How to propose a boy on chat easily? Try these quick tips for success now!

So last Thursday I was texting this guy I’ve been crushing on for months. My hands were actually shaking holding the phone, no joke. Felt like some high school crap but whatever. Decided screw it, I’m gonna shoot my shot through chat ’cause face-to-face ain’t happening with my awkwardness.

The Freaking Preparation

First thing I did? Stalked his profile pics again. Needed to time this right. Saw he posted a gym selfie an hour ago – good sign he’s in decent mood. Also made sure I knew his schedule – dude always naps at 3pm so 11am felt safe. Didn’t wanna get left on read during nap time.

Wrote my opener five times. Seriously. Deleted stuff like:

How to propose a boy on chat easily? Try these quick tips for success now!

  • “Hey you might think this is weird but…” (sounds desperate)
  • “So hypothetically…” (too chicken)
  • Just a waving emoji (zero effort)

Ended up copying my friend’s advice:

“Saw that cool guitar pic you posted yesterday! Makes me wanna ask – wanna grab coffee sometime? I’ll bring terrible band recommendations 😂”

Sending The Damn Message

Hit send at 10:57am. Then panic mode. Immediately:

  • Tossed phone under couch cushion
  • Made burnt toast
  • Spilled orange juice cleaning said toast
  • Checked phone at 11:03 – NOTHING

My stomach dropped thinking I blew it. Then at 11:07…

DING.

Three typing bubbles show up. Felt like eternity. Then:

“HA your timing’s wild – just got dumped yesterday. But hell yeah coffee sounds better than my sad playlist rn 😂”

Chaos Mode Activated

Me being dumb thought this meant we’re trauma-bonding now. Replied:

“OMG that sucks!! Want me to come over with pizza? Emotional damage pizza is free tonight”

…Instantly realized how thirsty that sounded. Cue frantic damage control:

  • Sent crying-laughing emoji
  • Followed by “JK unless…?”
  • Then “Wait no bad joke”
  • Finally “Forget the pizza comment pls”

Saw him typing again. Held breath. Got:

“LMAO you’re wild. But honestly? I’ll take the pizza.”

So guess what happened?

We demolished two large pepperonis while binging trashy reality TV. Zero romance. But laughing hard enough I forgot about the original proposal. Made concrete plans for real coffee next Tuesday. Baby steps.

What Actually Worked

  • Used his interest as bait (that guitar pic)
  • Kept it casual (coffee > dinner)
  • Made him laugh (even at my expense)
  • Showed zero pressure (that burned toast was key)

It ain’t some romcom confession. But honestly? Better. Real. Plus got pizza out of it.

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