Vexation #2: Out of the Past.
I got an email a couple weeks back from someone asking advice (I get this a lot because of my job) because her 32 year old fiancée and boyfriend of three years has just revealed (at her bequest) the answer to the question "Will I be your first?" and now she is distraught because of his answer. Ay, there's the rub! My problem isn't so much the answer (though that can certainly be problematic!), but the fact that the question was ever asked. What was her purpose in asking the question? She had nothing to gain by any answer he could give.

If he says "No, you won't be my first," she's obviously going to have to deal with all the baggage that comes with that knowing this sorta thing: does he still think of her like that? will he compare me to her? will I be as good as her? This answer will also cause her to doubt her value to her future husband: am I special to him? am I just another piece of meat?

If he says "Yes, you'll be my first," but lies to keep the relationship peaceful, they run the risk of the truth being revealed at a later date. And that'll be worse than if he told her in the first place.

And then if he say "Yes, you'll be my first," and is being honest, what has she gained? Some phantom comfort that is only good so long as she trusts him?

Better I think to assume an answer either way, resolve yourself to it, and never ask the question. That way, you'll have already dealt with what you wish to believe before your relationship gets serious. It may be lying to yourself, but I think it's in your best interest. Some of you may think me an evil bastard (that isn't still a bad word is it?) for this, but I have seen two good relationships of acquaintances crash and burn because one partner couldn't get over the fact that he/she wasn't the other's first intimate. I saw another (a married couple) wherein the relationship didn't die, but it seems forever tainted by a certain sadness because though the fact of the previous encounter was forgiven, it could never be forgotten in fact, after a while, it seemed everything would remind this lady of her husband's "youthful indiscretion" that occurred long before he ever met her.

My advice? Before you ask a question of such import and influence, ask yourself two questions. What do I hope to learn from this? Why does it matter? The first question will probe your motivation for the query; usually, it's asked from a certain insecurity about the strength of a partner's love and if you can't trust your partner's love enough to care nothing for past foibles and sins, you don't trust that partner enough to deserve answer to such an intimate question. The second question will demonstrate that if such information can truly affect the way you love an otherwise entirely lovable person, you, again, have no right to ask such a question for you don't yet love your partner for a true love is imperishable and unmerited.

I guess that's it for today's venting, but as a final note, I thought I should mention that an important question (in this day and epoch) and one that can be asked without fear of misjudgment is "Are you a health risk to me?" This is slightly different, because it makes no judgment upon a potential love interest's current moral state, but simply asks an important mortal consequence.

p.s. I know this raises the question of honesty in relationships, but I'll have to deal with that another time