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How to start a conversation on a dating app (without being boring, creepy, or cheesy)

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After I tweeted a joke and a screen of someone messaging me via Hinge, I read through many complaints (mostly from men), about how there seem to be only two options for someone who reaches out on dating apps.

Although I can understand the sentiment, this outlook is not good. False binary: “Get ignored” or “get ridiculed” There are many options for the middle path. You can have a conversation with a friend without sounding too boring, cheesy or cocky.

Bloggers, including myself, stress the importance of personalizing messages sent to dating apps. There is no way to be a single-size-fits all pick-up line in this market. If you wish to have a productive conversation, you must respond to a specific question in the profile.

This is why this article is so useful. How can I help? Unfortunately, I cannot take your phone out of your hands and swipe for you.

The thing is, we can predict a lot about what you will encounter on someone’s dating profile. These examples will help you to reevaluate your ability judge what’s funny and what’s not.

These are some conversation starters for dating apps. They are organized by the type of photos you will find on each profile.

  • If they have a concert pic…

A concert pic is often a way to start a conversation. You might be asking the wrong question by jumping in with observation rather than a question. Instead of saying “This looks fun,” ask something more open-ended like “What concert was it?” or “What are your plans for the next concert?”. If you recognize the musician or venue, that’s even better.

  • If they list the number of countries visited…

Photos of travel are a staple in dating profiles. Your instinct might be to ask “Where was this photo taken?” but I encourage you to ask a more open-ended conversation-starter. Being a well-traveled person, I prefer to be asked where I would like to go next rather than where I have been. It’s not easy to translate the “crazy travel story prompt” into text. It often ends in a one-sided, “you had better be there” moment. Bucket lists, on the other hand, allow for plenty of space for flirty, playful back-and-forth.

  • If they post a picture with a fish or reference the trope…

Pic of the good old “I caught fish” pic. A mutual message on Twitter gave me the perfect way of standing out among all the other fish in this sea. You could reply to a profile prompt such as “If you’re holding dead fish in your photographs, I’m no interest,” and then say, “I’m holding dead fish but if you would prefer to hold something inside, we could cuddle.” This is the perfect amount to make you stand out.

  • You can compliment their looks by…

Not everyone is looking for a soulmate. You don’t have to swipe on someone just because they are hot. It’s okay to be original and tactful about it. It sounds like someone copied/pasted your “Wow, you are gorgeous” comment to one hundred profiles. Physical compliments can sound unpersonal and can be off-putting.

Hot people should be treated the same way as you would for their personality. Revolutionary, I know. You can message them to ask where they went on vacation if they have a photo of themselves looking gorgeous on a sunny beach. The beach is what you should be focusing on, not your body. Your chances of standing out are higher if your profile is more interesting than you think (even if it’s only superficial).

  • If you found their profile funny…

Let them know why. I have received a few “you look funny” DMs, and it’s not to brag. My wit isn’t good at this. Use the initial compliment to start a larger conversation. This could be “This reply reminds me of [favorite comedian]” (or “This is funny, I’d like to know what shows/movies make you laugh right now”) or any other approach. Even if you are grasping at straws this gives the person something to work from.

Oh, and what if you are a comedian? Have fun! You can build on the jokes they share. It’s always sunny back and forth is the best way to show your love connection.

  • If they are a niche meme…

It can be tricky to include a meme in someone’s dating profile. While it can be an efficient way to signal your sense of humor, it’s not always a productive conversation-starter. If you see a “tag yourself” element, go for it. I would avoid the temptation of the meme and reply to a different photograph. You could also use the “you made me laugh!” approach described above.

  • If they claim “sarcasm …”is my second language…

Swipe left.

The bottom line: Be the coolest possible version of you

You must be you. Blah blah blah. You can be your best self by mastering the art of “casual strange.” This refers to responses that are unique and don’t make people uncomfortable, such as: You can call yourself dead inside but, crucially, it doesn’t really mean that.

It is important to take the time to learn about the details of each person’s profile. You have to be creative to attract someone’s attention in this economy. There’s plenty of room between “hey” or “where have I been all my life, stunning.” It’s better to be a little strange than a little boring.

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