First Message Faux Pas | What Not to Say in Your Opening Line

send first message

Look, online dating is not easy for 97% of the single population (that 3% are magical dating unicorns or just super hot). Shooting your shot on dating apps can feel like you are walking through a minefield in those huge clown shoes.

You want to stand out from everyone else, but you’re just one little (or big, remember, you are wearing oversized Bozo shoes) wrong-footed step away from a faux pas that blows up your chances of love (or at least a decent convo).

You have to know your audience and tread carefully—an opening message on a dating app is your first impression, your “nice to meet you,” and your eye contact rolled into one or two lines. That’s not an insane amount of pressure or anything! It’s only your love life at stake.

That’s why we are going to go over the dos and don’ts for sending that all-important first message, steering clear of the usual no-nos, and setting you up for success—and, hopefully, a great love connection!

The Don’ts: Classic Mistakes to Avoid

Your opener is your first—and only— impression on dating apps. Stay well clear from these more-common-than-you-think blunders to make sure you don’t step in it (you know what “it” is) and blow a potential connection!

red text bubble

The Generic “Hey”

Please, we beg of you, do not send a “Hey” or a “Hi.” It’s not offensive in any way, but it is boring as heck and done to death. It’s the online version of showing up to a black-tie wedding in PJs— incredibly underwhelming. It screams, “I showed up but put absolutely zero thought or effort into this.” And unless you are a firefighter and your profile picture is of you saving a bunch of puppies from a burning building, chances are pretty good a mere “hey” is just not gonna cut it.

red cloud text bubble

The Saga

Have you read War and Peace? If you did, it was probably because you had to read it for school, so you certainly don’t want to send a potential match a whole novel in an opening message. This is a dating app, not your autobiography, so don’t overwhelm them with a super long message—unless your life story is really interesting, no one’s gonna read all that. You might get a response, but it will probably be a TLDR meme. Or you could catch a block. 

red rectangle text bubble

The Creepy Comment

Commenting or even complimenting someone’s looks right from the jump will come across as superficial or creepy, depending on the person. There’s a very fine line between “I find you attractive” and “I’m only messaging you because you’re attractive.”

red oval text bubble

The Copy-Paste

Everything is online, and everything is copy, as the great Nora Ephron once said. And since this is the age of the internet, people can suss out a copy-paste job from 500 paces. You know those openers we are talking about—they’re usually Michael Scott quotes from The Office. It comes across as impersonal and really lazy. Yes, writing messages from scratch takes more time, but isn’t finding a compatible connection worth it?

red long text bubble

The Interrogator

Don’t bombard them with a ton of questions like you’re a police interrogator. People already have jobs and don’t want to feel like they’re on an interview to be your date, and asking too many questions, especially personal ones, is an interrogation, not a give-and-take conversation. Keep it light—you’re not vetting them for a position with the CIA, and this is a huge turn-off.

The Dos: Tips for Crafting the Perfect First Message

Now that you know what not to do, use these next tips to write an opening message that’s fun, genuine, and likely to get a positive or at least some kind of response. In a world of “heys,” be different. Don’t be that “sup” person!

green text bubble

Show You’ve Actually Read Their Dating Profile

A great first move is to demonstrate that you’ve read their dating profile! Sounds simple, right? It is! Pick out a detail you found interesting and comment on it. It could be a common interest, a niche hobby, or even a question about a photo they’ve posted. This opener shows that you’re interested in them as a person, not just another pretty face.

green cloud text bubble

Be Original

Instead of the overused “What’s up?” try something fresh. You can opt for a playful challenge like, “I bet I can make you laugh with my worst dad joke. Ready for it?” Originality grabs attention and sets you apart from the “How are you’s” that are already sitting in their inbox, likely being ignored.

green rectangle text bubble

Keep It Light and Upbeat

A first message should always be light, breezy, and casual. Keep the tone fun, upbeat, and inviting. A good rule of thumb is to write a message that you’d want to get from someone else—if you wouldn’t respond to it, don’t send it.

green oval text bubble

Ask Open-Ended Questions

Asking open-ended questions is a good way to start a convo—they require more than a simple yes or no answer. You could ask something like, “I saw your picture of you at a concert. What was the best live concert you’ve ever been to?” This not only shows interest in their interests but it allows them to share what they love.

green long text bubble

Got Humor? Use It

If you are funny, have a ton of wit, and humor is your thing, never be afraid to use it—you’d be a fool not to! A witty remark or a funny observation is a great icebreaker and makes your message more memorable than others. Just be sure it’s the kind of humor that’s not mean-spirited or punches down. Although some people like these kinds of jokes, not everyone does, so just assume they won’t go over well. Again, you could catch a block for a joke someone finds offensive or unkind.


The truth is, there’s no perfect formula for a fail-proof opening message—what works for one person could fall flat with another. Unless you are in that 3% category we talked about at the beginning, they don’t need a magic wand; people are just drawn to them. The most important thing is to be yourself, show genuine interest in the other person, and remember that, at the end of the day, everyone on dating apps is looking for the same thing—some kind of a romantic connection.

So, crack those knuckles, put on your thinking cap, type out that message, and hit send. Who knows? It could just be the beginning of something great.

And remember, online dating is full of ups and downs. Even with awkward first message mishaps, there’s a chance for a great conversation, a laugh, or even a first date!

Molly Davis
Molly Davis

Molly is an East Coast writer who lives on West Coast time. She’s been in the journalism field for over 20 years — newspapers are her first love but she’s finding digital media to be just as fun and challenging as print! When she’s not giving therapist-quality dating advice, she’s curled up watching movies, reading, or volunteering at local dog shelters.