Online Dating Conversations: The Best and Worst Messages To Send

6 min readJun 4, 2019


By Jessica Huhn for DateAha!

Photo by Nicole Honeywill on Unsplash

After carefully filling out your online dating profile, you’ve matched with someone who could potentially be your soulmate. Awesome! Now, it’s time to get to know them with the right online dating messages. An online conversation is just like any in-person conversation — you want to capture the person’s attention and keep them engaged, but you also need to use common sense and decency. If you wouldn’t say something to a person you’re talking with face-to-face, then you shouldn’t say it in an online dating message.

DateAha! has compiled a list of message types that will work great in any online conversation — and a list of message types that you should avoid at all costs.


Photo by Jamie Street on Unsplash

Having a successful online dating conversation is all about asking the right questions and following the flow of conversation. Try these types of question-centric messages:

A friendly greeting that includes a question for your match. This starts the conversation and doesn’t leave your match wondering how to follow up. Start with a question in the next category on this list…

Questions about your match’s interests, based on their profile. This shows that you’re interested in them and already took the time to get to know them. For example, if your match posted a picture of themselves playing baseball, ask about their favorite memories of playing the sport. Or, if they mentioned that they love Broadway musicals, ask who their favorite Broadway actor is and why, or what their favorite musical is and why.

Lighthearted, low-pressure questions that help you and your match get to know each other. Keep it fun! Ask questions about:

  • Their passions
  • Their favorite destinations
  • Recent adventures they’ve enjoyed
  • Their favorite foods, restaurants, and cuisines
  • What their ideal day would be like
  • Their media interests (favorite movies, TV shows, books, etc.)
  • Their hobbies
  • Items on their bucket list
  • Their favorite memories

Messages using the “What’s yours?” or “How about you?” technique.

  • Just answered your match’s question, like “what is your favorite place you’ve ever visited,” and aren’t sure what to say from there? Use “what about you?” or ask the same question back.
  • You could also share information about yourself (like your favorite movie), and then ask your match to do the same with “What’s yours?” Ex. “My favorite movie is Iron Man. What’s yours?”

Creative icebreakers that help you get to know your match’s personality. Try these:

  • If you could have any superpower, what power would you choose?
  • If you had to be an animal for a day, which animal would you be?
  • What’s the best piece of advice you’ve ever received?
  • If you won the big lottery jackpot, what would you do with the money?

You can find more examples of this type of question in my Medium article, “Questions To Ask (And Not To Ask) On A First Date.” In fact, any of the questions on the article’s “Yes List” are great for online conversations!


Photo by Efren Barahona on Unsplash

“Hey” by itself, “hi” by itself, “How was your day?” or anything similar, as a conversation starter. These messages are sooo boring. They won’t get anyone’s attention, and they show laziness. Come on, you’re way more creative than that!

“I love you” or “I think you’re my soulmate.” You haven’t even met the person yet — it’s way too early for weighty pledges like these!

“What are you looking for in a relationship?” Too many people ask this. Boring! Plus, this might open up an awkward situation — what if you don’t fit the description of what your match thinks they’re looking for?

Rants or negativity, especially about online dating.

Long-winded messages. Don’t send messages that are more than a few sentences long, and don’t go on and on about yourself. Shorter messages give both of you space to talk and listen — the ideal balance in any conversation.

Stories about heavy topics. Don’t tell stories of past relationships that didn’t work, financial struggles, family problems, illnesses, or other tough topics. Save that for after you’ve met in person at least once.

Personal questions. Just like you shouldn’t unload baggage on your match, don’t ask questions that would force your match to unload that same baggage. For example, don’t ask how their last relationship ended, how financially stable they are, or if they have any health issues. Save those questions until after the first or second in-person date.

Religious or political questions. These should be avoided until after you meet in person.

Questions about long-term plans for the future. This can throw your match under the bus and kill the lighthearted feel that online dating conversations are supposed to have. So, this is another question type that should wait until after you’ve met face to face.


Photo by Raúl Nájera on Unsplash

Copied and pasted messages that you’re sending (or planning to send) to multiple people. Your match can tell that you’re reusing these messages and not crafting messages especially for them. This also makes you look like a fake profile!

The unsolicited d — pic, or any unsolicited nude photos. You wouldn’t suddenly show your privates to someone you literally just met an hour ago, without their consent, to convince them to cultivate a relationship with you. That’s sexual harassment! Sending an unsolicited nude pic is the online equivalent of this unacceptable act — it’s also sexual harassment because the recipient never consented. And men, trust me. No one wants to see pics of your d — -.

A demand for nudes. It’s absolutely unacceptable to demand that a woman strip down in real life, without consent, so why do so many men think they can demand naked or partially naked pics from a woman online?

Racist or sexist remarks. Obviously. These are never appropriate no matter where you are, but I have to include this because some bad actors don’t realize this.

Sexually inappropriate or sexually aggressive messages. Seriously. Don’t send any sexually suggestive messages, and especially don’t ask for sex right away. That’s a surefire way to end a relationship, not start one — it makes things very uncomfortable.

Even when you know which messages to send (and not to send), finding a relationship on the web can be difficult and unsafe. After all, the people behind many dating profiles don’t want a long-term relationship like you do, but want to catfish you, scam you, behave inappropriately, or score a quick hookup. Ugh. You’ll probably end up receiving some of the messages on the “avoid at all costs” list, no matter how civil you are.

But what can you do about it?

If you face inappropriate behavior, your first instinct is probably to block the bad actor and report their behavior to the dating site. You’ve got the right idea, but this isn’t always effective. Dating sites usually don’t hold these bad actors accountable. So, toxic users think they can continue to do their dirty work with no consequence.

But what if there was a way for daters to hold people they’ve interacted with accountable for their behavior? There is — enter DateAha!

With DateAha, you can comment right on top of any dating profile to let other daters know if someone behaved inappropriately, fraudulently, or aggressively, whether online or in person.

The fear of negative feedback will drive out bad actors and make finding a healthy relationship easier.

Or, if you’ve had a good experience with a match (and simply thought they weren’t compatible with you), give them well-deserved positive feedback and help them on their way to finding a relationship!

DateAha! is here to make finding a relationship online much easier and safer. Use DateAha! for free comments and messaging on any dating site.




Bringing transparency and accountability to online dating by enabling comments directly on top of any profile for other daters to see and reply to — Me2.0