Ideally, a first date should be about getting to know the person. After all, why waste time moving forward in a relationship with someone with whom you have a serious and irrevocable incompatibility.
If you love all eight of your cats like children and he can’t even enter a house where a cat once lived without sneezing, thank him for the free drinks and cut your losses.
The struggle remains, however, how do you acquire knowledge about your date partner? While you don’t want this sit down to feel like an interrogation, to get to know this person, you do actually have to pose some questions. It’s not a job interview. You don’t want to ask him to calculate how many ping-pong balls can fill the bar, but you can ask simple questions without seeming too pushy if you ask the right ones.
1. What’s Your Favorite Book/Movie?
Not only is this question unintimidating, his answer to it tells you more than what movie or book he enjoyed. Without much effort, you can glean information from this answer. If he tells you he loves “Animal House”, you can deduce that he likes to party, which is great if this is the same for you. Conversely, if he declares his appreciation for “The Notebook,” you have a serious romantic on your hands, or admittedly someone who seriously wants to impress you.
2. What Are You Passionate About?
You let him stick his toe in the water and test it out with your easy first question; now encourage him to man-up and dive in by asking him something important. Not only will his answer to this question tell you if you care about similar things, it will also offer you the advantageous opportunity to engage in a conversation about something he cares about, as you can easily probe further or offer your own insight and experience with the topic about which he expresses passion for.
3. How Do You Feel About?
Now that you know what he cares about, you need to know how he feels about your passions. When posing this question, carefully avoid swaying his answer. Try your best not to indicate in any way that you care deeply about the cause about which you inquired. If you do, you increase the likelihood that he tells you what he thinks you want to hear instead of how he truly feels.
4. Are You An Early Bird Or A Night Owl?
If this goes well, you will likely want to spend copious amounts of time with this new partner in the very near future. While it doesn’t have to be a deal breaker, if you’re a crack-of-dawn riser and he slouches out of bed right before noon, it is helpful if you share a similar preference in this area.
5. Where Do You See Yourself In Five Years?
Everyone knows the best way to scare someone off on a first date: ask about the potential of having kids in the future. Even when asked in the most well intentioned manner, inquiring about marriage and kids or the ideal place for a destination wedding and the font you want to have on your return address labels once you’re married can be tremendously intimidating!
Try getting the information you desire about his ultimate wants in a less terror-inducing manner by simply inquiring as to his half-decade goals. If he is too uncomfortable, he will sidestep this question by talking about his career goals or his desire to move to Denver.
If he is comfortable with his ultimate relationship wants, he will likely speak more about his desire to find a life partner and begin a family.
6. Are There Any Foods You Don’t Eat?
This question is all about courtesy. Inquiring as to his food preferences not only allows the opportunity to share yours, which is particularly useful if you are a picky eater and you want to spare him the embarrassment of cooking you one of the million things you don’t eat, it also shows that you actually want to know who he is and what he likes.
7. What Do You Dislike Most About Dating?
Particularly if his answers to the previous questions indicate to you that he is someone with whom you can imagine a happily ever after, this question is crucial. Listen up as he tells you what other partners have done wrong and catalog what you hear so you can avoid these missteps as you move forward with him.
