Buckle up because I’ve been in the online dating game off and on for a while, and trust me when I say, I’ve encountered some characters.

Here are six of the most memorable (and yes, ridiculous) ways guys have tried to flirt with me. As a word of caution, there are plenty of WTF moments.

1. The “finger” guy

Okay, so I have a total of four tattoos. Pretty standard, right? I mention it in my profile as one of the prompts, nothing crazy.

This guy slides into my messages and without missing a beat goes, “Well, I have five fingers… “ 😳 WHAT. IN. THE. WORLD.

This was the first ever conversation with this man, the one you’re supposed to impress. Where’s he going with this?

Of course, girls being girls, we have a whole armada of lovely friends to pick up flirting for us. My witty bestie took it upon herself to see this through on my behalf. She texted him, “What are you going to do with those five fingers?”

“I’d love to run them down your back” was his response. Is this supposed to be sexy? Because all I could picture was a crab claw creeping up my spine. Who thinks this works?! I couldn’t even respond; I was too busy trying to shake off the ick.

If I don’t even know your name and all I have is a possibly fake picture of you, please hold off on sexual innuendos ‘till later.

2. Mr. “What’s Your Deal?”

Ah, the direct approach. One dude opened up with, “What’s your deal?” Just… no context. No hello. Just straight-up interrogation mode like he’s trying to solve some mystery.

I mean, points for not wasting time, but bro, maybe ease into it? It felt like I was being interviewed for a crime show, and I wasn’t even the suspect.

He came at me like I owed him some sort of explanation for even existing on the app. His first message? Not “Hey” or “How’s it going?” No, my guy jumps straight to: “What’s your deal?” 🕵️‍♂️

Sir, my deal is not to tolerate rude strangers. I don’t even remember what I said, but it was something snarky before I unmatched him real quick. Boy, bye.

3. The Guy Who Struck a Nerve

Now, this one… ugh. He starts out pretty normal, a smooth talker who’s funny and charming. We’re chatting, things seem fine, and then out of nowhere, he hits me with, “So, are you just scared of settling down, or what?”

Like… excuse me? 🤯

Did he just psychoanalyze me on a dating app? I swear I stared at my screen for a full minute, questioning all my life choices.

I don’t know if it was some armchair psychologist flex or if I just looked like a commitment phobe to him, but it left me spiraling.

Did I delete the app immediately after? Yes. Did I re-download it two weeks later? Also yes.

We all need a break sometimes, okay?

4. Captain Slow Text

We’ve all encountered this guy. Everyone’s met him at some point. The one who takes days to respond.

He sends a “hey” and you reply, thinking, okay, we’re doing this. But then—nothing. A whole week goes by, and he pops back up with a “What’s up?” Bro. BRO.

We’re not talking about “I’m busy with work” slow; I’m talking “Let me send you a ‘hey’ and follow up two weeks later with a ‘what’s up?’”

By the time he responds, I’ve been on other dates, had a mental breakdown, got over it, and planned a weekend trip. Like, why even bother?

And when I asked him if he was a slow texter, he said he liked to “keep things casual.” 🙄 Nah, son. Keeping it casual doesn’t mean keeping it comatose.

5. The Endless Meme Guy

Don’t get me wrong—I love a good meme. Who doesn’t? But this guy was next level. I’m talking meme after meme with zero actual conversation.

It was like communicating with a Reddit bot on auto-loop.

At first, it was funny—like, ha-ha, good one—but by the 10th meme, I had to ask myself, “Is this it? Is this what dating is now? Just sending GIFs and hoping for the best?”

I had to tap out when he sent the Spongebob “Ight, Imma Head Out” meme… like, dude, me too. 😂

6. The “How Long Have You Been Single?” Guy

Oh man, this one gets me every time. So I’ve had multiple guys ask me this, but it still blows my mind.

“How long have you been single?” Like, am I giving off single forever vibes here?

What is this question supposed to achieve? Do you want to compare our loneliness timelines? Is this a subtle dig to remind me of how tragic my dating life is?

One dude asked this, and when I told him how long, he followed up with, “Oh, I can see why.”

EXCUSE ME?!

I couldn’t hit that block button fast enough. Like, what did he expect? Applause for his rudeness?

So yeah, online dating. Sometimes it’s gold, and other times it’s just a guy offering to run his fingers down your back. The struggle is real!