The Big Questions
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The Big Questions

Learn the right questions to ask at every stage of a relationship.

Questions, Questions

When it comes to relationships, psychologist Dr. Judith Sills says that there are two kinds of people: askers and non-askers. "Askers ask way too early -- on date three they'll ask 'What do you think about children and what religion should they be raised in?'" Non-askers ask way too late, if at all, so after the wedding they'll say 'What do you mean you were married before?'" says Sills, author of the forthcoming If The Horse is Dead, Get Off (Viking, 2004).

Small queries can lead to big answers when looking for a life mate -- here's a brief guide to what to ask, and when.

Part One: You've Just Met

You're at a party, on a blind date, or just hanging out with friends. So far you like what you see. He's attractive, well groomed, and doesn't appear to have any major substance addictions. Get to know him a little better by asking:

1. What did you do today? When asked on a weeknight, this is a subtle way of finding out if your potential beau is gainfully employed. On a weekend, this will tell you if your interests are compatible -- "Got up at 7 to run" or "Slept until noon" will hold various levels of appeal or disgust, depending on your own point of view.

2. What do you love about your job? We've all experienced that horrible awkward pause after you ask a man what he does and he informs you that he sells packaging materials. But what he does is far less important than why he does it. So give him a chance to tell you why being an insurance actuary is actually fascinating work, or that he loves nothing but the money he makes. Either way, the answer will be revealing.


3. What CDs are in your stereo right now? If you ask him what kind of music he likes, you'll probably learn more about what kind of music he thinks sounds impressive at cocktail parties than what he sings in the shower. So put him on the spot and let him confess that he listened to his old Flock of Seagulls album this morning. You may find that you have the same guilty pleasures.

4. What brought you to New York/Seattle/Boise? The reasons that people pick up and move to new places -- "I fell in love," "I wanted to pursue my dream of being a landscape architect," "My college pal needed a roommate" -- reveal a lot about a person's spirit. And if they've lived the same place their entire life? Well, that tells you a lot too.

5. So did you see that story about the guy who was in a coma for 19 years? By asking about a compelling news story, you'll get a good sense of whether your interests meld. You'll also keep your first encounter from sounding too much like a job interview.


Part Two: Going to the Next Level

Life with your new man has been blissful. He's been a perfect gentleman. Picks you up at the door to go to concerts, movies, romantic dinners. The physical attraction has been strong, so much so that you're hoping he won't be quite so gentlemanly at the end of the evening. But are you ready for serious physical intimacy? Ask him:

1. When do you think is the right time to sleep with someone? This question should be asked in a relatively low-key environment -- when you're walking in the park, getting an ice-cream cone, fishing. Not when he's fumbling with your bra strap. The idea here is to get his general philosophy, without necessarily commenting on your relationship.


2. Are you seeing anyone else? It might seem unfathomable that the man you've felt so connected with all these months could have another girlfriend, but he may have an entirely different interpretation of your relationship. So while you may not like the answer, it's better to learn this before you ask him to spend the night.

3. Do you worry about STDs? Asking a guy if he's been tested for sexually transmitted diseases is about as romantic as asking him to pee in a cup. This is never an easy topic, so start by asking a more philosophical question. "The bottom line is you have to have the safe-sex talk, and you have to come to an agreement that you're both comfortable with, whether that means wearing condoms, getting tested, or both," says Sills.

4. Are you sure you're ready for this? This will let him know that you take the relationship seriously, that there indeed is something one needs to be "ready" for.

5. What are my parents' first names? Okay, you don't literally ask this question. But if he's viewing this as the next step in building a committed relationship, then he should already know some basic stuff about you. "You really want to be at the point where the relationship is stable enough so that you don't have to ask. Is he part of your life? Has he met your friends and family? Or is he just someone you've been on six dates with? Behavior answers this question more than a conversation," says Sills.

Part Three: Shacking Up

The way you see it, you're together all the time anyway. He keeps a dopp kit in your medicine cabinet and you have a change of work clothes in his closet. But before you start playing house, have a frank discussion about a few issues:

1. What's our commitment level? It's not that you have to decide that living together equals engagement, or even pre-engagement. But you both need to know where the other one stands. If one of you assumes that you'll be getting engaged in a year and the other thinks you're just saving on rent, then there's sure to be trouble ahead.

2. What are your concerns about our compatibility? Will it drive him crazy that you leave dirty dishes in the sink overnight? Can you deal with the fact that he needs the television on 24-7? "You're sharing more time, more space, more money, so it's natural that things will come up," says Sills. The more you discuss your idiosyncrasies beforehand, the easier it will be.


3. What are your expectations regarding togetherness? Will he leave you home every night watching Sex in the City while he plays pool with the guys? Or will he be angry when he discovers you work until 9 p.m. most evenings? If one of you expects to be joined at the hip, while the other plans on maintaining a separate life, then there'll be a lot of tension in your household if you don't sort things out now.

4. How will we pay for stuff? Are you planning on splitting each bill down the middle, or will the person who earns more pay more? And what's your money style -- do you go crazy if bills aren't paid on the 1st of the month, or do you wait until the last minute? "This is a romantic relationship with a powerful economic variable, so you need to have a frank economic discussion because these issues will definitely surface," says Sills.

5. How will we divide the chores? If you're a neat freak and he tends to leave his dirty underwear on the living-room floor, then it's probably not realistic to expect him to keep the place up to your standards. You don't have to divide each job equally down the middle, but you do need to find a system that you both think is fair. Decide where you're willing to compromise, and what you're willing to contribute.

Part Four: Getting Married

Before you start picking out china patterns and interviewing caterers, make sure you've got this stuff squared away:


1. How do you feel about kids? Obviously, this is key. But if you both decide you want children, don't leave it at that. You also need to find out what sacrifices he's willing to make to ensure that these children will be raised, clothed, and fed. Will he be willing to quit his job to raise them? Will he be willing to get a job to support them?

2. Is there anything I need to know about your finances? Just because he wears expensive Italian suits and always dines at 5-star restaurants, doesn't mean he doesn't have financial troubles. In fact, those designer clothes and gourmet meals could well be the reason for his money woes. So before you co-mingle your finances, you need to know if you're marrying thousands of dollars in credit-card debt, in addition to a sharp dresser and a discriminating palate.

3. Where do you want to have the ceremony? Even if he has never mentioned his religion, don't assume that he'll be willing to recite his nuptials at your hometown church, or even City Hall. Weddings often bring out strong feelings of religious or family loyalty, so it's important that you speak respectfully to each other about whether you'll have a religious or civil ceremony, whose hometown you'll marry in, and who will be expected to convert.

4. What are your expectations about seeing our families? Is your idea of family values seeing your relatives for a couple of days at Christmastime, or having dinner with them every Sunday?

5. What are your most significant life experiences? If he once was a member of Gamblers Anonymous, has already been married, or if his dad was an alcoholic, then you should know this before you tie the knot. "Marriage is full disclosure. You don't need to tell him how many people you've slept with, but if he thinks that you've never slept with anyone, then that's lying," says Sills. So even if you think you know your partner down to his toenails, make sure you have this discussion. The fewer surprises the better. Says Sills, "The closer you are, the less romantic the wedding, and the more solid the marriage."