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The 50 Most Important Questions To Ask A Date

December 6th, 2012 Leave a comment Go to comments

One of the steps people have to complete in order to participate in my blind date column at The New York Post is a questionnaire. The original questionnaire I inherited when I took this over was 40-questions and eople always told me the same thing: “Forty questions is a lot.”

I know. But it’s not more than sites like OkCupid. If the person didn’t over-think their answers, they would see it’s a fun way to get to know themselves. Sometimes I suggested people fill it out with a friend, just to make it more exciting.

But alas, whenever people reach out to express their interest in participating, I always lose them at the questionnaire. They either take a long time to fill it out and send it back or I just never hear back for them. So like most people who are always giving out their number or contact information only to not be getting any responses, I decided the problem was me and the questionnaire.

Forty questions does seem daunting, but not if the questions are fun, lighthearted, and interesting. On the old questionnaire, one of the first questions was simply, “Describe yourself…” Most people who get that question will be stuck, not because it’s a difficult question to answer, but it’s complicated. People don’t want to come off as too simple nor do they want to present themselves as complicated, so a question like that (which I know, it isn’t really a question) only begs for more questions.

So yeah, I changed up the phrasing and I moved it down to near the end of the questionnaire. Near the top of the questionnaire, after all the basic contact information is asked, we get into some easy but revealing questions. I thought this was also important because as we all know, sometimes one essay question can feel like 40 short questions. The ones I added were intended to make the questionnaire not feel as mountainous of a task as I got the sense it did for those who signed up. This is why the new questionnaire is 50 questions, but it doesn’t feel like it.

Below is the questionnaire annotated so you all can understand why I’ve included each question. Also, so you know, the purpose of the questionnaire is not only for the people picking to get to know who they’re picking, we also consolidate each one to craft the profile we run in the paper. For those interested in participating in Meet Market, you should know the rules by now, but just in case, here it goes:

Must be over 21
Must be single
Must live in NYC area
Must not be shy and willing to be photographed for the paper
Must be willing to go on a completely blind date and not be worried about what their date looks like, but just hope they’re as fun as them.

At the end of the questionnaire, serious applicants can download a copy and email me at But even if you don’t live in NYC, pass it on to someone who does and might be interested in participating or just answer some of the questions in the comments section.

Remember, these are the important questions we must all ask someone we’re dating. ENJOY!

1. First and last name:

2. Occupation (please list occupation as your title, NOT industry-e.g. “editor,” not “publishing”):

3. Contact info:
a. Address:
b: Phone:
c. Email:
d: Twitter handle:

4. D.O.B.

5. Current age:

These are the basic questions we use for our records. From this, we only use the first name and the age of the participants in the paper. We don’t share the contact information with the other dater. Whether or not you want the other person to have your information is decided by you on the date.

6. Where you’re originally from and how long have you been a New Yorker:
7. Where you live now:

NYC is filled with transients. You would be surprised how many people express their pride for where they’re from and where they live now when they answer this.

8. Ethnicity:

Since I made the decision to make the dates completely blind, I thought this was important to add. Another reason for this will be explained in a later question.

9. What’s the last book you read?

Notice I didn’t ask “when’s the last time you read a book”? Yeah, nobody cares, we’d just like to know you’ve read something.

10: What’s the last album you purchased/listened to?

The key to this question is in the phrasing. Too many favorites for people to list or think about. But everyone knows the last thing they listened to or purchased or illegally downloaded.

11. To what song do you know all the words?

Another question I feel is better than the normal, “What’s your favorite song?” Usually if you know all the words to the song, it’s one of your favorites.

12. What movie can you watch over and over again?

Mine is “Drumline,” “Casino,” “Goodfellas,” every “Step Up” movie, “Might Ducks,”. This is just way more fun than, “What’s your favorite movie?

13. What shows are on your DVR or are can’t miss television?

This one makes you think less of your favorite show and more of the one you’re always watching or recording, which can be mutually exclusive.

14. What’s your favorite sport to watch/to play (include teams if you’d like)?

A good question, especially for people who are sports fans. When I’m deciding on which people should be offered up as choices, I’m looking at little things like this to see if they have this in common. I personally would always give benefit of the doubt to a fellow Steelers fan.

15. What’s your favorite ice cream?

If you don’t think this question is important, you’re probably single.

16. What card or board game are you the champion at?

People love games, and they love winning at games. If I found two people who both said they were Scrabble champs, I’d put them in a position to choose one another. Then I’d send them out for a Scrabble date.

17. Can you dance?

I mean, if you don’t know how to dance, then you might be perfect for the other person who doesn’t know how to dance.

18. On a Friday night with friends, I’d rather go to a: movie, concert, sporting event, dive bar, lounge, big dance club, karaoke bar, other (please explain):

As the Notorious B.I.G. once said, “Ask you what your interests are, who you be with?”

19. Where’s your favorite place (bar, park, neighborhood, museum etc) in NYC and why?

This is a question I’m always using to help me plan the date for participants.

20. If you had to choose only one way to get around the city between walking/running, taxi, car, bus, or subway, which would you prefer and why?

I’m personally a subway guy because I find the theater of the passengers thrilling, but this question’s answers can say a lot about people.

21. Why are you a catch? Impress me.

I inherited this one and I’m glad I did. The answers to this make me lol, literally. This also gives people a chance to describe themselves creatively.

22. What turns you on?

23. What turns you off?


24. What is your biggest flaw (physical or otherwise)?

You’d be surprised how hard people are on themselves with this one.

25. With who, what, or when are you your happiest?

This one gets people all sappy and sometimes nostalgic. Melts my heart sometimes.

26. Window seat or aisle seat?

If you go out with someone else who likes the window, how do you decide who gets it? You have to think about these things, people!

27. Describe your ideal date night or day (Where would you go, what would you do?):

Another question that helps me plan the date.

28. Biggest pet peeve:

29. What’s something most people don’t know about you?

Some basic, fun questions.

30. Are you ready for the zombie apocalypse? (If you have to think about it, you’re probably not, so feel free to skip):

There are a bunch people for whom this answer is going to be a huge factor before they decide if this person is right to date. What if the zombie apocalypse happens on the date?!

31. What’s your guilty pleasure (snack, TV show, music, clothing, etc.)?

32. It’s silly, but I’m afraid of (explain)…

33. What drink do you always order first at a bar?

34. If I were to raid your apartment right now, what’s the most embarrassing thing AND the coolest thing I’d find?

35. Best make-out music (or song):

These questions offer me a chance to use interesting artwork when we’re creating the profiles. I always enjoy the wide-range of answers I get with each one.

36. What’s the nicest thing a non-family member has ever said to you?

This is for you, the people answering, to smile. I’m sure once you remember that compliment, you’ll be grinning.

37. Celebrity people say you resemble:

A little tip here: Let’s say you look like Phillip Seymour Hoffman. Leave this one blank

38. Who’s your celebrity crush?

One time a guy put Raven Symone. I was laughing and kind of freaked out, but technically she is over 18, so it’s fair.

39. Describe yourself (be as specific as possible, these are real blind dates, so this is your chance to talk yourself up to the person choosing):

Body type (e.g. athletic, full-figured, skinny, big sexy/beauty):
How you rate yourself (e.g., good-looking, cute, average, aquired taste):
Tell us more…

Party animal/Social:
Chill/laid back:
Tell us more…

40. Describe the type of person you’re looking to date (physically AND personality-wise):

As I said, these originally were at the top of the questionnaire, but I put them here because if you’ve gotten this far, you’re probably ready to knock these out. I think I gave folks enough to work with and I’m hoping they give me enough so I can describe them to the other person on the blind date. These are the most important questions

41. In what ways do you want your date to be different from you?

This where short people like to say, “I’d like them to be taller than me.” I hear you short people.

42. What or who makes you laugh (e.g. puns, a specific comedian)?

People have sent in some funny YouTube clips on this one. Thank you

43. In what ways would you say you are very ‘New York’?

If you didn’t fill this one out, and you just skipped it, you’re rude. That would make you very “New York.”

44. Pets: Woof, Meow, Other/Neither, Allergic:

I’m allergic to cats. Every woman I date needs to know this.

45. Favorite kind of food (Italian, Mexican, Sushi, etc):

46. Any dietary restrictions we should know about (Kosher, Vegetarian, Vegan, etc.):

Most of the dates I plan take place at a restaurant. I use the answers to this question to help me make a good decision as to where to send the daters.

47. Are race, religion or age important factors regarding who you date? (This won’t be published, but is important so we know who you’re looking for)

This is the question I skip to whenever people return the questionnaire to me. It’s probably one of the most important. Remember when I was talking about the ethnicity question. This is the reason I asked it. You would be surprised at how open people aren’t. And that’s fine. There is someone for everyone. But I’m always relieved and better able to get people on their date when someone simply answers, “No.”

48. How would you describe what you are looking for with this experience? Just want to have a fun night? Looking for a repeat date? Someone for the long haul?

I’m sensitive to these answers. I always like to know what people are trying to get out of it.

49. Anything else we forgot to ask?

50. After your date, is it ok if we contact you in the following months to follow up?

See? That isn’t so bad, right? I think it’s easy and fun. Like I said, for anyone who wants to participate or knows someone who does and they live in NYC, please, click on the link to download (it’s formatted in Word) and send it to me at

Download the Meet Market Questionnaire

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  • Champ Ion

    My best friend and I sat down and she and I did something similar, only we got to 79, as we intended to go for 100. Just to have something to talk about in case the conversation went into a lull we she or I had a respective date…. so we’ll be stealing some of these. And kudos to the last 3 posts (including this one). As a single almost 30 something (29), I saw a lot of things that I’ve experienced and they were all thought provoking reads that I got something from, but the I generally enjoy all your posts. Propz homie!

  • Guest

    There have been so many (too many) articles on how no one wants to date black women. Have you found this to be the case from your Meet Market sample?

  • alix

    Good Questions its hard to go on a blind date, more so for men. But once you let go i’m sure its fun.

  • Nikki

    ….pops popcorn, and waits…..

  • Steph

    Good questions, makes you think. I still wouldn’t fill it out lol