The 10 Worst Questions I Have Been Asked On A First Date

The 10 Worst Questions I Have Been Asked On A First Date

I’m kind of getting a reputation for being a bit of a serial dater, and honestly with good reason. I date a pretty fair amount. Once you get over the “will it be awkward?” panic everyone goes through before a first date, I think dating can be really fun.

But when you date a lot, you go on a lot of not-so-great dates. I think there’s a saying about kissing a lot of frogs that’s sort of applicable, but I don’t like fake inspirational quotes from Ghandi, so I’ll spare you. Whether it be to lack of chemistry, too much (or too little) alcohol, or just general douche-baggery, I have had some doozies of a first date.

The thing that blows my mind the most though, aside from the men with an inability to hold down their liquor who still chew with their mouths open, are the questions some people think are totally okay to ask. They aren’t even the questions that may seem invasive but actually everyone would love to throw out there, they’re just downright rude. Sometimes I snap out a come back, but often times I’m just sitting there staring at my beer, wishing I had filmed that interaction so I could send it to his mother and say, “You proud, hun?”

1. “What’s your number?”

Unless you mean phone number because you aren’t sure that you have the right one because I didn’t text you back because I was putting you in purgatory, you have no business asking that question. What’s yours? How much did you add/subtract from it? HMMMM!? And honestly, what is the “I hope she says this” answer you were looking for? Do you think you’re going to be the first? Do you want to be that guy? We’re both in our twenties and single, and you don’t want the answer to that question regardless of what it is.

2. “How much is your rent?”

Yup, my apartment is sick and I have a beautiful rooftop. It’s nice, I know. But it’s none of your damn business how much money I cry away at the 1st of every month. If you ask me this, you’re basically telling me your idea of a good time is sitting down and talking about our bills over dinner. It also comes across as your subtle way of hinting that I should pick up the check because I can obviously afford it since I don’t have a roommate. Not taking that bait, bucko. We’ll be splitting it down the middle like I always do on first dates, and I’ll be ignoring your drunk texts from here on out.

3. “You’re so short, can I pick you up?”

4. “Have you ever hooked up with a girl?”
Honorable mention is, “Have you ever been in a threesome?”

Do you honestly think I’m going to give you any stories for your jerk it rolodex? Smooth out the wrinkles on your khakis and keep walking because there is nothing here for you.

Guys, if a girl doesn’t offer up information about her sex life (current or past), it’s really not your place to ask about it. Take that info, put it in your back pocket, and save it for the next time you think about opening your mouth.

5. “Dude he sounds awesome, when can I meet your dad?”

WOAH. Pump the brakes, please and thank you. We literally just met and you’re asking when you can come back to mom and dad? You do realize you’re asking this AFTER I told you a story about how he shot skunks from our deck while sitting in a lawn chair, right? If he had zero problem shooting Flower from Bambi in front of his elementary aged daughter, think of what he will have no problem doing to YOU if I tell him about the threesome question. Still want to meet him?

6. “Did you lose/gain weight since you took those pictures?”

I don’t know, did your hairline start receding since you took yours?

7. “Can I stay at your place tonight so I don’t have to worry about driving home?”

Absolutely not. No sleepovers until we have discussed the ground rules, and I’ve decided you aren’t going to like…Snapchat me while I’m sleeping or some shit. I’m not falling for the “I’ll just crash on your couch” line. You’re creepy. I’m calling an Uber, no not for you, and Irish Goodbye-ing this situation STAT.

8. “Are you going to write about me?”

Probably not, actually. Except for in this sentence because you’re annoying and predictable with your lame-ass questions.

9. “Is this the nicest place a guy has ever taken you to or what?”

Is this the first time you’ve been let out into public, or what? I’m not impressed that you took me somewhere with cloth napkins and wine that doesn’t come in a jug with the Carlo Rossi sticker peeled off. I have been to restaurants with a dress code before. Shocker, I know. You can wave your wallet around as much as you want, but in the words of Miss Shania Twain: that don’t impress me much.

10. “Why are you single?”

Uh…same question? I get you’re probably looking for the standard, “I’m just focused on my career” answer or the idealistic, “I’m just waiting for the right person” response, but all you’re really doing is making me want to crawl back into my bed with my dog and my laptop and die alone so I don’t have to deal with people like you. That question makes every girl go through her dating history, her break ups, and relive those terrible moments while simultaneously questioning why she so unlovable. Dick move. Even if it’s tied with a bow, it’s still a dick move.

Image via YouTube

Email this to a friend

Kendra Syrdal

Once in college John Cusack asked Kendra to sing for him. She said no. Visit her website to ogle at her face and send hate mail //

32 Comments You must log in to comment, or create an account

Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More