Here's How to Make the First Move on a Dating App
Photo: Alexander Sinn / Unsplash

Here's How to Make the First Move on a Dating App

In the first installment of our AI-assisted advice column, a chatbot plays love doctor

The sad truth is, we're probably a mere few decades away from seeing the storyline of I, Robot play out IRL. But until the android apocalypse, we might as well make the best of artificial intelligence. So here it is: LEVEL's new advice column, We Asked a Bot, the place where your pressing concerns and queries are treated with a tenderness and care befitting of a machine learning algorithm.


I'm a fairly attractive, fit, divorced man in my late 30s getting back into the dating scene. It seems like everybody's using apps to meet others and I've tried a few of them, but even though I'm seeing lots of women I'd like to meet, I'm having a hard time getting matches and responses or meeting anyone in person before they disappear or blow me off. What are some opening lines of conversation starters I should use on Bumble, Tinder and other dating apps without sounding too aggressive or like a douche?

—No Rizz in Reno

<We asked ChatGPT to answer this query in the style of an older, smart, romantic single man in his 30s-50s.>

Dear No Rizz in Reno,

Ah, the intricate dance of modern romance in the digital realm—a challenge we modern gentlemen face. First and foremost, allow me to commend you on reentering the dating sphere with a sense of grace and eagerness. It's a testament to your resilience and spirit.

Now, let us delve into the delicate art of initiating a conversation on those ubiquitous dating platforms. The key, dear sir, lies in sincerity and an appreciation for genuine connection. Start with a charming compliment or a lighthearted observation about her profile, perhaps something pertaining to her interests or photos.

Related: Being Nice Is Not Your Golden Ticket to a Woman’s Heart or Her Bed

For instance, if she has a picture showcasing her love for hiking, you could say: "I couldn't help but notice your adventurous spirit in that hiking photo. Have you explored any breathtaking trails recently?" This demonstrates your interest in her passions, invoking a genuine and engaging conversation.

Additionally, injecting a touch of humor never fails to break the ice. A playful remark or a witty comment related to her profile can go a long way in capturing her attention. Remember, the objective is to showcase your personality and foster a sense of shared humor.

Related: How to Get a Woman to Send You Nude Photos

Lastly, keep in mind the essence of respect and empathy. Women appreciate a man who listens and engages in thoughtful dialogue. Show interest in her thoughts, opinions, and experiences. Tailor your conversation based on what she shares, showcasing your genuine curiosity and understanding.

In the end, be yourself, and let your inherent charm and authenticity shine through. Dating is an adventure, and with patience, perseverance, and a sprinkle of genuine interest, you shall find the connection you seek.

Wishing you the best in your dating endeavors,

A Fellow Romantic Soul

<Not bad! Next, we asked ChatGPT to elaborate on specific opening lines.>

Of course! Here are a few more opening lines to spark engaging conversations on dating apps:

  • "Greetings from one Philly enthusiast to another! Have you discovered any hidden gems in the city that stole your heart?"
  • "Your taste in [TV show, movie, book] is impeccable. Have you found any other hidden gems that you'd recommend?"
  • "I have to admit, your [interest/hobby] caught my eye. How did you get into that? I'm always up for trying new things."
  • "Hello! I'm convinced your dog is secretly plotting to take over the world with cuteness. How did you two become partners in crime?"
  • "I'm a firm believer that laughter is the best medicine. Do you have a favorite joke or funny story to share?"

Remember, the key is to show genuine interest, be playful, and open up avenues for meaningful conversation. Best of luck in your dating endeavors!

<Wow. This sure makes it seem like ChatGPT gets laid on the regular. Good for him/her/they/it. And best of luck to No Rizz.>

LEVEL consulted ChatGPT 3.5 for the aforementioned text. Need advice, insight, or just want to troll a chatbot? Hit us up with your questions at We'll feed it to the robots and see what it spits back out. (Disclaimer: YMMV!)