17 Online Dating Conversation Starters That Work Every Time!

Break the ice in an effective way!

By Claire Bahn — Written on Jun 07, 2020

Dating nowadays often includes "meeting" someone virtually first, rather than in person. And the most effective and excellent online dating conversation starters are tailored to modern reality.

They 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 successfully get to know people you just met and avoid ending up in articles about the worst pick-up lines, you need to get comfortable engaging them in a fun, non-threatening way.

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 wining conversation started!

Here are 17 online dating conversation starters that work every time.

1. Examine their profile for clues.

Successful online daters know they need to help others connect with them, so they use the written profile and photo gallery to give you "hooks" to help you engage.

For example, if you’re looking through their profile and see exotic travel photos or them running an Ironman competition, then you know these are things they're passionate about.

For example:

"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."

Their profile may list 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.

Make a statement and then ask for feedback. For example, say, "I just got a new profile photo. I think it’s pretty good, what do you think of it?"

Or, you can say, "Hi, can I ask you something? I just joined this [insert name dating site] and am wondering how you like it?"

3. Ask for a small favor.

Based on the concept of Cognitive Dissonance, 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?"

In online dating, it's 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, or 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.

People usually have fond memories of the physical place they grew up.

If the person mentions where they grew up on their profile, then it’s fair to ask them about it.

For example, you might ask, "What was it like growing up in your hometown?" Or, if you've been there, you can say, "I just visited your hometown. What was it like growing up there?"

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

5. Share your experiences.

If you're both using the same online dating site, you probably live in the same area. Ask about their experiences of using the site or about 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. Introduce a "negative."

This allows them to learn what the other person doesn’t like.

For example, "So, what’s the worst date you’ve ever been on?" is a bit bold as an opener. But, this reminds the person you’re messaging that you're 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.

By asking this question, you can avoid making the same mistakes as their past dates. You’ll learn what food they hate or just where they don’t want to be taken.

In addition, this gives you an insight into their 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.

Ask them what they think a celebrity, band, or reality show star is up to now.

For example, "When do you think Justin Timberlake is gonna drop a new single?" or, "If you had to hang out with a Spice Girl, who would you pick and why?"

People hear the same three lines every day online. Go beyond the mind-numbing, "Hey, what’s up?"

8. Ask, "What's the last thing... ?"

This 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 also gives insight into the kinds of things they like.

9. Share vulnerabilities.

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.

For example: "One time in high school, 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?"

10. Ask about pets.

If you have or had a pet, start with a short story about something funny or cute your pet does or did. Then, if they also have a pet, ask them if they have any good pet stories.

Another "pet technique" is if they have shots of their pets in their profile, start a conversation with something like, "Wow! I see you have a Maltese. 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?"

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.

Play into the sense of possibility and excitement that comes from a new relationship 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.

12. Play desert island.

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, revealing a lot about them 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, ask, "Hey, I noticed you seem to travel a lot. Any suggestions for my four-day weekend?"

This allows them to talk about the things they’re passionate about, which helps you learn about a person, not a profile.

14. Consider their age.

Knowing the age of the person you’re messaging 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 unique or surprising questions: "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.

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?"