Questions You Should and Should Not Ask Your Date

Dating really is like a job interview—there’s a goal in mind. Most of us are searching for that potential partner to spend the rest of our life with, so the sooner you’re able to weed out the losers and psychos, the better off you are. At the same time, it’s important to keep in mind that any of these questions can, and most likely will be fired right back at you. So be prepared.

Knock Yourself Out with These Ten Questions:

1. What was the worst thing you ever experienced and how did you handle it? A guy I dated in my early twenties was not over his parents’ divorce that happened when he was twelve. Seriously. He was still bitter and whined about it—nightly—while he threw back Bud Light after Bud Light. I didn’t see a future with us, only red flags. But, maybe your date has a legit situation, like the death of a family member or friend. That one probably deserves a pass.

2. Do you spend time alone … if so, how? It’s been my experience that people who don’t spend time alone are running from something, and it’s usually themselves. If someone constantly needs to be around others, there’s more going on underneath, most likely anxiety. It’s pretty cool when people are able meditate or sit with themselves and get to know who they really are. Because they’re more in tune with their body, they’ll be more apt to be in tune with yours as well, if you know what I mean.

3. What do you and your friends do when you hang out? My friend was recently asked out by a guy. He wanted her to go to an ugly sweater party, equipped with kegs, beer pong, and probably seven minutes in heaven. Who knows. The point is my friend is in her thirties and a little past this college-type behavior. What people do when they hang with their friends says a lot about who they are.

4. What do you do in your free time, when you’re not working? If she stammers and avoids eye contact it’s because she doesn’t have any free time. She’s always working. You will never see her. You’re probably on a lunch date right now. Of course, this could go the other way too—she may look at you uncomfortably because she’s thinking, Job? What job? But, if she answers with some hobbies/interests that appeal to you, you can exhale. Just remember, though, that you don’t have to have everything in common. Partners are supposed to compliment each other, not compete with one another. If you both like dark meat chicken, who’s gonna eat the white meat? And I’ve witnessed things get ugly between athletes who date one another.

5. Have you ever had your heart broken? This question will give you some insight into her past relationships and how she coped. A girl who has had her heart pummeled has some humility, which is attractive. And if she answers no, she’s either a liar or she hasn’t lived enough. So, maybe it’s your duty to show her what it feels like. I’m just sayin’.

6. What makes you vulnerable? Seriously, few things are sexier than vulnerability. A real woman knows how to make herself be vulnerable. That goes for men, too. Opening up can be a slow process, so getting an answer to this one may take time. Be patient.

7. What are your relationship deal-breakers? This is critical because, say, she hates cats. She’s allergic to them, in fact. And well, you own four and consider them your babies. This might be an issue. Some other deal-breakers might be if she doesn’t want children and you do, or she doesn’t like to be around alcohol and your best friend is a vodka tonic. It’s best to sort this stuff out now before any sort of feelings evolve.

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From Around the Web:
02.25.2011
Nikki Deterding
These are some great tips! Thanks!
It feels good to write.

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