The Six Questions You Should Ask On A First Date

Sometimes it’s hard to get right to the point on a first date. There aren’t many graceful ways to ask “So, exactly how crazy is your mom?”

While technology has made it easier to find an opportunity to go on dates, the fundamentals of getting to know someone can still be a struggle.

As Semi-Adults, we have to navigate dating while some of our friends are getting married and buying houses, and other friends are just trying to keep their house plants alive after they drunkenly watered them with citrus flavored Burnett’s…


Everyone is entitled to their own style of dating, but even if you’re dating without expectations, wouldn’t it be nice to know the red flags from date #1?

Time to be honest: Stop asking your date what their favorite color is. Don’t spend the whole first date debating if Q’doba or Chipotle is better. Serial killers and womanizers have favorite colors too. So let’s ask some questions that actually tell you what you’re getting yourself into, shall we?

1. If you won $1 million in the lottery, how would you spend it?

Disguising itself as a fun ice breaker question, you can actually learn a lot about someone by how they spend their money. Would they travel? Buy a fancy car? Pay off their debt? Distribute it between their family? It’s a sneaky way of figuring out what someone values, which is a pretty important topic in a successful relationship.

Warning: if he says something like “buy you a private island”

….pls just go ahead and sneak out the bathroom window.

2. If you could be a contestant on any game show, which game show would you choose?

Bachelor/Bachelorette: Probably not something you want to admit on the first date…

American Ninja Warrior: They are probably reeeeeeeeal competitive.

A cooking show: They love to cook? What a coincidence: I bet you love to eat.

Jeopardy: They must be really smart!

…or think they’re really smart!!

Ellen Game of Games: They don’t mind laughing at themselves, or could be big pranksters themselves.

Survivor: Psychopath.

3. Are you a morning or night person?

Honestly, ya gotta just cut to the chase with this one. If their idea of a fun Saturday is getting up at 5 AM to exercise or run errands while you’d rather sleep until noon because you watched scary movies until 3 AM the night before, ya might run into some issues.

4. As a dare, would you rather prank call your mom and tell her you were arrested, or tell her you were fired from your job?

Answering the question everybody would like to know from the start: “How crazy is your mom?” Depending on the answer, this question also has the potential to give you some insight on if they would rather worry or disappoint their mom.

For the love of all things good and holy, do some social media research before you ask this question. If they reply with “My mom is actually lost at sea…” just go ahead and chalk that up as an L.

5. If you could delete one holiday, which one would you choose?/If you could add one holiday (that you don’t already celebrate) to your calendar, which one would you choose?

Some families revolve their entire year around the holidays they celebrate. This question might clue you into:

  • How much family-time they are willing to tolerate?
  • Are they aware of/open to learning about other cultures?
  • Do they have to travel a lot to see their family during the year?
  • Do they have a cultural background that you didn’t know about?
  • Are they in a cult you should know about? *important*

6. What movie could you never get sick of?

Chances are, if this date escalates into something long term, you will probably get stuck watching this movie too. So you might want to make sure you can handle watching it once a month before you get too invested.

Life hack: This is a great way to figure out their go-to movie genre to avoid the inevitable “idk what do you wanna watch? Up to you.” battle.

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