Questions You Should NEVER Ask On A First Date

bad dateI’ve been seeing a lot of items posted on social media recently about the questions you need to ask on a first date, Modern Philosophers.

I’d like to share some of the research I’ve been doing since I’ve been back out there on the dating scene.

I’ve also compiled a list of first date questions, but since I like to put my own unique spin on things, my list is of queries you should NEVER make on a first date.

These are more like fourth or fifth date material, which would come in handy if I ever actually made it that far.

Maybe someday.  A guy can hope, right?

As always when I write a dating tips post, since I am a man who is interested in dating women, I will refer to the date with female pronouns for the sake of convenience.  There is no sexism intended.

These tips are for both men and women.  Hope they come in handy!

date 1Are you willing to waive your right to counsel?  While this might seem like the ideal ice breaker for a first date, I’ve come to find that it makes women uneasy.

I’ve always said I feel that a first date is like an interrogation, so that’s what makes this one hilarious to me.

Not so much to my dates, though.  I’ve finally stopped using it altogether.

Do you mind giving me a blood and DNA sample?  You’d think any person would be concerned with safety when meeting a stranger for the first time, but apparently, this question either creeps out or offends my dates.

However, there was one date who had the samples handy, which was a big plus in my book.  That is, until we got a hit on her in CODIS for an unsolved murder in Idaho.

Needless to say, there was no second date with her.  The silver lining, though, being that the reward money I received for information leading to her arrest did help me finance several more failed first dates.

date 6Did  you know that polygamy is legal in some states?  While I only meant the question to show that I am open minded and knowledgeable of other belief systems, the dates I asked this one assumed it meant I wanted to have multiple wives.

This is what happens when you jump to conclusions, folks!

Is it okay if your ex joins us?  If a first date were a job interview, she would expect me to check her references.  Why can’t I do that with dating?  I thought it was a great way for someone who knew my dates to speak highly of them and give them glowing reviews.  How was I supposed to know they had ended things poorly?

What about bonus points for doing the research and finding out about your background?

Are you like me in that you prefer a June wedding?  I actually had a date get up from the table and never return after I asked that question.  I get it, you don’t like June, but did you have to ditch me in the middle of a date because we didn’t see eye to eye on one little detail?

I’ve taken to editing this question to the more acceptable: In what month would you prefer to get married?  I guess it is more open minded of me to not push my preference on a date by wording the question the original way.  Lesson learned.

date 2Do you like bad boys?  If so, where do you draw the line on someone being too bad?  I’m not really sure what was wrong with this one, but it led to a lot of confused looks and phone calls to friends to let them know exactly where we were and to give them a detailed description of me.  Weird, right?

Does this look infected to you?  This one is obvious to me now, but at the time, I was just concerned and didn’t want to go to Walk In Care on the weekend if it really wasn’t necessary.  You live and learn.

For the record, it was NOT infected.

Could you cut my steak?  I ask because it’s a condition of my parole that I cannot be in possession of any sharp objects.  I just wanted to see how she’d react.  If she was biased towards people with a criminal past, I don’t think she is open minded enough to be the mother of my children.

What’s wrong with that logic?  Plus, I’m actually a total klutz and probably would end up cutting myself given the size of the steak knives they have at restaurants these days!

date 3Can your car’s trunk fit a body?  I’d like to travel, so if her trunk is big enough to fit a body, I know it would be able to handle all the luggage we’d need for a long vacation.

In hindsight, I probably should’ve simply asked if her car had a large trunk, but I was really afraid she’d take that to mean I was discreetly asking about anal sex.

Wanna see my prison tats?  I’d just watched several episodes of Oz and then had a couple of beers.  I usually get flirty when I’m tipsy, but I guess in this case, I took on the persona of a hardened criminal.

Let’s just say she got the wrong idea and totally tried to have her way with me in the car on the drive home.  I am NOT that kind of first date!

How come you went with a rug in the upstairs hallway when the rest of your home is all beautiful hardwood floors?  Apparently, it’s a negative thing to find out where your date lives, and have a look around by posing as a building inspector checking for mold, and convincing the trusting old lady next door who has the spare key to allow you into the house.

Excuse me for wanting to get to know you a little better so we’d have something to talk about on our first date, rather than have it turn into an interrogation.

date 5Would you mind signing this non-disclosure agreement?  I have a popular blog, so I can’t have my dates going onto social media and giving away the research I’m doing for future posts.

I need the goings on of our date to remain a secret until I’m ready to blab about it to my nearly 13,000 followers, thank you very much.  I’m sorry if that unnerves you.

The list of questions goes on and on, but I’m going to stop here.  I’m sure there will be future posts on this topic.  Hope this information comes in handy on your next first date.

It’s definitely helping me to understand why I go on so few second dates…

About Austin

Native New Yorker who's fled to the quiet life in Maine. I write movies, root for the Yankees, and shovel lots of snow.
This entry was posted in Dating, Humor, Love, Philosophy and tagged , , , , , , , , , , . Bookmark the permalink.

82 Responses to Questions You Should NEVER Ask On A First Date

  1. gh0stpupp3t says:

    LOL That is the best. EVER. 🙂

  2. D. Parker says:

    It’s all so clear now…I have to change my dating style. Thank you, Austin, you’re a life-saver, dating-wise. 😉

  3. floridaborne says:

    Man, I was ready to get up from my computer while reading those. You certainly did compile quite a list of button-pushers.

    I had one man ask me to be tested for venereal diseases. Some first date that was!

  4. biographyguy says:

    This was very funny. Cool post.

  5. Pamela Edwards says:

    Austin this is priceless !! Loved it !

  6. I’m so glad I am no longer on the dating scene. How would I ever find someone if I couldn’t ask these simple questions?

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  8. hollie says:

    Ok so when I read “is it okay if your ex joins us” I immediately thought threesome. I was like, wow, Austin I had no idea! Also, I did have someone show me legit prison tats on a date once. yeah….

  9. amommasview says:

    Hehehehehe!!!! Another bestseller in the making 🙂 😂😂😂😂

  10. Here’s one that somebody said to me once (just joking, of course — he was so funny). He folded a napkin into a pretty rose and said “Smell it! Does it smell like chloroform?” I still laugh at that to this day.

  11. Ramya says:

    Hhaha amusing!!

  12. henriettamross14 says:

    Eh? Yes!

  13. grannyK says:

    Well, it looks like you have learned from your mistakes! I’m glad I’m not trying to date! It sounds tough!

  14. The Chaos Realm says:

    ROFL! A morning laugh over tea!

  15. jaypochapin says:

    As a (happily) married man, I was grateful to relive many of my own past gaffes… Happy Mothers’ Day, Mod Phil!

  16. JED says:

    If I had these questions years ago it would have saved a lot of time. Luckily my wife was willing to work with my stupidity and still does to this day. No more first dates for me.

    I might change them a bit and use them for new hires. You think “Can I see your tat’s” or “Have you ever tested the size of your trunk for larger items” would work in a job interview?

  17. AthenaC says:

    I’ve found that you can get away with most of these (not all but most) if you are much more physically attractive then your date. Your date will often be so grateful for your attention that they are willing to overlook quite a bit. So maybe you just need to change the type of person you date!

  18. Haha! This has made my day. I especially like “Can your car’s trunk fit a body?”

    I’m so glad I left that whole dating scene along time ago!

  19. alundeberg says:

    Have you seen the movie Amazon Women on the Moon? There’s a great skit with Steve Gutenberg where his date runs his credit card to get his dating history– of course, his date goes downhill from there. Very funny– much like this post.

  20. newworldmom says:

    Does this look infected? LMAO!

  21. kriskkaria says:

    Hilarious! Can I narrate it for my podcast?

  22. Pingback: My Picks Of The Week #21 | A Momma's View

  23. berryduchess says:

    Haha! Or this can also be the things you can say if you dont want a second date :))

  24. Glad you shared some of these. I’ll keep them in mind for future reference. I’ve heard a few almost as weird. I’m sure a lot of women could share some doozies.

  25. nolanwrites says:

    Hahaha! Oh my Gosh Austin, did you really ask these questions on first dates? Hilarious! 🙂 Hopefully you have learned from your mistakes! Very funny indeed!

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