17 Online Dating Conversation Starters That Just Work

online dating conversation starters

Online dating conversation starters always seem like a hot topic for my private clients. This blog gets a fair amount of views. So, I decided to update this blog with a few of the best tactics we use for my private clients. (Shh, don’t tell anyone…)

The most effective conversation starter begins with good old-fashioned psychology tailored to the modern reality of online dating. (i.e. you “meet” someone virtually first rather than in person). From my experience, these are excellent conversation starters that get replies on a regular basis. Now, this doesn’t mean they always work, but I’ve seen them do wonders for my clients.

Full disclaimer: I am not a psychologist, a psychoanalyst, or any kind of psycho at all. I’m simply sharing legitimate techniques which prove to work for my private clients.

Online dating conversation starters may seem contrived or disingenuous, but it’s all in the way you deliver. Starting a conversation and keeping it going is a big part of the online dating process. To be successful, you need to get comfortable engaging with people you just met in a fun, non-threatening way, giving you an opportunity to get to know them.

Not all of your attempts to connect will be successful, it’s a number’s game after all. If you don’t get a response in a few days, forget it and move on. There are a million reasons why someone might not respond to you; not least of which is they are no longer online dating, but rather, the dating site has left their profile in place to make it look like they have more people on the site than they actually do (See How to Spot Fake Profiles).

Of course, there is also the possibility the person checked out your profile and is just not interested. Who cares! There are lots of other people to meet. You need to keep the right attitude when embarking on your online dating adventure.

My clients already know that online dating works, they just need a little help to make it work perfectly for them. Today, according to a study by toptal.com, 50 million Americans have used, or continue to use online dating sites. Based on an analysis by the Pew Institute, more than 30% of US adults have tried online dating, and the majority find it very positive. Of all the people using these sites and apps, 84% are looking for relationships. This is why online dating conversation starters are so important.  Aside from being introduced through mutual friends, online dating is now the second most popular way to meet someone.

But to avoid ending up being featured in articles about the absolute worst in pick-up lines, you might need a little help coming up with that perfect conversation starter to get things moving in the right direction.

I’m offering you my top 17 online dating conversation starters that are creative, funny, and allow you to get to know someone beyond the superficial level.

You can spend forever crafting the perfect online dating profile, but it won’t matter if you don’t know how to break the ice and get a winning conversation started!

Use these to help make you comfortable around each other before the first date rolls around! Everyone likes a nice compliment, but it’s important to be careful. Avoid mentioning the other person’s appearance as it can come off as creepy. You should only tell someone they’re beautiful/hot/gorgeous after you’ve met them in person and got the “ok” signals.

Once you break the ice, you can move on to ways to keep the conversation rolling. Remember to use my “3-2-1 Online Dating Technique” to get the most from your online dating experience.


Table of Contents:

  1. Play Detective, Examine Their Profile for Clues
  2. Ask Them What They Think
  3. Ask for a Small Favor
  4. Stir Pleasant Memories
  5. Shared Experiences
  6. Introducing a Negative
  7. Reference A Blast from The Past
  8. The Last Thing
  9. Share Vulnerabilities
  10. Ask About Pets
  11. Dream Big
  12. Play Desert Island
  13. Ask for Their Advice
  14. Consider Their Age
  15. Be Funny, If You Can
  16. Get to the Point
  17. Talk About the Future

Bonus Tip: Proofread Your Messages Before Sending Them



1. Play Detective, Examine Their Profile for Clues

Someone skilled at online dating will want to help others connect with them in a meaningful way, and maybe give them a little test to see if they are actually interested. A good online dater will leave clues, hints, and statements in their written profile you can use to start a conversation.

For instance, if you’re reading someone’s profile and they mention their favorite place to visit is Tucson, Arizona, then you have two options. If you’ve been to Tucson, share your story about it and ask them why they liked it so much. If you’ve never been, then ask them suggestions on where to go and what the secret to a great time.

People want to connect, or they wouldn’t be on an online dating site. The most successful online daters know they need to help others connect with them, and so they use the written profile and photo gallery to give you “hooks” to help you engage.

If you’re looking through their profile and see exotic travel photos or them running an Ironman competition (for example), then you know these are things they are passionate about. These photos give you an opportunity to reach out and ask them about their passion.

Everyone loves to talk about their passion, use this to your advantage. If you notice in their photos they’re doing something cool like bungy jumping, running a marathon, or skydiving, this can be used as one of your online dating conversation starters:

“Wow, I’ve never been bungee jumping before, how was it?”

“You’re so brave, good on you for skydiving!”

“Running a marathon is impressive, I’d love to train for one.”

You may read in their profile that they have a particular interest or achievement. Maybe they work in an interesting field or have a unique dream. Mentioning this in the form of a (playful) compliment can break the ice and show you pay attention.


2. Ask Them What They Think

A simple, non-threatening request for an opinion is a great way to kick things off. People love to show off how smart they are and can’t resist the opportunity to give their opinion.

This conversation starter revolves around making a statement and then asking for feedback from one (or many) of the people you’re interested in. For example, you could send a message and say “I just got a new profile photoshoot. I think it’s pretty good, what do you think of it?”

Another approach would be to ask something like,” Hi, can I ask you something …I just joined this and am wondering how you like it?”

dating profile

3. Ask for a Small Favor

This one is based on a technique Benjamin Franklin might use to start a conversation. It’s based on the concept of Cognitive Dissonance.

Basically, if you ask for a small favor and someone grants it, they are more inclined to like and engage with you. In the real world, this might be like asking someone, “do you know what time it is?” or another might be “Excuse me, do you know where is?

In the online dating world, you can start a conversation with something like “Can I ask you a favor, I just worked on my profile, can you tell me what you think?”

Another approach is to lead with a compliment: “I saw your profile/outfit/ profile photos, and I really like it. How did you do it?” This leverages the person’s profile to find something you can compliment.


4. Stir Pleasant Memories

Without going into the technical, psychological basis for this online dating conversation starter, people usually have fond memories of the physical place they grew up. I grew up in a small town in east Texas. While the circumstances were not always ideal, my memories of Kerrville are positive. When someone asks me about Kerrville, it makes me happy. You can use this to your advantage, sparingly.

If the persona mentions in their profile where they grew up or it’s discernable in some other way, then it’s fair to ask them about the place they grew up. For example, you might ask, “What was it like growing up in ?”  Or you could start a conversation with something like, “I just visited , what was it like growing up there?”

It’s important for you to stick to asking questions about the place and not about the relationships. Don’t ask about their family or family dynamics. Don’t ask about their schooling. These can all be negative triggers, and since all you want is to start a pleasant conversation, why start off on the wrong foot?


5. Shared Experiences

One thing you can be certain of is you are both using the same online dating site, meaning you probably live in relatively the same area. You can use this information to start a conversation by asking about shared experiences.

You could start a simple conversation by asking about their experiences in using the site. You might even ask them to tell you the craziest thing they’ve experienced using the site. Since you live in the same area, you can also ask them about their favorite local recreation activity, or any other generic, but geographically local, endeavors.

It’s important not to ask them about their favorite restaurant or specific places they like to go because you might come off as a stalker—nobody wants to start a conversation that way!

Start with something like “I just went to Dodger’s stadium, it was fantastic. Have you checked it out yet?”

Regardless, a shared experience can help you get a conversation off to a good start.


6. Introducing a “Negative”

I’m not really a fan of this one, but some people find this is a good way to start a conversation, allowing them to learn what the other person doesn’t like.

One of the best online dating conversation starters I’ve heard is, “So, what’s the worst date you’ve ever been on?”

It‘s a bit bold as an opener, but this reminds the person you’re messaging that we’re all in the same boat when it comes to online dating. It’s a way to make talking feel less like an interview or an audition and more like a chance to commiserate.

Plus, by asking this question, you can avoid making the same mistakes as their past dates. You’ll learn what food they hate if they’re turned off by people who come on too strong, or just where they don’t want to be taken.

In addition, this can sometimes give you an insight into the person’s personality. Their reaction to the question can help weed out people whose expectations are too high, or who just seem rude or cruel to others.


7. Reference A Blast from The Past

Nostalgia is everywhere. Pop culture always tends to trend positively. Show you’re in on the pop culture trends by throwing an unexpected online conversation starter someone’s way, asking what they think a celebrity, band, or reality show star is up to now.

Ask something like, “When do you think Justin Timberlake is gonna drop a new single?” or “If you had to hang out with a Spice Girl, which one would you pick and why?”

Another good conversation starter is, “Any idea whatever happened to ?” Even if people don’t know the answer, this can usually spark a conversation.

People hear the same three lines every day online–go beyond the mind-numbing “hey what’s up.”


8. The Last Thing

Starting a question with “What’s the last thing” allows you to fill in the blank with pretty much anything you want. Ask them about the last concert they saw, the last time they traveled, or the last movie they went to see. This is an easy question that will also give insight into the kinds of things they like.


9. Share Vulnerabilities

REALITY CHECK:  We all fall on our faces from time to time. Just brush it off and keep moving forward.

You’re looking for someone who is okay with laughing at their mistakes. Asking about embarrassing moments means you can gauge their comfort level with you, depending on how much they choose to reveal.

This goes beyond the shared experiences with the online dating site and the worst dates. This might be starting a conversation with something like, “One time in my High school lunchroom, I slipped and dropped a piece of pie right on the head of a girl I had a crush on. What’s the funniest thing that ever happened to you in high school?

dating profile

10. Ask About Pets

If you have/had pets, you can always use this as an “ice breaker” to start a conversation. Start with a short story about something funny or cute your pet does/did, then ask them if they have any good pet stories. This is works especially well if you see in their profile that they have pets because you can relate your story to their pet specifically.

Another “pet technique” if they have shots of their pets in their profile is to start a conversation with something like, “Wow! I see you have a Maltase. I have a secret power; I can guess the names of people’s pets. I see your pet’s name is ‘Snowball’ …did I get it right?”

This may seem like one of the more standard online dating conversation starters, but remember that whether they own a pet or not will have a big impact on how much time they can spend away from home. Asking if they have a furry friend will help you decide if you need to plan a date closer to home, so they can take the dog out if you decide to make the evening last a little longer.


11. Dream Big

The best online dating conversation starters are those that play into the sense of possibility and excitement that comes from a new relationship. Play into it by asking things like, “If money were no object and you could quit your job tomorrow, where would you go and what would you do?”

Everyone likes to have a fantasy and asking someone about theirs will help you get to know what they value most in life. Plus, it puts them in a dream-like state of mind.


12. Play Desert Island

Asking them to play this well-known party game is both fun and revealing. Send a message asking them to tell you which book, movie, and tv show they would take with them if they were going to be stranded on a desert island for the rest of their lives.

You could also ask which objects they would take with them. This is sure to reveal a lot about a person and their priorities.


13.  Ask for Their Advice

People love feeling like their opinion matters, so show the person you’re chatting with you care about theirs!

For example, if someone’s profile has a lot of travel pictures, or if their online profile photo references a clear hobby, ask something like, “Hey, I noticed you seem to travel a lot. Any suggestions for my 4-day weekend?”

This will allow them to talk about the things they’re passionate about, which is one of those great online dating conversation starters that helps you learn about a person, not a profile.


14. Consider Their Age

If you know the age of the person you’re messaging, it can be helpful when you’re planning your first message. Matches respond differently to openers depending on their age.

People between the ages of 18 and 23 like questions that are unique or surprising, such as: “Pain reliever personality test: Tylenol, Advil, or just complaining?”

People between the ages of 24 and 28 like lifestyle-related questions. Ask whether they enjoy sleep, exercise, or Sunday brunch. Another good option is to ask them to choose between an adventure like scuba diving, rock climbing, and skiing.

Those between the ages of 29 and 35 like to get a little personal. Ask to play a game like two truths and a lie, or “Have you ever?”

If you’re talking to someone who is 35+, pop culture is a good choice. Ask them to choose between two movies or pop stars and see what happens.


15. Be Funny, If You Can

Funny online dating conversation starters get lots of responses since most people enjoy having a laugh. Women are more likely to respond to a humorous message, and science has proven that women value humor when looking for a man.

Of course, guys are also more likely to respond if a woman makes them laugh. Send a GIF that will attract their attention and a humorous message to follow up. Start with a knock-knock joke or tell them a funny story.

For women, it can be a good idea to find some common ground based on their profile. Pick something from one of his photos and lightly make fun of him for it. Is that really his dog, or is he borrowing it in an attempt to attract women? Was it necessary for him to have his shirt off at that party?

This creates intimacy and also allows you to see if he can take a joke.


16. Get to the Point

This works especially well for guys. We all know that men are usually the more straightforward sex, which is why they’re 98% more likely to respond to an invitation. Consider “Drinks soon?” or “Free this week?” If you’re using an app like Tinder, you already know the other person finds you attractive since they had to match with you.


17. Talk About the Future

This can be a way to involve some humor as well. A simple question like “So, two kids, or three?” can get a laugh and show you’re serious about meeting someone.

Many people use dating apps and websites only for hookups. For people who are serious about finding a partner, it can be annoying to only get messages from people looking for a fling.

Demonstrating you’re looking for something a little more serious (even as part of a joke) can help you stand out from all the other people sending messages like “You’re hot,” and “Hey sexy.”


Bonus Tip: Proofread Your Messages Before Sending Them

Check your message before you send it. Make sure you’ve spelled the person’s name correctly if you’ve used it. Look for grammatical errors or spelling mistakes. You don’t need to be Shakespeare, but you also need to make a good first impression.



You’ll be ready to talk for hours with these online dating conversation starters. My clients want to get the very most out of their online dating experience, and they want to be successful online daters. Part of this is knowing how to start a conversation with anyone you’re interested in.

Conversation can reveal a person’s values, world views, hopes and dreams, expectations, and goals, and the big questions: are you compatible? Is it worth going on a date?

I have to remind my clients that online dating is a numbers game and not everyone is going to click with you. So, don’t over think it too much. Keep your conversation starters simple, be interesting, and if you don’t get a reply, move onto the next person.

These days, we’re all constantly glued to our smartphones, and meeting people through technology has become the norm. But it can be hard to stand out from all the competition if you don’t have any good online dating conversation starters.

Online dating conversation starters may seem contrived or disingenuous, but it’s all in the delivery. The question should come to you easily and naturally, so don’t ask your questions like you’re following a script. It will only be awkward and elicit a response you don’t want. I am giving you a list of some of our tried and true online dating conversation starters. Feel free to you use them in any order, or only ask one. The great thing about a conversation starter is that it starts the conversation. Once you ask one of your questions, the conversation will just go from there.

There’s nothing wrong with planning, especially when it comes to making a great first impression.

Now that you have some great ideas to get the conversation started, give them a try, and see how you do. You may even want to keep track of which conversation starters perform the best in different situations.


Claire BahnAbout the Author:

Claire Bahn has over 15 years of working as a personal branding expert helping clients build authority and influence through their online profiles and social media accounts.

Her background includes branding, public relations, Social Media, and marketing, as well as, entrepreneurship. She has a passion to help executives, entrepreneurs, and influencers strategize and create their best personal brand.

She is currently the CEO and Co-founder of Online Profile Pros and Stratus Branding. Ms. Bahn recognizes that first impressions are made online and the fastest way to achieving your goals is by taking command of your personal brand through your online profiles and social media. She started Online Profile Pros and Stratus Branding to help individuals create, maintain and protect their personal brands so that they achieve the authority, influence, and trust the need to succeed at online dating or their job search.

She’s been featured in numerous publications and news outlets including Forbes and Entrepreneur magazines.

Ms. Bahn is a former model and actress, appearing in national ad campaigns for major retailers. An avid fashion/lifestyle blogger she’s a recognized influencer. Ms. Bahn holds a BA from the University of Texas at Austin and currently lives in the Hollywood Hills in Los Angeles, CA with her 2 red miniature pinchers, Beau and Trixie.

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