Good & Healthy Relationship Advice & Tips

Unless you’re completely clueless, you probably have a pretty good sense of what not to ask when you're on a first date. (Why are you single? Do you want to have kids some day? How much money do you make?)

But on the flip side, knowing the things you should bring up is equally important. According to psychologist Diana Kirschner, Ph.D., the CEO ofLoveIn90Days.com, the questions here can reveal whether you’re the right match and help you bond in record time.

How so? They all possess the power to transform polite-but-blah chitchat into a fascinating discussion that gets at the heart of who you really are—and that has multiple payoffs for you.

For one thing, you’ll enjoy yourself more if you’re both opening up, rather than sticking to the typical mind-numbing first-date script. And asking these questions will also help you hone in on whether you’re wasting your time with someone who lacks long-term potential (assuming that’s what you’re looking for—if not, by all means indulge in a fun fling!).

It also makes your date more likely to fall for you. “Most of us just skim the surface with a new person,” says Kirschner. “As a result, you can come across as fake and empty.” Delving into deeper discussions than the freakishly warm weather or how the Patriots have been doing will get you authentically excited—and thus make you seem intriguing.

Finally, the more real you both are, the more connected you’ll become. So instead of ending the evening feeling like semi-strangers, you’ll have the sense that you actually get each other.

One heads up before we get started: Although these questions are worded in a strategic way so they doesn’t seem like you’re prying, they arepersonal—it’s best to pepper them in during the middle of the date, once you’ve broken the ice, rather than right off the bat. “Be sure to ask them in a light, fun manner, with a playful tone of voice,” says Kirschner.

Got it? Good. Read on, and prepare to transform your next rendezvous.

1. Do You Like Adventure?

Not only is this question a jumping-off point to talk about cool trips and crazy experiences you’ve each had (lively conversation fodder in itself), but his response also reveals how likely he is to be marriage material. Kirschner says one of the biggest markers of compatibility for a couple is your threshold for spontaneity. “A planner and a thrill-seeker will generally have a hard time making it work,” she says. “Ideally, you want a partner with a similar level of adventurousness.”

So if you’re the type to head on a last-minute getaway and he prefers to prep for a trip ages in advance, you may not click as naturally as you would with someone who shares your taste for the unexpected.

2. What in Your Life Would You Say You Feel Most Grateful For?

"This question can tell you a lot about his value system and whether it’s in sync with yours,” says Kirschner. Case in point: The dude who replies that he’s thankful for having an amazing group of friends who are always there for him is very different from the one who says he’s glad he snagged a big promotion at his law firm.

3. What Was the Best and Worst Part of Your Childhood?

The trick is to tease apart a guy’s past in a way that doesn’t feel nosy—so use a casual tone, and only ask him after sharing something about your own upbringing. “Learning about how he grew up will clue you into his earliest template for love relationships,” says Kirschner. “If a person is from a difficult background, that often indicates there is trouble coming down the pike.” We’re not saying it’s an automatic deal-breaker if his family life was less than ideal, but consider it a warning that you may have to deal with some issues in the future. 

4. If You Could Have Anything You Wanted, What Would Your Dream Life Look Like?

You want to make sure your visions for the future sync up; here’s how to get at that in a way that doesn’t feel loaded. Is he a free spirit or career-driven? Family-oriented or a bachelor for the long haul? All key things to know.