8 Examples of Inappropriate Flirting — And How to Avoid It (Without Becoming a Robot or a Lawsuit)
Wednesday, April 16, 2025. This is for Mandy in Belgium, because she just asked.
What Even Is Inappropriate Flirting?
Let’s be clear upfront: flirting, in and of itself, is not a crime.
It’s a dance, a glance, a linguistic wink.
It’s been with us since people figured out how to lock eyes across a firepit. But inappropriate flirting?
That’s something different. That’s when the dance turns into a stomp, the glance into a leer, and the wink into an HR complaint.
Unappropriated flirting isn’t just about bad timing or awkward delivery.
It’s about ignoring context, consent, or common sense. It’s when one person thinks they’re being charming—and the other person’s nervous system hits the eject button.
So let’s walk through eight modern examples, complete with breakdowns of why they miss the mark and how to avoid stepping on social rakes with your flirty stiletto heels.
The Compliment That’s Actually Just a Body Scan
“You have the kind of legs that make a man rethink his marriage.”
Why It’s Inappropriate:
This isn’t a compliment; it’s a full-body TSA scan wrapped in a threat to someone else’s monogamy. It’s invasive, objectifying, and weirdly aggressive.
How to Avoid It:
Stick to compliments you could say on a name tag: “You’re thoughtful,” “That’s a clever idea,” “You’ve got great taste in books.” Keep your gaze—and your subtext—above the waistline and below the creepometer.
The Workplace Whisperer
“If you weren’t my coworker, I’d ask you out.”
Why It’s Inappropriate:
This move pretends to respect boundaries while actually trampling them with both feet. It’s a way to flirt and claim innocence, which is manipulative and cowardly.
How to Avoid It:
Flirting at work is like lighting a candle in a fireworks warehouse. If you're serious, wait until one of you has moved on professionally. Until then, keep it platonic and respectful. Admire their spreadsheet skills. Not their lips.
The Therapist Fantasy Dump
“I feel like we have a deep emotional connection. You just get me.”
Why It’s Inappropriate:
Ah yes, the weaponized vulnerability approach. This is especially common with people confusing emotional intimacy for sexual chemistry. Bonus demerits if you're saying this to someone in a caregiving or service role (bartender, nurse, literal therapist).
How to Avoid It:
If someone has to empathize with you because it’s their job, that’s not chemistry—it’s probably an effort to close a transaction. Wait to build reciprocal, voluntary emotional connections before tossing out soulful declarations.
The Persistent Re-Approacher
“You said you weren’t interested, but I just had to try again. And again. And again.”
Why It’s Inappropriate:
Romantic comedies have lied to you. “No” isn’t a narrative arc.
It’s a boundary. Pushing past it doesn’t make you romantic—it makes you off-putting and exhausting.
How to Avoid It:
If you’re flirting and they’re not flirting back, take the L with dignity.
You’re not a failure. You’re just not their flavor. Move on before you become a case study in someone’s therapy session.
The Double-Entendre Avalanche
“Well, I do like things that are long and hard… like crossword puzzles, of course.”
Why It’s Inappropriate:
This is less flirting and more stand-up comedy at a bachelor party no one asked for. Constant innuendo doesn’t create sexual tension; it creates awkward eye contact and hasty exits.
How to Avoid It:
Wit is wonderful. Wordplay is fine. But if your every interaction sounds like you’re auditioning to be the fifth guy fired from The Office, it’s time to recalibrate.
The Confessional Outpouring (on First Contact)
“I’ve just always felt so unloved. I’m probably too much. Sorry. I’m bad at this. Want to get coffee?”
Why It’s Inappropriate:
This is trauma-dumping disguised as flirting. You’re not building a connection—you’re recruiting a therapist with benefits. This kind of oversharing is intimacy on fast-forward and makes others feel like emotional hostages.
How to Avoid It:
Start light. Save the existential dread for date six. Or your actual therapist. Connection builds through small acts of presence, not emotional grenades.
The Touchy Feeler
A casual back rub. A shoulder squeeze. A “friendly” hand on the knee.
Why It’s Inappropriate:
Unwanted physical contact is a classic misfire. It assumes consent where there is none and places the burden of discomfort on the recipient.
How to Avoid It:
Unless you’re reading palms at a psychic convention or dancing salsa at a consent workshop, hands off. Ask first. Respect personal space. It’s hot when someone doesn’t feel like they need to flinch.
The “It’s Just a Joke” Gambit
“Wow, you look dangerous in that dress. Kidding! Kidding. Unless…”
Why It’s Inappropriate:
This is a manipulation technique that flirts while providing a built-in escape hatch. It’s plausible deniability wrapped in faux humor. It doesn’t charm; it erodes trust.
How to Avoid It:
Flirting isn’t poker. Don’t bluff. If you like someone, be kind, respectful, and just a little bit brave. And leave the sarcasm to retired English majors and Reddit threads.
The Difference Between Charm and Harm
Inappropriate flirting isn’t about attraction gone wrong—it’s about ignoring signals, structures, and power dynamics.
It thrives on one-sidedness. It turns curiosity into discomfort.
It forgets that all good flirting is mutual, invited, and a little playful.
Flirt like a decent human being. Not like a deleted scene from Mad Men.
Be Well, Stay Kind, and Godspeed.
REFERENCES
Abbey, A. (1987). Misperceptions of friendly behavior in naturally occurring cross-sex interactions. Journal of Nonverbal Behavior, 11(2), 120–128. https://doi.org/10.1007/BF00987029
Hall, J. A., Carter, S., Cody, M. J., & Albright, J. M. (2010). Individual differences in the communication of romantic interest: Development of the flirtation styles questionnaire. Communication Quarterly, 58(4), 365–393. https://doi.org/10.1080/01463373.2010.524875
O’Connor, M., & Segrin, C. (2015). Inappropriate sexual behavior at work: An exploration of personality and workplace variables. Journal of Interpersonal Violence, 30(5), 788–807. https://doi.org/10.1177/0886260514536273
Quinn-Nilas, C., et al. (2021). Consent is sexy: Associations between sexual consent, communication, and satisfaction. The Canadian Journal of Human Sexuality, 30(2), 143–152. https://doi.org/10.3138/cjhs.2020-0031