Recently Maureen O'Connor wrote a lovely piece for New York magazine entitled "The Great First-Date Prenup Experiement." The premise is that before you go out with someone, you could attempt to hash out what happens at the end of your relationship. You hope for the best but plan for the worst. She experimented with an upcoming first date, reaching out to the guy with obvious questions like, "Do we stay friends or ignore each other after the break-up?" and more subtle ones like, "Where do you fall on ex sex?" and "Who gets custody of shared friends?".
While I agree with the author that a sense of realism when entering the dating world is healthy, the dating prenup strikes me as someone setting themselves up for failure. For example, you wouldn't walk into a job interview and immediately ask about the company's severance package, would you? You want to get to know more about the role you'd be taking on, the company culture, the work itself. Only after a handful of interviews, as you get ready to sign your contract, would you even think to contemplate the org's policy around getting laid off.
The same principle applies to dating. You don't walk into a relationship and ask about your exit strategy in an attempt to mitigate any future pain. You take on this other person, knowing that somewhere down the road things might get uncomfortable, and yet commit to enjoying them for who they are. That means you should walk into a first date without a lot of expectations for where things will go. If you two get monogamous down the road and it's important to you to flesh out whether ex sex is on the table, then do it at that time.
To walk into a first date and line up set rules and expectations of any sort spells disaster to me. There are things we could hope for (like that that our date is kind) but I'm talking about things that are more definitive than that. To go to a different extreme, while I appreciate any woman who knows what she's looking for in the dating world, I would fault her for leaning over the table on the first date and whispering, "You know what I really want? To be married in a year."
In prepping for marriage or a break-up you are cutting out room for other possibilities. Maybe at the end of the first date you realize the two of you are better off as friends. A guy who has gone through a break-up prenup or a "where is this going" discussion is not likely to stick around for that friendship, as it sounds like you're an intense friend to have, and he's already let you down by choosing an alternate path. Or maybe you two have great sexual chemistry but you realize he's not the type you want to end up with long-term. Having a dating prenup or a set plan for marriage is going to eliminate that potentially fun exploration as well.
It's natural to want to mitigate pain when entering into relationships. We've all been hurt before, so of course we want to try to plan to avoid that visceral feeling. Relationships are rollercoasters and it's not uncommon to want to avoid extreme highs and lows; most of us want a nice stable ride. The idea that we can set contracts to get us that stability might be the most unrealistic expectation of all. When you go out with someone it could end wonderfully or horribly and no set agreement at the beginning of the date is going to change that. Rip up the prenup and jump on the rollercoaster. It's more fun if you relax and just go with the ride.