Questions to Ask on a First Date

First dates are full of nerves, excitement and if we’re being honest, a spark of hope that this guy/gal might be the one. We’re usually afraid of saying something wrong and looking like a total loser before we’ve even finished the first drink!
Though you could write these out in a list and bring them along on your first date, I don’t recommend it (remember the loser thing? Yeah, you really don’t want to be one of those). Instead, I suggest that you pick the ones most important to you and use them as conversation starters.
There are two things that you have to keep in mind. First, not everyone will answer truthfully on the first date. Some people prefer to keep these answers until they know the other person better; others have no problem just jumping right in. And second, if you ask the question of someone, you have to be prepared to answer it yourself. In other words, play fair.

If you could be anything you wanted, what would it be?
Here’s a great test of someone’s imagination and sense of humor. It will also show you what motivates them. Listen carefully and you’ll be able to tell if they’re driven by money, intellect, or curiosity. It can showcase hidden ambition, creativity and spontaneity. I once had a first date where this was the only question I asked. Once we started discussing it, we couldn’t stop!

Has your heart ever been broken? 
Most people, if they’re being honest at least, will answer “Yes”. Depending on how long ago, their answer may be accompanied by pained sighs and haunted eyes. If the heartbreak was recent, be warned; you don’t want to end up being rebound guy/gal if you’re really looking for something more serious. The more defensive a person is, the more likely they are to answer “No”, as if having their heart broken is something unacceptable that shouldn’t even be discussed in polite company.

What do you like to do for fun? 
If you’re the outdoorsy type, chances are you’re not going to hit it off with someone whose idea of a good time is Saturday afternoon cartoons. Likewise if you like to cuddle in front of the fire on a cold snowy winter afternoon and he/she prefers to hit the slopes, you might not have as much in common as you’d like. 

What’s the most interesting place you’ve ever visited? 
A great question to figure out if you’re sitting across from a confident world traveler who likes an adventure or if you’ve just met a more cautious type who prefers to stay close to home. Keep in mind though that travelling can be expensive and not everyone can afford to go wherever they want, whenever they want.l

What do you think is the biggest mistake people make on a first date? 
If you’re looking for some insight from the opposite sex, then ask this question. If the person you’ve asked has had a lot of dating experience, some of the stories you’ll hear will probably have you cringing in shared embarrassment, howling with laughter and maybe even both. Of course they could also answer “asking stupid questions” in which case you should simply pay for your coffee and leave; they obviously have no sense of humor at all!

What do you think is the biggest mistake that people make in a relationship? 
The answer to this should be a little more in depth than the previous question, for obvious reasons! It should give you a very good idea of your date’s views on gender issues, turnons and turnoffs.

Have you ever gone out with a guy/gal who was a real challenge? 
If the answer to this one is “Yes” find out why he/she thought this person was a challenge and more importantly, how he/she handled it.

What’s the one thing you just can’t resist? 
This is the question to ask to find out what someone really REALLY enjoys. The answer might surprise, delight or even annoy you, but that’s the chance you take. Besides, first dates are all about finding out about someone.

If you could change one thing about yourself, what would it be? 
Their answer is an excellent thermostat to their self esteem. Someone who is focused solely on the physical will likely respond with something like “I wish I was taller/shorter/fatter/thinner “; well, you get the idea. If all you hear is a litany of what they think is wrong with them, be careful. Dating someone without a shred of self confidence isn’t going to be a laugh a minute.