Dating App Etiquette | Michael Scott Edition


Are your dating app openers as cringeworthy as Michael Scott’s public speeches? If your go-to line is “Are you a parking ticket? Because you’ve got ‘fine’ written all over you,” then dating fam, we need to have a serious talk.

Is your go-to on dating apps not-so-hilarious bad pick-up lines, awkward first messages, or even pushing “love contracts” a little too early in the dating process? Well, don’t worry. Or maybe worry a little bit. 

But there’s hope for all of us, especially if we take a closer look at The Office’s Michael Scott’s notoriously awkward, bordering on offensive, romantic escapades as a roadmap to understand what *not* to do. So, strap yourself into an uncomfortable office chair as we go over some classic Michael Scott moments that illustrate the not-so-great ways of using dating apps—and how to counter the inner Michael Scott in all of us so you can meet your match and use them in an effective and respectful way!

michael scott icebreaker

The Infamous Ice Breakers

Remember the time Michael Scott said to his office crush, “You must be from Jamaica because Jamaican me crazy?” Oof. Starting a conversation with a cringe-worthy pick-up line that is inappropriate at best and offensive at worst is like applying for a job with a resume written in a red Sharpie marker.

Expert Dating Tip: Start conversations with something more personalized based on the person’s dating profile. This shows you’re genuinely interested and have taken the time to actually read their profile, not just gawk at their pic.


Michael scott too much too soon

Too Much, Way Too Soon

Michael once bought a ridiculously expensive neon beer sign for his would-be girlfriend Carol—on their second date. Similarly, disclosing your deepest fears, dreams, or the names of your future children before the first date is TMI! Take it down several notches and chill. 

Expert Dating Tip: Keep conversations light initially. You don’t want to scare someone off by making it too serious too quickly.

Michael Scott filter fail

Filter Fails

Can we ever forget Prison Mike? He thought using an alter-ego would make him seem more edgy and intimidating. On dating apps, this translates to using filters, Photoshop, or 10-year-old photos that look nothing like the real you.

Expert Dating Tip: Authenticity is key. Use recent, clear pics that show who you are, not who you think people want to see.

Michael Scott foot in mouth

The “Foot-in-Mouth” Syndrome

Remember when Michael compared Jan’s breast augmentation to getting a new computer? OMG, Michael! Saying inappropriate or offensive things is always easier behind a screen, but that doesn’t make it okay.

Expert Dating Tip: Be respectful and considerate. If you wouldn’t say it in person, don’t say it on a dating app.

michael scott jumping the gun

Jumping the Gun

Michael proposed to Carol in front of a Diwali celebration crowd after only a few dates. While you probably won’t be proposing, moving too fast, like suggesting a weekend getaway as a first date, is insane and will probably end up with your once promising potential match blocking you. 

Expert Dating Tip: Take things slow. Get to know the person well and interact for a good bit before taking any major leaps.

Michael Scott being too eager

Being Too Eager

Michael’s constant craving for approval and immediate responses is his downfall—it’s needy and plain unattractive. Similarly, bombarding your match with messages will only make you look desperate.

Expert Dating Tip: It’s important to gauge the flow of conversation and adjust your message frequency accordingly.

michael scott love contract

Hard No to a ‘Love Contract’

Remember the infamous love contract Michael tried to get Jan to sign? Of course, you do. In the dating app world, this will be equated to controlling, toxic behavior, so don’t try laying down any rules and expectations prematurely. You’re not the boss of anyone. 

Expert Dating Tip: Communication is important, but let the relationship develop naturally without imposing restrictions or ultimatums.

Michael scott token friend

The Token Friend Endorsement

Remember when Michael requested Dwight to speak on his behalf for his romantic interests? Unless you’re aiming for comedic value, avoid using friends to vouch for you on your dating profile. It’s weird, no thanks, swipe left. 

Expert Dating Tip: Let your own qualities speak for themselves. If someone is interested, they’ll be interested in you, not your wingman’s sales pitch.

Michael Scott Stalking

Stalking is NOT Romantic (It’s Legit a Crime)

At one point, Michael took following people to a new, concerning level. On dating apps, this could translate to social media stalking before even meeting the person. And remember, The Office is not real life, so while it may have been funny on the screen, it’s not IRL. 

Expert Dating Tip: Give people their space. Learn about them through conversation and shared experiences, not through a deep dive into their online life.

Michael Scott be you but better

Be You, But Better

Even with his flaws, Michael Scott is a lovable idiot because he is unapologetically himself (for better or worse). On dating apps, it’s tempting to portray an idealized version of yourself, but that can lead to mismatched expectations.

Expert Dating Tip: Be yourself, but also be your best self. Show kindness, respect, and genuine interest, and you’re sure to find a meaningful connection.

michael scott misleading job titles

Misleading Job Titles

Who can forget Michael Scott’s self-proclaimed title of “World’s Best Boss?” While this over-the-top designation is funny in a sitcom, inflating your job title or lying about your accomplishments on a dating profile is deceptive and is sure to disappoint your date. 

Expert Dating Tip: Honesty is the best policy. Whether you’re a “Regional Manager” or “Assistant to the Regional Manager,” be upfront. Authenticity creates genuine connections, and starting a relationship with a lie is never a good idea. It’s a bad one, and you’ll be found out or have to ‘fess up sooner or later. 

michael scott obsession with exes

Obsession with Exes

Michael’s infatuation with Jan long after their breakup serves as a cautionary tale. Constantly talking about your ex while trying to date someone new is a bright red flag.

Expert Dating Tip: Keep the past in the past. When using dating apps, focus on the possible future with a potential match rather than comparing them to people you’ve previously dated.


So, if you’re adrift in the tumultuous sea of dating apps, let Michael Scott be your lighthouse—or maybe your warning buoy. Either way, recognizing the error of his romantic buffoonery and learning from it, a “what not to do” manual can help you navigate your own romantic dalliances more successfully. 

Whether you’re a Michael Scott in the making or just someone looking to improve their dating app game, remember this: dating apps are only a tool, not a solution. Make real connections, and maybe you’ll find your own Holly Flax—without the cringe-worthy jokes and awkward moments (or maybe with, if that’s your thing).

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