Tell Me About It: Key questions she must ask fiance

Question:

My fiance and I are both divorced parents of elementary-age children. We have been dating about nine months, so in many ways we're still learning about each other. I know he dated quite a bit after his divorce and before he met me. He even dated a casual friend of mine, before I knew him.

I find myself wondering about his sexual escapades. This time period was brief for him, but I get the impression he sowed a lot of wild oats. He said the friend of mine he dated just wanted a "friend with benefits."

I recently stumbled across an assortment of condoms and oils (that we have never used) in the nightstands that flank his bed, with cards and photos from other women. I wonder why he would still hang on to such things and especially within easy access - if I could find them, so could his young children.

I don't want to ask him about this because it's none of my business and I know I won't like his answers. But why would he have asked me to marry him if he's holding on to such "mementos"?

Answer: You know you won't like the answers, so . . . you're going to put a bag over your head and make him your kids' stepdaddy?

What he leaves in child-accessible drawers, and why, is thoroughly your business. How he views casual (and noncasual) sex is your business. How well he tended to his health in his oat-sowing phase is particularly your business.

You have the right to know who he is, and you're overdue to assert your interests here.

Far more important: Your failure to act in your own interests has the potential to hurt your kids.

First, if you're too timid to ask basic questions of a man you've agreed to marry, then how will you ever be confident you're making a responsible choice for them?

Second, how can you teach your kids to advocate for themselves if the approach you model is to duck and defer?

Starting a difficult conversation is the hardest part, so, here: "I noticed you've got all this stuff in your nightstands, and my first thought when I saw it was, 'What if his kids looked in there?' "

Listen carefully to what he says, so you're more informed when you raise the topic you absolutely must raise, the possibility that your values differ on sex.

Two adults who are ready to share a life will be able to have this conversation.

If you don't like his answers, though - or if he refuses to answer, or, worse, turns it back on you - and if your first impulse after that is to wonder how you can express your dismay without shaking up the relationship, then I'm going to beg you to put the engagement on hold while you try to get on speaking terms with your own inner voice. And to talk to a skilled therapist about your tendency to be passive when leadership is what the situation demands.