How to Flirt When Messaging on Dating Site or App

How to Flirt When Messaging on Dating Site or App with Plenty of Fish’s New Spark Feature

This is a Sponsored Post by Plenty of Fish.

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I first started looking into dating sites after 4 years of being out of a relationship. I had been burned in a really traumatic relationship and was single for 4 years. During those 4 years, I didn’t date at all for one entire year. I needed to heal myself from the experience and find out what I was really looking for in a relationship.


When I was ready to date again, I was older and wiser and not about to return to meeting potential dates at nightclubs anymore. I’m naturally an introvert so I wasn’t meeting guys during my daily routine: at the gym, coffee shop, or grocery store or whatever. Ultimately dating sites were the perfect solution.

Plenty of Fish is one of the top dating sites and apps in the world with over 150 million users!

The new Spark feature in the POF app really helps introverts like me! It makes it super easy for you to strike up a conversation with anyone that catches your fancy. On dating sites, getting conversations started with strangers online can be super awkward. With Spark you can just drag your finger over a conversation icon that pops up on your potential suitor’s profile to comment on their profile. It’s similar to how we already use social media and its the ultimate icebreaker.

Plenty of Fish has been testing the app in beta mode and found that your potential dates are 22% more likely to respond to the Spark, conversations starter feature. Studies show that users connect on Plenty of Fish more than on any other dating app!

Here are some online conversation tips:

How to Keep a Conversation Going On Dating Sites or Apps


  1. Ask Questions

Most people love to talk about themselves so give your guy a chance to share his world! Ask light, fun questions (use the POF Spark feature). The more he talks, the more conversation starters you’ll have and find the opportunity to compliment him whenever possible. This is also just a great way to find out if he is your ideal match.

2. Really Listen to His Answers

If he is a world traveler, ask him for the about his favorite bucket list destination. If he loves to BBQ ask him for a recipe recommendation.

3. Flirt

How might you ask? I’ll actually go into detail in the section below but in a nutshell, just add a little spice and playfulness to your banter. Keep it light though! Don’t go too sexual at this point. Emoticons are helpful for flirting

4. Be Positive

Don’t complain about dating, or work, or whatever. It’s too early in the dating process to be oversharing negativity!

5. Treat Him Like a Someone You Already Know

This will not only help make any jitters go away, it’ll make the conversation flow smoother. If you feel at ease, it’ll put him at ease too.

6. Be Yourself

And this means be honest! You want someone who wants you for you and the only way to find this is to be genuine and open

7. Reference His Profile

POF’s Spark feature is perfect for this! It gives you more to talk about if you comment on his photos and what he has written in his description and everyone feels good if someone has taken the time out to notice the little details. It’ll make you stand out from the crowd.

8. Don’t Be Defensive

Not everyone is comfortable chatting online and he might accidentally say something that you take the wrong way. Give him the benefit of the doubt and be easygoing! It’s not a good look if you come off as super sensitive before you even meet.

9. Set a Date

The goal here isn’t to find the ultimate online chat buddy, it’s to date in real life! After you have chatted a bit and gained some rapport, move the conversation towards how it would be great to actually meet him in real life!

I used to be the world’s most awkward person so believe me when I say that I used to have no idea how to flirt. I’ve learned to flirt some as time passed. Really flirting is just about having fun, being silly and playful. Touching him gently on the arm or chest works great (but this doesn’t work online obviously)

Here are some tips on flirting online:

How to Flirt When Messaging on Dating Site or App


  1. Start the Conversation Fun

Don’t just leave it at, “Hi How are you”. Maybe open the conversation with “There’s no way I can’t ask you about that selfie with the Tiger”. Give me the details!

2. Be Playful

Tease him, tell a little joke. Flirting is all about keeping things lighthearted. Just saw a funny meme online? Share it with him and ask him what he thinks.

3. Read Him and Adjust

Is he someone who likes long, detailed in-depth conversations, or does he keep it pretty light?

4. Ask Him Random Questions

If you run out of things to talk about, just ask silly but interesting questions. “What’s your favorite pizza or ice cream topping?”, “What are your favorite movies and tv shows”, which can then lead into: “Which character from Game of Thrones, Harry Potter, The West Wing are you most like”?

5. Use Playful Emoticons

Emoticons help so much with flirting! If you are teasing him, it’s great to end the comment with the winky face so he knows that you are not being serious. Don’t overuse them though! This can come off as childish and lame, use sparingly and at the ideal moments.

6. Be Confident

If he compliments you, just say “thank you”, don’t reply with a deprecating comment, that’s not cute or sexy.

7. End the Conversation

You don’t want the conversation to drag on until it becomes stale. After you’ve engaged and gotten a bit of good rapport, leave him wanting more! He’ll only have good memories of the conversation and you won’t be completely worn out with the conversation.

How did people even date before dating sites and apps? I’m so glad that the stigma of dating online these days is pretty much non-existent. It just makes so much more sense to start connections online since we live on our social media accounts anyways.

Ultimately using dating sites helped me so much, because I got myself out of my shell. There is this stigma in Los Angeles about how all the good guys are taken and that the guys in Los Angeles are too spoiled (beautiful women everywhere). Dating sites helped me to learn that there were good guys in Los Angeles, lots of them! I wouldn’t have met these good guys if I was still hanging out at the local bars or nightclubs.

My boyfriend and I had actually met in the before in real life. I had always thought that he was hot but he never asked me out! I reached to him once or twice over the years but he was always in a relationship. When I saw him on a dating site, I knew that he was single so I reached out and said hello! He was very responsive and quickly asked me out on a date. The chemistry on our first date was palatable and the rest is history.

I also want to mention that my cousin met her husband on a dating site, they are now married and expecting their first baby girl.

So get on POF and get your love life started already!

Download the Plenty of Fish app and find the one!

iOS app | Android app

This is a sponsored post written by me on behalf of Plenty of Fish.


  • Ppeople actually meet other people in real life …. that’s how we did it in the old dayz

    • not with millenials nowadays, its a whole new world!

  • Wow I like you post.
    Thank you for share with us.
    hope it will help us


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