1. Why did you take so long to ask me on a second date?
In the beginning of a relationship, you don't want to seem needy or nosy. Certain topics are simply not your business (not yet, anyway). So when Ed waited a few months to call you after the two of you met at a friend's party, you assumed he had been seeing someone else. But you didn't ask about it. You just went to dinner with him. Over time, you got to know one another. You grew closer. Your businesses mingled, and soon you were " RachelAndEd." As in, your friends say, "Who else should we invite? What about RachelAndEd?" Which is when it is finally the time to fill in the blanks, and ask what happened in that months-long gap between the first enchanting conversation by the guacamole bowl and when he actually called to see if you wanted to get dinner. Ed's answer—he wanted to make sure your mutual friend was okay with his asking you out—could surprise you. And make you love him even more. As if that were possible.
2. What beloved dinner do you no longer love?
I was bursting with pride the first time I made my husband dinner and he adored it. The dish was called...drum roll, please...chicken and broccoli on rice. The secret ingredient is—shhh!—soy sauce. Actually, after the chicken and broccoli and rice, soy sauce is the only other ingredient. This meal has taken us through the lean years of graduate school (more rice than chicken), through times when we both worked full time (more chicken than rice), through our childrens picky-eating stages (hold the sauce). And then came the day that so many marriages eventually face. He looked at the chicken and broccoli and rice and couldn't bring himself to eat another bite. I can't blame him. I felt the same way. So don't waste a perfectly good plate of bland food by failing to inquire: What dinner did he once love that he would now prefer never to eat again? And then, you tell him yours. This is a safe place. Get it out. You might just be saving your marriage from drowning...in soy sauce.
3. What do you think of therapy?
When the big things come up—career strife, dying family members, the various typical but nevertheless excruciating heartbreaks of everyone's life—you need to know if talking to someone is an option. Is he up for bringing in outside help for the two of you, or even just the one of you (if that one needs it)? Or will he say, "Psychotherapy? Like for crazy people? Doesn't that cost an awful lot?" Some people find clarity in talking out the big issues with an objective outside party. Others see the whole enterprise as futile, or invasive. It's a conversation to have before you're at that completely-overwhelmed-something's-gotta-give point, when you're still talking about the idea of therapy and not about the personal issue you can hardly think your way through.
Next: The number he's not sharing