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People Tell Us About the Weird Things They Ask on a First Date

There are some things a person just needs to know.
Photo via Flickr user Wyatt Fisher take two

First dates suck. OK, It feels like I haven't been on an actual date since the beginning of high school, but I still know that dating, and especially first dates, can be awkward at best.

First dates can feel like all you're trying to do is ask the right questions while not coming across as overly invasive. There's the basic stuff like, "Are you vegan?" "Are you a murderer/undercover clown?," "Do you have a job?" and "How many people are you lowkey dating?"


But what about the questions you really need answers to, especially before a hookup, like, "How often do you wash your bed sheets?"; "Do you use plastic or reusable grocery bags?"; "Anything weird going on in your pants that I should know about?"; "Why are you putting on a clown mask?"

From what I can tell, dating is about asking all the right questions so I surveyed some people on what they ask strangers on a first date or before a hookup.

*Carly, 27

Is there anything you have to ask on a first or before a hook up?
I like asking guys how they feel about sex workers and strip clubs. It's funny to watch them lie, and it shows if they're jerks who slut shame women.

Once I went on a first date on Valentine's Day, and the guy was a photographer. He told me that he dreamed of taking photos of the lockers in the dressing rooms of strip clubs because he heard they're covered in Disney stickers because those women didn't have childhoods. It was revolting and ignorant, and we never spoke again.

How do most guys respond to those questions?
Sometimes I get them being like, "Gross no I hate strip clubs, that's disgusting." That's the worst answer. Maybe they're lying because they think I want them to say that, I'm not sure. But I don't like that attitude regardless so it's a red flag.

A lot of guys are honest, I think. Finance guys go to strip clubs a lot so it's commonplace. Guys from Montreal have gone since they were like 17 so they don't get too excited about this topic either. Suburban Toronto guys have the most awkward replies, in my experience.


And sometimes they'll get really honest and say "I saw a sex worker once, in Thailand. Or something like that." In that case, it usually comes out much later in the relationship. I love that though. I think every guy should support his local sex workers.

Why is asking that question important to you?
Sex worker rights are important to me. But beyond a social justice angle, it says a lot about how a guy is going to express himself sexually—is he adventurous? Is he honest about what he likes? Is he respectful of women who are sexually exploratory?

In one way or another, we should all support sex workers —that doesn't mean paying them for sex, but it does mean speaking respectfully about them, seeing their work as legitimate and supporting their human rights and labour rights… In my opinion, the kind of guy who says strippers aren't fun and hot is the kind of guy who will cheat on you with your neighbour three years down the road. Every woman should ask this question.

Also, I am a sex worker. When dating you want to know you're with someone who is thoughtful and kind and those kinds of people don't judge and hate sex workers.

Here are vegetables shaped like a dicks. Photo by the author

Dianya, 21

So what's something you always ask on a first date or before a hookup?
I always ask guys to walk my dog before I bring them back to my place. And I ask them what kind of vegetable they would be if they could be any vegetable.

Why do you ask about what vegetable they would be?
It's an easy icebreaker.


And why do you ask them to walk your dog?
My dog is impossible to walk so it gives me an extra 15 minutes to talk to them and decide if they're chill before I bring them or don't bring them to my place.

Why do you ask about vegetables specifically?
Because it's weird. If they can't roll with it then I don't wanna smooch.

What's the response you usually get?
Everyone actually humours me and they'll pick a vegetable. This guy I met last night said he'd be a ghost pepper. And the response has to be based on what vegetable you feel like inside, not what you like to eat. Although too many guys have just said cucumber because it's wiener shaped which is pretty lame.

Is that also how you decide if you want to hook up with them or not, based on what vegetable they choose?
Oh ya.

Ya, all feet are pretty disgusting. Photo by the author

Kate, 19

Let's say you're on a first date or you want to hook up with someone, is there anything you have to ask them right away?
I need to know if they have fucked up feet. My current boyfriend has a lot of health issues, and one of them is with his feet. On our first date I was sad to hear that he can't go into the water or walk barefoot anywhere because he has fucked up feet.

Thankfully he's more than his feet, but it sucked not being able to go swim with him.

What's wrong exactly with his feet?
He got nail fungus from a gym shower before we met. Poor guy hasn't been able to swim through his 20s. And he's got a wart in his heel, and when you get warts in your heels they grow upwards and are impossible to dig out.


Every time I sleep over I watch him clean his feet up and occasionally push the fungus filled toenails off. I feel so bad because it hurts him… He's a super hygiene freak, which is why I never really asked when we first met.

So that's something you would usually ask? If they have fucked up feet?
Ya definitely because your feet are a reflection of who you are 90 percent of the time. If you don't cut your damn toenails I can't go out with you or sleep with you. That's the rule. I don't want to get scratched by toenails. Dudes can be very careless with their feet.

So you think someone's feet are a reflection of their personality?
Definitely. Hygiene is a reflection of who you are and feet are a huge part of it.

Have you dealt with foot issues before your current boyfriend?
Ya, I have. I've smelt some smelly feet; people who don't believe in socks. When I was more sexually adventurous, I hooked up with this one guy who actually scratched me with his toenail. The big one. It fucking hurt. That's when my severe hatred for unkempt feet really started.

I'm pretty good at predicting whether or not people have weird feet on my own, but I ask. How do you tell if someone has nice or ugly feet?
Their overall appearance, their hands and their hair. Also with how they dress. People who put effort into their outfits don't skip out on anything.

Wendy, 34

Is there anything you have to ask on a first date or before a hook up?
I ask if they have any certain fetishes.

Why do you ask that?
I've been on some great dates but by the third date they tell me they want to pee on me or put me in a cage so after that happened a dozen times it was something I asked about ahead of time. I didn't want anymore surprises. It's also to see their reaction.


People said they wanted to put you in a cage and pee on you?
I've had all sorts of strange requests. It may be because I don't really judge people. The first few dates would be cool but then out of nowhere there would be random requests to do sexual things.

I never really cared but it wasn't my cup of tea. Golden showers are more common than you would think. The cage thing happened once and then there would be requests to have threesomes with me… Those requests usually started with them being like, "I'd like to try anal beads, or something like that in myself and maybe have a dude join us."

And what would you do?
Usually there would be nervous laughter, followed by me being like, "Haha funny." But then realizing they're not joking. I'd say that I wasn't into that but that I wasn't judging them. If it's something they needed to explore, it would have to be with someone else.

Jennifer, 18

Let's say you're about to hook up with someone, is there anything you have to ask them first?
Because I'm severely allergic to peanuts, before I hook up with someone I have to ask them if they've eaten anything with nuts that day.

Have you had any bad experiences with your allergies?
One time I was about to hook up with this guy who I was friends with benefits with at the time, and I asked him if he ate anything with nuts that day. He said no, so we did our thing. I went home and started having a reaction.

And then what?
I ended up in the emergency room at the hospital.

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