14 Funny Online Dating Messages (First, Second, Third & Beyond)

Online Dating

14 Funny Online Dating Messages (First, Second, Third & Beyond)

Amber Brooks Amber Brooks • 6/28/17

On a dating site, a generic message is the kiss of death. You say “Hey, how are you?” and what I hear is “Please feel free to delete this message. I don’t care enough to try.” Impersonal greetings are just lazy, and I don’t have time to respond to hundreds of identical “sups” from people who may or may not be interested in me personally.

Maybe saying hi at a party works just fine, but online daters aren’t so easily wooed. According to OkCupid, “Saying ‘Hey’ in a first message is almost equivalent to saying nothing — this greeting has an 84% chance of being completely ignored.”

That first exchange sets the tone for the rest of the relationship, so you should go beyond one-word openers and say something to give your date a laugh. A solid joke can help you get your conversation off on the right foot — or at least up your odds of getting a response. You don’t have to be a comedian; just be original. We’ve collected 14 examples of funny online dating messages that tickle the funny bone and make a good impression.

1. Make a Joke That’s Specific to the Person

I once got a message reading, “So i looked at your thing, you seem pretty good.” Which didn’t exactly sweep me off my feet. I mean, I am pretty good, but you could send that message to pretty much anyone. And I’m betting he did. Getting personal and showing you’ve actually read someone’s profile is a much more compelling way to elicit a response.

Screenshot of Nguyet's Tinder conversation

Note: Making a personalized joke is funny. Poking fun at someone’s name is insulting.

Tickld has an example that only works on someone named Kassandra: “If you remove the D from your name, it’s an anagram for the word Arkansas,” a playful online dater wrote. Kassandra answered that she’d never heard that one before. He replied, “So I guess the question at this point is, do you want the D?” Which just goes to show that sometimes dick jokes can be done well if you’re clever enough.

An original, person-specific joke makes you stand out among vague come-ons. I know what you’re thinking — yes, this takes a bit more time, thought, and effort. But it pays to show you’re not simply copy and pasting a message to everyone online. Girls like that.

2. Use a Clever Opener to Turn the Tables on a Date

OnlineDatingAdvice came up with some hilarious and unique messages to catch someone’s attention — including one claiming the person is too attractive for the dating site. “I deeply regret that it is my unfortunate duty to bring it to your attention that you are above and beyond our maximum standards for looks,” the example message reads.

“Your account will be CLOSED unless you reply to this message with your name, phone number, your favorite flower, how many Cheetos you can fit in your mouth at once (just curious), and if you prefer Chinese or Italian cuisine.” — A funny first message from OnlineDatingAdvice

The messenger playfully asked for a phone number, implied plans for a date, and showed creativity with a unique format for a side-splitting message.

“This is very serious business,” the online dater warned in the message. “I would advise you not to take my message lightly or you might anger my boss Poseidon, lord of the seas.”

3. Start the Convo With a GIF

A GIF is an easy and amusing way to start a conversation on a dating app. It doesn’t take a razor sharp wit, but it still shows off your creativity. According to Buzzfeed, sending a GIF on Tinder increases your likelihood of getting a response by 30%. That’s a strong incentive to start adding GIFs to your dating repertoire.

Polar Bear GIF

GIFs are funny and flirtatious. Whether it’s Jimmy Fallon saying “Haaaay” or Joey Tribbiani saying “How you doin’?” a good GIF can get the ball rolling and make your date laugh.

4. Flatter & Amuse Using Humorous Compliments

An ideal first message references something in the dating profile and pays a specific compliment in a lighthearted (not creepy) way.

Screenshot of banter on a dating app

Many online daters pay compliments to personal appearance, so you can set yourself apart by complimenting a pet or a hobby.

The Virtual Dating Assistants (ViDA) gives a great example of the right way to give praise: “Wow… those eyes. That fur. How long have you two been together? Is he jealous of newcomers?”

In a funny first message, the online dater shows interest in Michaela’s pictures, pays a compliment to her dog, asks a solid question, and makes a flirtatious suggestion. All these elements combined create a memorable and appealing introduction.

The tone in this conversation is playful, which is what you want in those initial messages. You’re establishing a rapport. A little banter can endear someone to you and lead to a fruitful relationship based on good laughs.

5. Bait a Date With a Good Pun

I know a lot of people groan at the mere mention of a pun, but hear me out. Puns make good icebreakers because they’re witty and just a little bit silly. Sure, making a pun is on the cheesy side, but so is pizza. And pizza is delicious.

Screenshot of Leaona's conversation on a dating app

A clever quip can win someone over online.

Zoosk suggests something simple like: “What did the fish say when he swam into a wall? DAM!”

I personally enjoyed this gem of an opener courtesy of CollegeHumor: “I just saw the best upsexy.” The other person can’t help but reply, “What’s upsexy?” And you win the conversation. You’re welcome.

Is that joke immature? Yes. But it’s also hilarious.

If you ask me, a little wordplay is just good foreplay. Check out CollegeHumor’s Tinder puns for more clever quips to send first messages where the pun is definitely intended.

6. Harry Potter Pick-Up Lines Work Like a Charm

In my dating profile, I make it clear that I’m a huge fan of the Harry Potter series, so I’ve heard a lot of HP-related pick-up lines. And some of them are pretty fantastic. Here are a few good examples:

  • “Were you hit by Avada Kedavra? Because you’re drop-dead gorgeous!”
  • “Your smile is like Expelliarmus. Simple but disarming.”
  • “Accio response!”
  • “I know we’re not in Professor Flitwick’s class, but you still are charming.”

You don’t need a love potion to make a wannabe witch or wizard fall for you. All you need are some magic words from the wizarding world. You can find more funny one-liners for Potterheads here.

7. Study Up & Don’t Be Too Crude

Sometimes there’s a fine line between being original and being crass. You don’t want to take a joke too far. Remember, you’re talking to a complete stranger. Here’s an example of a funny online message that goes too far.

After matching on a dating app, Travis wrote the following first message: “Are you the SAT because I’d do you for three hours and 45 minutes with a 10-minute break halfway through for snacks, and then I would stare at you and think ‘Wow, I hope I don’t ruin this.'”

His desired fling answered, “You ruined it before you sharpened your pencil.” Ouch. As a general rule, sexual language and references in a first message are no-nos. You could end up alienating your date before you can send a second message.

8. Think Up Inventive Ways to Get Her Digits

Don’t overthink this. Your message doesn’t have to be the most wonderfully worded introduction ever. One anonymous conversation on Tickld shows that you don’t have to get too fancy to get a girl’s attention.

“So I’m writing a book right now,” the online dater wrote. When asked what the book was about, he answered, “Well it’s a phone book. And it’s missing your number.” Classic maneuver. The girl actually did respond with her phone number. Sure, she gave him her dad’s number as well, but at least it’s something.

9. Break the Ice By…Breaking the Law?

Dream3vil, an OkCupid user in Medford, New Jersey, took an original approach to his first message. He claimed he was pulled over by a cop for texting and driving because he was writing a message on the OkCupid app.

Screenshot of Dream3vil's message

Dream3vil turned a misdemeanor into a come-on in his message.

“I showed him your picture and explained what OkCupid was,” the online dater wrote. “He let me off with a warning and said I better get your number.”

Clearly, this guy is a smooth talker. He seems fairly proud of his run-in with the cop, and it’s bold of him to tell such an incriminating story right off the bat. In a way, it’s romantic. And hey, some girls are into bad boys who live on the edge, risking life and limb for their lady loves.

Dream3vil certainly makes an impression in his first message, and he even throws in a directive from a police officer to make it harder to refuse.

I don’t know if he won the girl over or not, but he made me laugh with his arresting anecdote.

10. Ask “Would You Rather” Questions

Conversation starters aren’t complicated. It just takes a little trial and error to acquire some stand-by icebreakers. Match suggests asking a “Would you rather” question to get a date’s attention. The dating site offers examples like, “Would you rather always find a parking space or always find your missing keys?” or “Would you rather be invisible or be immortal?”

You can get as imaginative as you want with it. You could ask, “Would you rather have a puppy-sized elephant or an elephant-size puppy for a pet?” or “Would you rather live in space or under the sea?”

These conversation starters are unique, interesting, and slightly silly so they’re ideal for anyone chatting online.

11. Settle Your Pizza Differences Right Away

Your first message should be indicative of your personality. SEO executive Oliver Brett revealed his go-to opener is the person’s name followed by an ellipsis. Women with his same sense of humor usually answer back, “Oliver…” and then he asks an important question: “Pineapple on pizza, yay or nay?”

“Yup, I only talk to strangers on the internet about pizza. And it works.” — Oliver Brett, SEO expert

Oliver loves putting pineapple on his pizza and joking around. His approach to online dating is playful and helps him quickly find someone who gets him.

12. Play on Stereotypes About Your Job or Major

People say, “You are what you do,” because that’s what your first impression will inevitably be. Oh, you’re an artist? So you’re a spacey, poor idealist. Such stereotypes can stop someone from getting to know you on a dating site where superficial judgments are common — but you can also use them to your advantage.

Tommy, a 26-year-old police officer, shows his funny side by writing, “Ever shouted, ‘Fuck the police’? Well, here’s your chance.” As a single cop, he must get a lot of people referencing his job and pre-judging him because of it. With one line, he shows that he doesn’t take himself too seriously. He also makes his intentions known, appealing to online daters with a rebellious side and a raunchy sense of humor.

13. Make an Ironic Invitation to Applebee’s

Sarcasm isn’t easy to achieve online, but if you strike the right tone, you can give your crush a chuckle. In a dating message shared on Tumblr, Jeffrey wrote, “Hey, I have a gift certificate for Applebee’s right now.” Not a classy beginning but mildly intriguing. “You get two apps and two entrees for 19.95,” he continued. “What time can my mom pick you up?”

Photo of an Applebee's restaurant

Jeffrey made a tongue-in-cheek invitation to Applebee’s to introduce himself to a date.

He’s definitely kidding. At least, we hope he’s kidding. The whole message gets more and more ridiculous as it goes on, but the awkwardness seems intentional. What I also love about this message is he keeps it clean. It’s a wholesome sentiment that leaves you with many questions. I imagine a lot of the responses Jeffrey gets are, “lol, are you serious?”

14. Come Highly Recommended — By a Pillow

Last of all, we have I Hedonist making a self-deprecating joke on OkCupid. “My pillow tells me I’m a good kisser…” he wrote. He’s keeping it light, showing some vulnerability, and flirting just a little bit.

It’s definitely original, but could be read as desperate, too. I’d add a winky face to soften the imagery and make it clear it’s a joke.

A Funny First Message Gets Your Foot in the Door

When sending a first message on a dating site, you’re better off saying “knock knock” rather than “hello.” A funny message stands out to online daters and increases your chances of getting a response. Oftentimes you can melt the hearts of jaded online daters with a clever quip or a quirky compliment.

Instead of being yet another generic profile, prove you’re someone worth getting to know by putting some puns, anecdotes, or jokes into your messages. If you can keep your date entertained and interested in that initial conversation, you’ll be in good shape moving forward.

Writing a funny and successful first message is an art, and we hope you can use our 14 examples of funny online dating messages for inspiration the next time you hit “send.” Good luck!