 1. You are young, single, and aren’t dating anyone, and in fact, it’s been a while since you’ve been with anyone. You meet someone in a bar; they are very attractive and you enjoy talking with them about movies, books, politics, whatever. The attraction is mutual, and you have both had a few drinks.

You are about to head home with them, but then they tell you, as full disclosure, that they used to be the opposite sex. They have fully transitioned, top and bottom, and enjoy sex. Would this be a deal breaker for you?

· Suppose they say, “Since I used to be a man/woman, I know what men/women like. And I don’t have any hangups about anything you might want to do.” Would this make you more interested?

Question 2. You are on a business trip and you meet someone casually and have a random hookup with them. No one you know, no one you work with. You are in a relationship that is not open. When you get home, do you confess to your spouse/partner?

You believe in honesty and communication as essential components of your relationship; on the other hand, if you confess, the other person will be deeply hurt, and even if they choose to “forgive” your transgression, they will unavoidably be confronted with the image of you having sex with some other person – and, of course, regardless of your future behavior, they will find it hard to trust you and will be understandably paranoid. The guilt is on you. Shouldn't it stay there?

·  Does having or not having children affect your answer?

Question 3. Your partner in a non-open relationship, tearfully confesses that they have cheated and have had sex with someone else as a one-time situation.

Does this give you a free pass to have guilt-free sex with someone else as compensation?

Question 4. You meet someone whom you like very much and could easily see getting into a serious relationship with.

Suppose you discover that their body count is more than 3 times (or 4 or 5 or more) your body count. Does that make a difference?

Question 5. You are in a relationship with someone. Both of you have had previous lovers and have been open about that fact. However, at some point, you had a three-way with two members of the opposite sex (or the same sex, in the case of a gay couple). To the best of your knowledge, your partner has never been in a three-way.

Should you tell them about the three-way, knowing that this will leave them with images of you having experiences that a normal two-way sexual situation does not afford?

Question 6. You are browsing in an antique shop and accidentally rub up against a very old oil lamp. Suddenly a genie appears and says, “You do not get to choose your wish, but two weekends from now, you will be magically turned into the opposite sex for 48 hours. You will be very attractive and will have all the appropriate clothing, etc.”

What would you do with your 48 hours? Would you try to have as much sex with as many people as possible to see what sex is like on the other side?

Or would you simply spend 48 hours experiencing a world of male privilege from the opposite point of view?

·  Suppose instead that the genie turned you gay (or, in the case of a gay person, straight) for 48 hours?

Question 7. You are single and unattached. You know someone who is in an open relationship. Through them, you meet their partner, who is quite attractive. At some point, you run into their partner alone and the partner asks you out. You agree, and you end up spending the night together. Everything is consensual and no “rules” have been broken.

When you run into the other person again, what is the appropriate etiquette? Should you mention that, “Oh, by the way, I went out with your partner last weekend. It was very nice.”

Or should you keep it to yourself (and the partner)? In that case, would you be implicitly acting like it was some sort of cheating situation? How would it look if they later found out (possibly through having their partner mention hooking up with you)?

© Peter A. Hempel – 2026

800 words