From doodling on sticky notes to texting (meh, but can’t be hypocritical) your prospect after an overanalyzed list of pros and cons, to some extravagant proposal planned in Parker Hall – we’ve all seen the spectrum of asking someone-out strategies. 

Some like grand proposals straight out of the first half of La La Land, while others are just as happy catching a low-key indie film vibe in MC Aud. Then there are the artsy types who create a Victorian puzzle with secret compartments to hint at the question. For some, it’s just about being honest and keeping things relaxed. After all, there’s no one-size-fits-all approach to asking someone out–the possibilities are as wild or simple as you make them.

Dos (Because Nobody Wants Their Ask-Out to Be the Next School-Wide Meme):

 “Keep it genuine and relaxed; it’s not an audition for a hallmark rom-com.”

  1. Be personal and thoughtful (keep it genuine): Forget the cheesy lines (or don’t if they like it)–what makes this person stand out to you? Show that you’ve been paying attention. Remember their weird obsession with Clairo or their love for How to Train Your Dragon marathons. Make the ask-out about them, and not you. Being thoughtful isn’t about grand gestures; it’s about showing you care enough to notice the little things.
  1. Be direct (but chill): Sometimes, less is more. Just a simple “Hey, I like talking to you — want to grab a coffee sometime?” works way better than a dramatic speech or a sweaty panic moment. Keep it genuine and relaxed; it’s not an audition for a hallmark rom-com.
  1. Know their vibe: If they’re into comfortable, low-key vibes, keep it simple— a coffee at Tangerine or a walk to CFI. If they’re the life-of-the-party type, lean into something playful and fun, but never overdo it to the point of discomfort. The key is respecting their comfort zone.
  1. Show confidence (even if you’re nervous): Confidence isn’t about being perfect; it’s about showing that you genuinely care enough to ask and are sure about it. Uncertainty? It rarely wins anyone over.

Don’ts (Please Don’t Be That Person): 

“Acting too casually while pulling off a big, dramatic gesture? It usually backfires. “

  1. Don’t spit anxiously while talking: It’s a no for most people (anonymous sources)–and honestly, the prospect is dodging literal bullets. Pro tip: talk slowly, it stops the spitting and makes the conversation understandable. 
  1. Read the room: If they’re into quiet vibes, don’t sing “everybody loves somebody” in the dining hall. It should feel special to them. And if it’s a classmate, just make sure you’re not making things weird for them in the next group project.
  1. Don’t act nonchalant about it: Acting too casually while pulling off a big, dramatic gesture? It usually backfires. It’s like giving someone a bouquet and saying, “Whatever, it’s just flowers.” Keep it thoughtful and sincere, not a mind game.
  1. Don’t tell the entire grade before asking the person: No one wants to hear about your plans from someone before you even show up.
  1. Don’t text or (gasp) email on Outlook: “Yo wsg, wanna go jsb together?” it gives the ick and will be remembered for all the wrong reasons.
  1. Don’t pitch the backup plan: “I’ll go with you if [insert name here] says no.” Nope. Unforgivable.

Because We Love Tea (And Spilling It):

Now for the good stuff – some stories and solid advice straight from the pros (or so they claim).

Mr. Shrey said, “I didn’t ask someone out, unfortunately,” only for Ms. Priyanka to retort, “I knew you couldn’t.” Brutal but fair.

Then there’s Señor Antonio, who advises everyone to “just ask them out for a tangerine coffee date.” (He’d also like everyone to know that cinnamon lattes are his favourite — take note.)

Devashish proudly declared that he’s always ready to be asked out. Confidence goals, honestly.

Mr Will, who tends to know all the grade gossip, wants me to inform that he’s the best person for advice (if you want it to go horribly).

[This is fake news]

Whether you’re creating a playlist that captures all your inside jokes, staging a grand flash mob, or using the StuCo rose service as your messenger — the key is making it thoughtful and considerate. And hey, if it doesn’t pan out? At least you’ll have something to talk about during lunch.

Disclaimer: These opinions are from real people (not just me), don’t blame me if they say no. I’m just the messenger.

Narayani, Class of 2025, is co-editor of the Woodstocker