Okay, so Halloween was coming up, and I thought, why not have a little fun with the texting game? Felt like trying out some themed flirty messages, just to see what happens, you know? Nothing too serious, just playful stuff.

Getting Started – The Idea Phase
First thing I did was just sit down and think about Halloween stuff. Pumpkins, ghosts, costumes, candy, spooky things… the usual suspects. Then I tried to mash those ideas up with something a little cheeky or complimentary. Didn’t want to go overboard, just something to make someone smile, maybe raise an eyebrow a little.
I scribbled down a few ideas. Some were pretty dumb, honestly. Like, really cheesy. I tossed those out pretty quick. Tried to aim for stuff that felt a bit more natural, even if it was themed.
Crafting the Texts
So, I settled on a few potentials. Here’s the kind of thing I was working with:
- Something about costumes: I thought about saying something like, “Can’t wait to see your costume… hope it’s scary good. 😉” Seemed okay, kinda standard.
- Playing with the ‘ghost’ theme: Maybe something like, “Are you dressing up as a ghost? Because you’ve been haunting my thoughts.” A bit cliché, maybe, but Halloween clichés are expected, right?
- Candy related: Everyone likes candy. So I thought, “Forget trick-or-treating, you’re the only treat I’m interested in tonight. 🎃” Felt a little bolder.
- A simpler one: Sometimes less is more. Just a “Hope you have a spook-tacular Halloween! Thinking of you.” could work too, less direct but still nice.
I picked a couple that felt right for the person I was texting. Didn’t want to send something super forward to someone I barely knew, obviously. Gotta gauge the situation.
Sending Them Out
Alright, then came the sending part. Picked one or two people I felt comfortable joking around with. Typed out the message, double-checked it so I didn’t make some weird typo, took a breath, and hit send. Yeah, felt a little bit silly, maybe a tiny bit nervous, wondering if they’d think it was lame or funny.

The Results & What I Found
So, what happened? Well, it was mixed, honestly. Which is kinda what I expected.
One person replied with a laughing emoji and played along, which was cool. We had a little back-and-forth banter. That one landed well.
Another reply was more like, “Haha, you too!” – friendly, but didn’t really bite on the flirty part. Which is also totally fine! No harm done.
Didn’t get any negative reactions, mostly just amusement or simple acknowledgement. It wasn’t like some magic trick that suddenly sparked fireworks, you know? It was just texting.
Final Thoughts
Overall, it was kind of fun. A low-stakes way to be a bit playful around the holiday. Didn’t take much effort, just a bit of thought. Would I do it again? Yeah, probably. It’s just another way to connect, break the ice, or share a little chuckle during a specific time of year.

The main thing I figured is, it works best if you already have a bit of a rapport with the person. And don’t expect miracles. It’s just a text message, after all. Keep it light, keep it appropriate for who you’re sending it to, and don’t stress too much about the outcome. It’s mostly just for a bit of Halloween fun.