Questions to Ask on a Blind Date (Good or Bad Icebreakers?)

0 Posted by - November 2, 2009 - Uncategorized


Some of you might remember a while back when I went on my first blind/speed-date. It was part of a collaboration between Glamour magazine and Skype. The whole thing was recorded via Skype cam and posted on so people could vote on which of the three bachelors should go on a real-life date.

If you missed it, you can CLICK HERE for footage of the blind date.

In preparation for the date, Glamour editors suggested that all bachelors come up with a bunch of off the wall questions. The point was to make your 20 minutes of face time exciting and different. Basically, they wanted to avoid asking the cliché what-do-you-do-for-fun or what’s-you-favorite-color questions.

Needless to say there were a few technical difficulties with the Internet connection and things fell behind schedule so my 20 minutes got cut down to about seven. At that fast pace, Erin the bachelorette, who was actually a relationship blogger, steered much of the conversation and most of the questions I drafted got thrown out the window.

Well, I was cleaning out my BlackBerry the other day and came across my list of blind date questions. Some of them are funny, some are thoughtful and others are just plain weird (i.e. No. 1), but, hey, they’d probably all get a conversation started—I hope.

Since I never got to use them I figured I’d run them past y’all for some feedback and future blind date conversation fodder. So without further ado, here are…

NWSO’s Random Blind Date Questions

1. Apple juice or orange juice?

2. When was your last vacation and where did you go?

3. What’s your favorite place in the world?

4. What do your parents do for a living?

5. Which Sex in the City character are you most like? Why?

6. How many times have you been in love?

7. What’s your longest relationship?

8. Who was your favorite teacher in elementary school?

9. What’s your biggest pet peeve?

10. Have you ever stolen anything?

11. Do you recycle?

12. What’s the longest you’ve ever owned an umbrella for?

13. Who are you going to be for Halloween this year?

14. What hat size are you?

15. Do you own a power drill?

16. High heels or flats?

17. Are you a Mac girl or PC girl?

18. When was the last time you cried?

19. Peanut butter and jelly or milk and cookies?

20. So when’s our next date?

What did you think of the random questions? Do you think they’d make for interesting icebreakers on a blind date? Were any of them corny? Do you think my blind date would have gone better if I had a chance to ask some of these questions? Would you use any of these on a first date? What topics are off limits for you on a first/blind date? What’s the wildest thing someone has said to you on a first date? Have you ever gone on a blind date? If so, was it hard striking up a conversation?

Speak your piece…

What do you do

  • da ThRONe

    Pointing the corny finger @ Ans! LOL (I havent forgetten about the corny finger)

    I dont do ice breakers. My whole personality is an ice breaker. Im never at a lost for words unless I want to.

    I dont think anything is “Off Limits” at the sametime I dont like being sized up in the first five minutes. Lets just enjoy each others company (or atleast try) before we decide weither we’re soulmates or not. I think before people relationship becomes intimate they should establish a friendship.

  • Lonias

    #s 6&18 are smart questions to ask. I think the answers could be very telling about character and compatibility. #12 just made me laugh out loud!

    As far as your blind date, I think it would have gone much better if both of you had had a chance at bat. She ended up carrying the whole thing & that put you at a disadvantage. IMO

    I answered a forum along this same line on another site, and original poster asked for 10 questions. Here a few I would ask:
    -Are you doing what you thought you would be doing at this time in your life?

    -What do you still dream about doing?

    -What’s on your iPOD/in your CD player in heavy rotation?

  • NWSO

    @da thRONe

    Blah, blah.

    What you doing here early anyway? Damn, daylight savings time set my post off early. No fair.


  • virtue5

    these questions are actually pretty creative and might make me think that the person asking them really knew how to think out of the box, so that would give them some bonus points. however, the power drill question is really random lol.

  • GV1584

    Those were pretty cool! Gosh I wish more guys would prepare their own lists like this! Except for the ‘when did u last cry’ question (which can be a little too personal for a first date IMO!) the rest would definitely get me talking and laughing (power drill!?) lol

  • Elle

    Except the “when did you last cry” question those are some pretty interesting and “out of the box” questions I am sure a lot of people would appreciate on any first date – blind or not.

    I love Number 12 … LoL. That’s a good one.

    Generally, creativity ranks verrrrry high with me and I am sure with most people. So yup, I guess we all should come up with similar questions next time we go on a date. Matter of fact, I think I will steal yours *yoink* :P

    Personally, I am an open book. With me it’s like “ask away”, I am not ashamed. Nothing is really off limits. If a guy wants to get to know the real Elle, he shall get the real Elle. Hopefully, he can take it. Because as open and as blunt as I am about myself, I am the same way in regards to asking him some way out questions. If he thinks that’s too personal, ok, I am not dying for an answer but it would raise an eyebrow with me. This is besides the point though.

    During my first, real convo with my ex he told me he had slept with a tranny before when he was going through a rough time in his life and was tryng to figure his place in this world out.
    I didn’t freak out about it at that time because I thought it was super honest and I appreciated the fact that he confided in me with something so personal. Especially, since he had never told anybody else about this. But I must admit I could never get this out of my head again and always wondered if he is “in the closet” or has a preference for transsexuals but is too afraid to live it openly.

  • NWSO

    @virtue5 & GV1584

    The power drill thing is actually based on something a girl told me. She was like every woman should own a power drill in case you have to put something up. At the time I didn’t have a power drill. Needless to say I do now (two in fact). LOL

    Think that’d def start a conversation on why you should or shouldn’t have one. Def silly banter would ensue and break ice

  • BMW2K

    I have never gone on a blind date, but I like the questions. As a matter of fact, I think the questions are good questions for any first date because some of the answers could be quite telling. Additionally some of them add some serious humor.

    I LUV #15. There is something sexy about a man who knows how to fix stuff. ;-)

    I do like the IPod/MP4 question that Lonias suggested . . . I would add that to the list. I might also add something about the last book they read or their favorite blog. I like to know what people are reading.

  • Righteous Mama

    These are much better questions than I’ve been asked lately. I am sooo tired of the what do you do what kind of music do you like questions. These are good and will def help start up interesting convo. My favorite question is who was your favorite elementary school teacher. Funny how much I remember her. No one ever asks about things like that. Nice.

  • Chanel

    I like these questions — except one. Maybe it’s because I was a writer in NYC for so long and got so sick of friends calling me Carrie all the damn time (for one thing, I’m black and for another, if I was that successful at my career I wouldn’t be dumb enough to spend all my $$$ on Blahniks!), but asking me about Sex and the City characters would get you a (slightly) good-natured icegrill from me.

    The iPod question is great, as long as you’re not using it as some sort of hipster litmus test. I got a great variation on that question from a colleague. He asked me to name the 5 albums I’d listen to if I was stuck on a desert island. I had to really think about that one and it was a definite icebreaker!

  • Shequita

    I love the questions! I like for ppl to ask different questions! I think some of them might’ve been too personal for a first date for some ppl but they’d definitly strike up convo!
    I find myslef asking crazy questions too, being yourself (I’m randomly silly) really does weed out the potentials from the “keep it movin’s.”

  • Cali

    The questions were pretty good. However I would never use them on a date or a blind date. It’s easier to go with the flow of things. U don’t want to be sitting up asking a person questions and them feeling like there on the witness stand. Plus by them answering them is still not telling you a whole lot. That person could be lying or anything. Why not just feel out the questions in a conversation you all might have. That way u can kind of get a better sense then just putting a person on display with there whole personal life. I say good questions but screw them, let the conversation just flow easssyyyy! If it doesn’t work, I mean no conversation or anything and you both are just sitting there looking crazy just get up, leave they ass, & never call they ass again! JUST KIDDING! Just make the best of the nite.

  • Sweet Nectar

    One time I was on a date with this sexy, intelligent, articulate man who I was simply smitten by. We went through the gammut of typical first date questions. When he asked me if I was on birth control? What kind and how long? I was so shocked I had to pick my mouth of the table. Needless to say our courtship was short-lived.

  • grownandsexy83

    These are better than most questions you get during a first/blind date. They would definitely be good ice breakers and the topics would make that person stand out. Yes, I have had a blind date before and it was horrible. Nothing to talk about, just sitting there like “I could of had a V8!” I don’t think any of the questions were corny but 1 and 12 are just a bit weird. Great post!

  • Mshollywood

    How about something a guy shared with me without asking (damn has it got to the point we actually have to ask this lmao)
    the guy told me that his parents raised him in a satanic cult WTF!!!!!!!!

  • Aaviana

    My fave question that I was ever asked was “So you like guys and girls right”? LOL. He follows me on twitter and wasn’t for sure about me.

  • Sidnei

    im making a mental note on some of these questions..i have a first date this week coming up!!!!

  • Anonymous

    Got a date on Thursday. Will be stealing from you. ;-)

  • YoungJay

    These questions are dope…Imma def add some of these to the reserve.

    @ Elle

    You are definitely a strong individual to accept that about ur ex cuz that is side-eye material at it’s best

  • Tasha Mack

    Many of these question are my ice questions or some form of them. I dont like asking the nor question! Love the list!

  • Elle


    Thank you. Like I said I thought the fact he confided in my with such info spoke volumes about his honesty. And 100% honesty is hard to come by these days when people tend to send their representatives to the first 50 dates.



  • da ThRONe


    That is wild though. But I will agree I think honesty is huge when you can get it. Too bad most people cant handle it which force most to be fake.

    Did he leave you for a Tranny? He should come to N.O. he would have a field day. LOL!

  • Elle

    @ da ThRONe

    Yeah, honesty is key. I am a very understanding and empathic person who can deal with almost everything under the sun as long as I know about. But hiding in hopes of me not finding out feels like an insult to a) my understanding nature and b) my intelligence. And I do not take being “insulted” too well.

    :| noooo, he did not leave me for anyone else.
    Self-esteem issues can lead people to do some way out things.

  • da ThRONe


    Yeah like sleep with dudes that think their women! LOL! Ok thats my last one.

  • da ThRONe


    As far as people not being up front you shouldnt take it personally. Like I said most people might not be as accepting as you and I are. I for one hate having my intelligence insulted but I can understand how hard it must be to bare your soul to somebody you like and your trying to get to know better.

  • Elle

    @da ThRONe

    Yeah, you are right, people are used to being judged etc. by others.
    But I think as adults we shouldn’t give a flying phucc (excuse my French) about what others think about us. It’s a matter of strength and integrity IMO.

    I do me and what I feel is right 100% of the time despite the outside world thinking I am crazy, stupid, selfish, naive, risk-happy or whatever the case may be. I stand behind everything I do and say. So on that note, I want to be in a relationship with a person who displays the same kind of approach to life. I try to avoid people who fold under (societal) pressure at all cost. But that is just a personal preference.

    So while a confession like the one I mentioned definitely falls into the side-eye material category, it made me respect him that much more because he displayed strength (besides honesty) in telling me about his “darkest secret” at the risk of being judged and discarded. He was being true to himself and I love that about any person.

    Ok, enough preaching.


  • Gemini

    Do You Recycle????

  • JuneBug

    Adding a question to the list:

    What’s the one item that you own that you absolutely cannot live without?

  • AnonyMiss

    I like all of these and I think if you were to ask the “when did you last cry” question, it’d best be the last one. Then you get to console her and you know the rest…. lol

  • Leo

    It kind of answer are good but I will say when I was in blind date.
    Do you have any sister sooooo I go 4 blind date????

  • Todd

    This is actually a pretty hilarious short video about a blind date.