Clever Ways to Start a Conversation on a Dating App (That Aren’t Creepy, Cheesy, or Boring)

After tweeting out a joke and a screenshot of someone messaging me on Hinge, I recently read through a lot of complaints (mostly from men) about how it feels like there are only two options when you reach out to someone on dating apps: Get ignored or get mocked.

While I understand the sentiment, I have to disagree with this dismal outlook. The “get ignored” or “get mocked” binary is a false one. There are plenty of options for the middle road. With a little bit of thought, you can start a conversation without sounding too boring, too cheesy, too cocky, or too creepy.

Many bloggers, myself included, have emphasised the need to personalise the messages you send on dating apps. The market is too competitive for the one-size-fits-all pick-up lines of yore. You need to actually respond to something specific in someone’s profile if you want to start a fruitful conversation.

With that in mind, what use is this article? If the advice always comes down to customising your message on a case-by-case basis, how can I help you? Tragically, I can’t grab your phone from your hands and do the swiping for you (not for free, at least).

Here’s the thing, though: We can anticipate a lot of what you’re going to encounter on someone’s dating profile. If your ability to judge what’s corny and what’s creepy is feeling off-base, let the following examples help you recalibrate.

Here are some thought-starters for surefire conversation starters on dating apps, organised around the sort of photos and prompts you can expect to find on many profiles.

If they have a concert pic…

A concert pic is usually a layup for starting a conversation. Perhaps where you’re going wrong is by swooping in with an observation instead of question. Instead of saying something bland like, “This looks fun,” try asking something open-ended, like, “What concert was this?” or “Got any concerts you’re looking forward to?” If you recognise the venue or musician, even better.

If they mention the number of countries they visited…

Travel pics are a dating profile staple. Your instinct might be to ask “Where was this photo taken?” but I encourage you to ask a more open-ended conversation-starter. As someone fairly well-travelled, I’d rather be asked about where I want to visit next over where I’ve already been. The “crazy travel story” prompt doesn’t translate that well over text, often ending in a one-sided “you had to be there” moment. Alternatively, “bucket lists” give you plenty of room for a fun, flirty back-and-forth.

If they have a pic with a fish and/or reference the trope of a pic with a fish…

The good ol’ “I caught a fish” pic. For this inevitability, a Twitter mutual messaged me the perfect way to stand out from all the other fish in the sea. In response to a profile prompt like, “If you’re holding a dead fish in your photos, I’m not interested,” you could respond, “I’m not holding a dead fish, but if you would like to hold something dead inside, we could cuddle.” It’s the perfect amount of weird to ensure you stand out.

If you want to compliment their looks…

We’re not all looking for a soulmate. Even if you’re swiping on someone simply because they’re hot, you can still be tactful and original about it. “Wow, you’re gorgeous,” sounds like you copy/pasted that to a hundred profiles before mine. Not only can physical compliments sound impersonal, they can also come across as real off-putting real quick.

Hit on hot people the same way you’d hit on someone for their personality. Revolutionary, I know. If they have a photo of them looking stunning on a sunny beach, play it coy and message them asking where they went on vacation. Focus on the beach, not the bod. You increase your chances of standing out if you can prove that their profile successfully interested you for less superficial reasons (even if you have superficial intentions).

If their profile made you laugh…

Tell them why. Not to brag, but I’ve gotten a few “you seem funny” DMs in my day. Unfortunately, my wit doesn’t know what to do with that other than say “thank you.” Use the initial compliment as a launching point for a bigger conversation starter. For example, “This response reminds me of [favourite comedian]” or “This is hilarious, I’d love to know what shows/movies are making you laugh right now.” Even if you’re grasping at straws, this approach at least gives the funny person something to work with.

Oh, and if you’re something a comedian yourself? Play along! Try to build off the jokes in their profile. Nothing says “love connection” like the ability to quote It’s Always Sunny back and forth.

If they have a niche meme…

The inclusion of a meme on someone’s dating profile is tricky territory. While it can be an efficient way to signal your sense of humour, it’s not always a productive conversation-starter. If there’s a “tag yourself” element involved, take that and run with it. Otherwise, I’d avoid the allure of the meme and respond to a different photo altogether. Or, take a more general “you made me laugh” approach, as described above.

If they say “sarcasm is my second language…”

Swipe left.

At the end of the day: Be the coolest version of yourself

You need to be yourself. Blah blah blah. The best way to be your best self is to master the art of “casual weird.” “Casual weird” describes responses that make you stand out without pushing people away, e.g. calling yourself dead inside, but crucially, not really meaning it.

The takeaway is to actually take the time to work with the specifics of someone’s profile. In this economy, you’ve got to be clever in order to catch someone’s eye. At the end of the day, there’s plenty of wiggle room between “hey” and “where have you been all my life, gorgeous.” Better to be a little weird than a little boring.