I recall an experience that happened between Daisy and I. Daisy was attending a multi day festival with friends and I asked her who she would be sleeping with, my question was literal and her response was speculation, which of course I interpreted as literal since that was my frame of mind.
After she returned from the festival she revealed that she slept with a different person than she originally told me it would be. A person I having some jealousy issues with no less. The emotions I was feeling about that person in combination with the conversation we had before she left for the festival left me feeling deceived. And in that moment, to be completely honest I could not shake that feeling of deception.
What I learned from that experience is that whenever you are asking someone to speculate you are setting yourself up to feel deceived. Some speculations can be entertaining conversations, because whether the speculation turns out to be accurate or not is inconsequential. I think speculation about emotionally charged topics on the other hand is probably not healthy for most relationships. Ultimately, I decided that speculation about certain topics was not appropriate for my intimate relationships.
I personally have the approach of thinking, " I said I am doing 'X' so I will not allow 'Y'.
I assume your wife knows this about you. So when you ask her if she is prepared for sex what you are really asking her to do is predict the future. Because if she says "no, I am not prepared" and then finds out during the date that she is prepared for sex in that moment, she risks making you feel deceived because you are going to project your own mental hardwiring onto the situation.
The spouse also may be reluctant to say "Yes, I am prepared" for personal reasons.... What if she is not 100% certain? Or maybe she is prepared and excited but doesn't want to jinx it. Or maybe she has been slut shamed in her past and that trauma results in her reluctance to admit that she is prepared to have sex with someone on a first date...
These conversations might seem simple to you but there is a lot to unpack here. In my opinion this sort of speculation is just asking for confusion, hurt feelings, and emotionally charged conversations. I think it is logical to assume that sex can happen at any time and especially on a date, it goes without saying...
As far as preparation for sex? If you have a safe sex agreement than I think the spouse agreeing to have condoms available when she goes out is reasonable. If you do not have a safe sex agreement knowing if protected/unprotected sex happened before you are intimate with your spouse again is reasonable.
Well, there are more parts at play in terms of our history. I flat out had a mental and emotional breakdown crying for almost 20 hrs because I felt and still feel that she and have disproportionate invest in quality time with each other.
This sounds like hell... And she isn't even fucking anyone yet. I honestly think you should re-evaluate your participation in this relationship. Especially if you find things getting worse and not better after dating.