My Awesomely Random Life (and Everything in Between)


So you’re going on a first date with that super cute guy/girl from your office. Supe’s exciting!!!! But before we get too ahead of ourselves, let’s run through the dating check-list, shall we?

You’ve showered.

You’ve picked out the winning outfit that screams “Oh this old thing? I just threw it together.” *You actually spent 59 minutes tornadoing through your closet and after realizing that you literally didn’t have anything to wear, you made a last minute trip to Target, spending last week’s pay check on just all of the things.

You’ve blushed, bronzed, polished, shaved, waxed and groomed. You’ve used so much hair product and perfume/cologne that it would be well advised not to get within 50ft. of any flames. You want to look hot, but like, not ‘caught on fire’ hot.

You’re ready to do this thing!

But wait just a second.

What happens when you actually get there? You’re going to that new pizza place downtown so there will definitely be eating  involved (oh, there will be eating), and probably a few drinks. But at some point, there’s going to be a time when you’re mouth isn’t stuffed with pepperoni deliciousness, when your Diet Coke is awaiting a refill, when you actually, gasp, have to make some kind of conversation.

I know.


But don’t you fret, my friends. I got you.

First dates, to me, can be both equal parts nerve-wracking, exciting and to be honest, kind of boring. As we discussed here, there is a sort of formula that first dates follow. More often than not, this formula consists of a cheesy movie, followed by an even cheesier dinner (especially if you’re eating at that new pizza place downtown–they do NOT skimp on the fresh mozz, let me tell you!) and then a series of pre-planned, standardized, get-to-know-each-other questions ala “What do you do?”, “Where did you grow up?” and “What kinds of music do you like to listen to?” (among others).

While there is absolutely nothing wrong with breaking the ice with these kinds of questions, there’s also nothing too terribly exciting about them either. If first dates are a time when you’re supposed to find out if you and your potential SO have anything in common, if you are compatible, if you agree on the really important things in life, than shouldn’t you be asking the hard-hitting questions instead? I mean, this could be the person you end up spending the rest of your life with!

Or at the very least your Friday night (which is precious prime Netflix/ ice cream and book-a-thon time, mind you).

The following is a list of the 20 vital and absolutely necessary questions you should be asking on your next first date:

1. How many times a day do you try and use The Force?

2. Gun to your head, you must choose one: Oreos or Chips-a-Hoy?

3. What’s your opinion on sweatpants?

4. So, do you cheat when playing Monopoly most of the time or all of the time?

5. Are you more of a Chandler, Ross or Joey?

6. On a scale of 1-10, how much do you drench your pancakes in syrup? (1 being “a lot” and 10 being “syrup with a side of pancakes.”)

7. On average, how many hashtags do you include on an Instagram photo?

8. Who’s your favorite Game of Thrones character? Jon Snow? Or Jon Snow?

9. At what point in the afternoon do you change out of your pajamas?

10. Who are your favorite celebrity twins and roughly how many days has it been since you last watched Passport to Paris?

11. Was Leo still in a dream at the end of Inception?

12. How many sauce packets do you ask for with an order of chicken nuggets?

13. Which Disney villain would you play tetherball with?

14. Favorite Starburst color on three. One, two, YELLOW!

15. Do you dogear your book pages?

16. What’s your go-to ugly car dancing and karaoke jam?

17. Would you say that Cloris Leachman is basically Betty White’s rebellious cousin?

18. You spot a terrifying spider the size of a small burrito a foot away from you. How do you react?

19. Speaking of burritos…what would you include in your ultimate tortilla-blanketed masterpiece?

20. Do you mind if I have that last piece of pizza?

So there you have it, folks.

The ultimate (and tres important) list of vital and absolutely necessary questions to ask on a first date.

Now go forth, use The Force, and make me proud!

And if you can, snab me a slice or two! 😉


Comments on: "20 Vital and Absolutely Necessary Questions to Ask on a First Date" (9)

  1. Bahahahaha! Ah Wendi you always make me laugh! I love your sense of humour! X

  2. You are such a goober. You must have the guys lining up around the block to go on a date with you. 🙂

  3. This is where I’ve been going wrong! I’ll have to line up a date next week and try these out. 😉 Thanks!

  4. These are all brilliant questions!
    And the answer to #2 is obviously Oreos … unless you’re talking Rainbow Chips Ahoy in which case that’s a whole other thing.
    … Finally, I’m pretty sure #13 is the best question of all time. So many epic options!

  5. Haha, love it! I always say that dates should start with a questionnaire that each person should fill out just to make sure if it’s actually going to work out or not.

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