All the Chaotic Gay Questions I’ve Asked on a First Date

I’ve always been deep, emotional, moody, and existential. As an Aquarius-Virgo-Virgo, I’ve found comfort in the ebb and flow of casual dating while simultaneously over-analyzing every conversation, text, photo, and gesture my potential partner is making. My innately chaotic dating energy has molded me into the incredibly knowledgeable top-notch Perfect First Date Professional I am today.

It’s all about the questions that spark and carry the conversation. Most of my first experiences in adult dating were with women, so my go-to questions were expected, if not already asked by the person I was seeing. As I started recently dating men again, I was thrown into a culture shock of just how gay queer dating is. The following are very real examples of questions on first dates, most of them asked without much context. While some of these first dates spurred from an actual friendship (so, a more acceptable scenario to ask unhinged questions), most of these were under an app context where I literally did not know the person.

I wouldn’t recommend using these unless you want to become someone’s therapist or completely scare them away.

What is your relationship like with your mom? 

Because who doesn’t want to get asked about their mom on a first date?

In all seriousness, I’m not sure if there’s a safe answer to this. The people who are extremely close to their moms have certainly been an issue, and the people who hate their moms have certainly been as issue. Correlation isn’t causation, but mommy issues are a real and scientific phenomenon.

Where do you see yourself in 10 years?

To which I say to myself “bro, what the actual fuck were you thinking.” The wildest part of this question is that I actually do have a 10 year plan. It’s not some crazy mapped out month-by-month agenda, but it’s the idea that in 10 years I want to be in X place doing X thing with X person.

Do you have color-changing LED light bulbs and/or light strips? 

I gotta be honest, every single person I’ve dated with some combination of these had been a walking red flag, and it always starts with them showing them off. LED lights aren’t a thing that just exist. You will know. They will tell you.

Picture yourself on your death bed. Now complete the phrase: “I’m so glad I ________.” 

This isn’t even a product of dark humor. I genuinely think this gives you a window into what motivates someone.

Would you want to do the New York Times 36 Questions to Love with me?

Of course I didn’t suggest we should fall in love on the first date. However, I will say that I fully did this with a first date once, and it ended in us kissing on a bench in a park so…how crazy is it actually?

How many times do you masturbate a day? 

I distinctly remember asking my first girlfriend this on our first date, fully in public drinking tea on a random Tuesday evening.

Picture yourself at a family holiday gathering (i.e. Thanksgiving dinner) and an argument unfolds between two people you love. What’s you role in this, if any at all? 

I guess I was thinking this would be a good question to weed out people who aren’t capable of conflict resolution? But that isn’t totally fair considering I become a ghost every time I’m at a family holiday gathering.

Do you have more top or bottom energy? 

This seems like a harmless question, but apparently cismen are floored by it.

Do you have nightstands on either side of your bed?

Listen, I have a whole theory on this one. Birthed from a combination of feng shui and manifesting culture, I believe the room you create is a reflection of what you’d like from life. If the person has a bed that’s centered between two nightstands (or a nightstand-desk combination), it means they are ready and willing to make room for two people and not just themselves. I kid you not — it’s the first thing I look for when someone invites me over. The fact that it’s a green flag for me is a red flag for those trying to date me. You’ve been warned.

How many friends do you have? 

A better way of asking this is “what does your support system look like?” but that’s too therapist-y for me.

What are your goals for the end of the year? 

If you’re a driven, ambitious workaholic, I suppose this isn’t an off-the-wall question. However, most of the people I’ve been on dates with give me a deer-in-headlights look when I ask this. Aren’t we all just trying to make is through the day? Yeah, me too, so why tf I am asking this question?

What did you dream about last night? 

With the caveat that if they don’t remember their dream, it’s a beige flag. There’s a reason people called me the Dream Interpreter in high school. Don’t make the mistake of letting me know your subconscious thoughts.

Vibe check: How are you feeling about me?

Bold of me to assume they would give me an honest answer to this — let alone a positive, honest answer. The more I read this, the more horribly narcissistic I sound. In my own defense, I’ll usually share a polished version of how I feel about them. The difference is that I’ve been assessing for that question the whole time, and they certainly haven’t.

Sorry if this feels like an interview. 

Not a question — more like a prompt to let me know how gay the person actually is.

Most of the people I asked these questions to aren’t in my life anymore, if that’s any indication of how things went.

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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she's not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em has written 71 articles for us.


  1. This is endearing, hilarious and scary all at once.
    As an Aquarian sun Virgo rising I thoroughly approve. My Moon in Cancer though, would no doubt become very still and look for the nearest exit LOL.

  2. “Picture yourself on your death bed. Now complete the phrase: ‘I’m so glad I ________.’”

    Yes! I volunteer for hospice and am fond of how clear people are near the end about what they’re proud of and what they care about. It’s made me want to pay more attention to those things in my own life.

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