Article By Meredith Dietz
~ DECEMBER 2021 ~ Within every dating app’s direct messages is a delicate dance. You want to be forward without coming on too strong. You want to play it cool without losing someone’s interest. You want to be flirty without scaring someone off.
If you’re even remotely online, you’ve seen the screenshots of people botching this dance. There’s “teasing” that’s simply offensive, pick-up lines straight from 1995, and of course, “incel behavior.”
How can you message with your match without making the other person regret swiping right on you? Here are some common mistakes you might be making in the DMs, and what you can do instead to get sparks flying.
Giving one-word answers
You might think you’re coming across as mysterious, but in reality, you’re just being frustrating. While one-word answers can sometimes fly during face-to-face conversation, they’re essentially the same thing as punctuation over text. Even if someone asks you a yes-or-no question, you should be able to build off of that to keep the conversation flowing.
What to do instead: Elaborate in your replies in order to show interest in the other person (and to make yourself more interesting to them). If you’re feeling extra motivated, you could even (gasp) ask someone a question about themselves.
Asking way too personal questions
It’s important to ask questions in order to get your conversation off the ground, but be wary of getting too personal too quickly. For instance, asking someone “Do you have siblings?” is normal. Asking them, “How is your relationship with your father and what are you doing to repair it?” is…less normal. I know how nice it is to feel like you’re making a connection and finally moving beyond boring small talk, but save potentially invasive questions for down the line (and ideally face-to-face).
What to do instead: While you’re still communicating via in-app messages, steer clear of traditionally touchy areas like familial relationships, money, medical procedures, and so on.
Negging (instead of teasing)
Teasing is an art. Negging is manipulative. True negging is the use of low-grade insults in order to make someone more vulnerable to your advances. All too often people will “roast” someone in an effort to seem cool and funny, or as a way to rush into a certain level of familiarity. But when you’re in the DMs and don’t really know each other, your attempt at “roasting” might just be plain rude.
What to do instead: If you’re uncertain about how your teasing is being received, err on the side of caution. It will be easier to read the room in-person, but you won’t get that face-to-face opportunity if you offend them now.
Over-showering with compliments
Compliments are a no-brainer way to show you’re kind, personable, and flirtatious. If you go overboard, however, you risk coming across as insincere, desperate, and probably more than a tad creepy. This is the flip side of negging, where too many compliments assumes a level of intimacy or intensity that a dating app simply doesn’t warrant. At the end of the day, you can’t really know someone from a few DMs. At this stage, it’s better to ask questions to someone, rather than making comments about them (even compliments).
What to do instead: A compliment here and there is flirting 101; but if you can’t hold a conversation without weaving a compliment into every message, consider scaling it back. Put more simply: Don’t lay it on too thick.
Here I’m using “entitled” as a diplomatic way to describe “incel behavior.” I’ve gotten my fair share of messages from people (almost exclusively men) that are aggressive and arrogant in terms of what they expect from dating apps. Think messages like “What do I have to do to get a response on here?” and “Wow, guess I’m not good enough for you?” and “Classic female, ignoring a nice message from a guy like me.” These types of messages show that you don’t think of me as a fellow human, but as a receptacle built solely for you to process your own ego. In short, it’s not a great look.
What to do instead: Accept the realities of the modern world, in which 1. a majority of matches lead to nothing, 2. ghosting is common practice, and 3. no one owes you anything ever.
Taking yourself too seriously
A dating app profile is not a job interview. You can describe yourself as “honest,” and “entrepreneurial,” and “ambitious;” all I’ll be able to see is “boring,” “bland,” and “blegh.”
I think profiles that take themselves seriously are usually for people who are serious about finding a good match. When you are looking for something super casual, it’s best to communicate that right off the bat. However, the inverse is not necessarily true. If you’re looking for something serious, and you try to communicate that within the first message or two, you risk coming on way too strong.
What to do instead: Have a little fun! Build a rapport first, and then organically bring up the fact that you’re ideally looking for something more than a hookup. If you’re worried about wasting time, bring this up before the first date—but don’t let it be your pickup line.
Sending unrequested pics
Thank the powers that be that most apps won’t allow you to send unsolicited pictures through their direct messaging system. If you’re wondering whether or not you should send someone a photo that they didn’t directly ask you for, please allow me to remove all ambiguity from the equation.
What to do instead: Luckily, there’s an easy solution here. Never send pictures unprompted. Never! Whatever payoff you’re imagining is not going to be worth the risk.
Asking for someone’s number too soon
While it’s a good idea to schedule a real date within the first two weeks of messaging someone, don’t skip the very important rapport-building stage. An attempt to be confident can quickly turn into presumptuous.
What to do instead: Before asking for someone’s number (or giving out your own unprompted), make sure that you both have established common interest in each other. And please, never call someone out of the blue. It’s 2021. Not even my mom calls me out of the blue.
Using impersonal pickup lines
“Well, here I am. What are your other two wishes?” Don’t get me wrong, I smile when I get an extra cheesy opening line. Unfortunately, that doesn’t always mean I’ll actually engage past that. Like with cover letters, it’s obvious when you’re shooting your shot with the same lines over and over.
What to do instead: Specificity is your friend. You can still be corny with a line that comes directly from something specific to your match’s profile. Here’s a hack from dating coach Logan Ury, director of Relationship Science at Hinge, and one of our guests on Lifehacker’s podcast, The Upgrade: Use your opening line to comment on something on the bottom of their profile, since it’s probably less common that someone else has responded to that.
Like with the pitfalls of asking someone invasive questions about themselves, don’t cross boundaries by divulging too much about yourself. There’s a very real desire to speed up the small talk stage and get to the “deep stuff,” but that’s something you have to earn with time. Otherwise, you’re putting someone who is mostly a stranger into an uncomfortable position.
What to do instead: Some things are best saved for in-person conversations, or a few—or several—months into a relationship. Keep your emotions and boundaries in check by sticking to lighthearted subjects (TV, books, hobbies) over the heavy-hitters (past relationships, childhood trauma, medical histories).
Outwardly hating the apps
We get it: You hate dating apps. I hate dating apps. And yet here we both are. Anyone on Hinge who knows the prompt “The worst mistake I ever made…” also knows the type of profile that responds with “…downloading this app.” Believe me, I understand the shame, burn-out, and disappointment that comes from endless swiping. Still, it won’t work in your favor to act as if you’re too cool to be here. It’s an odd tactic to try and bring us both down for playing the love game in this specific arena.
What to do instead: Accept the fact that for better or for worse, we’re both giving dating apps a shot. Keep your bitterness to yourself and play the game.
Hating “small talk”
Yeah, nobody loves talking about the weather. However, what you’re thinking of as “small talk” might just be another person’s barometer for whether or not you’re a total creep. Whenever someone tells me they “hate small talk,” I usually roll my eyes and assume they think they’re not going to be a lot of fun.
What to do instead: Be patient with a certain level of rapport-building. Find a happy compromise between “What did you do today?” and “What do you think happens after we die?” Again, specificity is key. Think up some creative ice breakers to get around the dreaded small talk, e.g. asking about someone’s weirdest dreams, or what they’d want to eat for their final meal. Have fun with it.
Listing specific requirements
The thought of matching with you shouldn’t feel like applying to a job. I’ve never been attracted to someone who messages me to make sure I love cars, hate a certain sports team, and have seen every episode of The Sopranos.
What to do instead: Be open-minded. Even if you have an internal checklist for your perfect match, keep it to yourself. There’s a good chance you don’t even know what you really want in this world. And perhaps what you want isn’t what you actually need, you know?
Referencing The Office
This one breaks my heart, but The Office is dead. Yes, I was a die-hard fan when it originally aired. Then, when its popularity hit critical mass, I became a hater. And now we’ve come full circle where hating the show has–you guessed it–also hit critical mass. No matter your opinion on the show, bringing it up on the apps is a fast-track to eye-roll city.
What to do instead: Find another show to base your personality around. Arrested Development is next in line for being overly referenced, so get it in while you can.
Adding someone on LinkedIn
Finding someone’s Instagram or Twitter from a dating app is normal. Requesting to follow them is a risk (unless you’ve already been on a few dates). Finding someone on LinkedIn, which is more of a job hunting site than a social media platform, is a whole other story. Adding someone on LinkedIn is a wild leap from potential romance to business professionalism. Are you trying to go on a date or are you trying to further your career?
What to do instead: Don’t mix business with pleasure.
Having zero personality
At this point, you might feel backed into a corner with what you can and cannot do on the apps. Maybe you feel more confused than when we started. How can you stand out without coming on too strong? How can you be confident and direct without sending someone running in the other direction? What’s a single person to do?
Ultimately, you have to be yourself. Don’t let a fear of making a misstep stop you from shooting your shot. The trial-and-error of messaging your match is going to be worth more than sulking all alone (as long as you aren’t an arrogant, boundaries-crossing creep, of course). (I do not endorse being a creep.)
What to do instead: If you’re stressed about how you’re coming across on the apps, grab a friend to help you show off your personality. We’re not always the best at portraying ourselves accurately, so your friends might be able to fill in some gaps to make the profile seem more “you.” At the very least, good friends might just be able to give you the necessary ego boost so that you have the confidence to make the first move. For the most part, think of the dating apps game as low risk, high reward.