20 Questions I Would Like to Ask on a First Date

First dates are like interviews.

At least in my experience. Every halfway decent one I’ve ever been on is a volley of questions, as if both parties are reporters and the person across the table is his or her subject. Except instead of writing about them, both people are tasked with trying to decide whether this person has enough potential to be included in future plans – whether that is a second date, a night of wild sex, and/or everlasting love.

But in my experience, these questions have been mostly softballs, like “Where do you work?” or “How many siblings do you have?” or “Are you going to pick up this check…?” (The last one is usually asked with the eyes.)

You get to really know a person more by either asking questions you actually want to know the answer to, or through the off-the-cuff answer they give when you ask them something they were absolutely not expecting.

So why waste time? I’m 25. The internal clock is ticking. I don’t have time to sit through all that mundane banter.

Here are some questions I would like to ask on a first date.

1. What if we connected tonight, and then got serious, but I eventually went bald?
2. Do you believe that Jadakiss is as hard as it gets? Why or why not?
3. How would you react if I told you the most unique thing about me is I have four nipples?
4. Check out how long my chest hair is…should I have trimmed it before this date? And do you see my extra nipples, right there and there?
5. Do you wear tights often? Do you realize the kind of power those things have? That they’re the sexiest, most form-revealing pant a woman can wear, but also arguably the simplest – conveying that the wearer may not be too pretentious about her public appearance while still showing off her splendid hindquarters?
6. Are you someone who likes to cuddle while sleeping? If so, do you find it gross to wake up in a puddle of your spooner’s sweat? It not, would you say it’s something that actually turns you on?
7. Are thongs more comfortable than other women’s undergarments? How does it feel to work out in them? Are you wearing one right now? If so, may I see it?
8. How would you feel about keeping your career while a man like myself left his behind to raise our children, providing only the modest income he receives from writing haikus for Highlights magazine?
9. What are your initial thoughts on a 25-year-old male who still sleeps with stuffed animals?
10. How many dates do you have to go on, or how close do you have to be with someone, before farting around each other is acceptable? How about pooping?
11. What is your preference – length or thickness? I’m talking about penises.
12. Have you ever found yourself in a position (as it were) where a safe word was warranted? If so, have you been checked for STDs since? And if so, what were the results?
13. Do you ever wonder what sex would be like if you were a dude? And, theoretically speaking, would you trade genitalia with a man for a day, just to feel what it was like to be on the opposite side of the mating spectrum?
14. If we were to enter a monogamous relationship, would you be into spicing things up by holding a “Bacon Day” every now and then, where we watch Kevin Bacon films while eating copious amounts of bacon, maybe in bed? And then once a year having a “Bacon Day Blowout” where we make a mattress of bacon and do with it whatever feels right?
15. How much scotch consumed on a daily basis would you say is too much?
16. If we go back to my place, will we bang? If not, can we please watch Die Hard? And if so, can we please watch Die Hard afterward if I don’t take too long (I won’t)?
17. Does the ability to masturbate whenever you want ever influence your decision to either go out or spend an entire weekend locked inside your apartment, only leaving to walk downstairs and make an exchange with the Chinese food deliveryman?
18. Since we’re friends on Facebook, I feel like I should ask: do you already know that I “like” a page called “Hot Girls With Glasses?” If so, would this have any bearing on whether you rock spectacles – with real prescription or otherwise – on our next date if one were to occur?
19. Are you turned off by random back hair?
20. Why are boobs good?

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