20 Great Openings To Spark Conversations Online

Alexa Weeks | 07.11.16 | | Comments

During my experience with dating sites, often my inbox will be full of messages from matches that give me nothing to work with:

“Whats up?”

“How’s it going?”

“You’re so pretty”

“What’s your name?”

These are all pleasant messages, but none of them grab my attention enough to respond. When messaging someone for the first time, not only does your message need to stand out from all of the other generic ones, but you need to pave a path that can lead to a conversation!

The perfect conversation starter is an open-ended question that is unique.

Send a message that will catch their eye and engage them. Nothing too serious – this is the fun part!

Be playful

Try the following openers to spice up your online dating conversations. Save the serious stuff for later!

1. “Before we go out on a first date, I need to know what kind of toppings you like on your pizza…”

Who doesn’t like pizza? This is a sure winner – everyone loves pizza and your love interest will probably smile when looking at this.

2. “Hey, are you busy right now?”

Do you like puppies? You can follow up with the silliest question, but rest assured, this intro will hook their curiosity.

3. “Would you rather…?”

No one can resist answering these questions!


4. “Let’s go to Vegas and get married at a drive through. My car or yours?”

Obviously, this is a joke. Playful interactions are always a good place to start.

5. “If you were in a witness protection program, what would your new name be, and where would you live?”

A little imagination goes a long way.

Pay Attention

Check out their photos for props you can plug into conversation…


6. “I noticed that you play soccer. I do, too! How long have you been playing?”

Find something you both have in common, and run with it.

7. “I see a Pistons jersey in your photo. Have you been to any games?”

Even more points if that’s also your team, but don’t lie!

8. “Let’s say you and I hit it off really well…would you let me _________?”

Drive your truck/touch your beard/swim in your pool… You get the idea.

9. “Your dog is adorable. What’s its name?”

People love talking about their furry babies.

10. “Has anyone ever told you that you look like ______?”

Whichever celebrity you choose, make sure it’s a compliment!

Get to Know Him/Her

Dive deeper into information they’ve written about themselves.

11. “Where is your favorite place that you’ve traveled?”

Go ahead and share yours, too!

12. “2IntoBlue- Interesting screen name. What does it mean?”

Usernames can have a lot of significance behind them. Just ask.

13. “You’ve got a Bachelor’s degree, I see. Where did you go to University?”

The next question you can ask is about what they’ve studied, or what their favorite class was.

14. “I noticed you’re a basketball coach/chef/photographer. Can you teach me how to ______?”

Keep chatting and down the road, you can circle back to this opening for a possible first date.

15. “You like to cook, huh? What’s your specialty?”

This is another good opening for a 3rd or 4th date in the future.

Shots in the Dark

You never know…

16. “What is your idea of a perfect Sunday?”

Is this something you can get on board with?


17. “What Netflix series have you been completely obsessed with?”

If you’ve watched the same series, you have something in common. If not, you have a new show to watch together.

18. “You have $6 in 7/11, what are you buying?”

I promise you, no one has ever asked them this fun question!

19. “What are three adjectives your mom would use to describe you?”

You’d be surprised by how far a convo can go off of simple questions like this.

20. “On a scale of 1 to 10, how is this online dating thing going for you?”

You two can instantly bond about being in the same rocky boat.

After the initial conversation starters, keep the chit chat flowing with open-ended questions, and share a little bit about yourself. Give your potential love interest something to work with! Most importantly, relax, this should be fun! Once you both have gotten to know each other, and decide it’s time for a date, you should check out these top ten date ideas to really impress your date!

Alexa Weeks

Alexa is a writer, traveler, and self-proclaimed online dating expert from Seattle. From making mistakes, to falling in love, she’s experienced it all. Alexa is here to give you all the tips, insight, and advice you'll ever need in the world of dating and romance.

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