10 Unconventional Ways to Start a Chat Line Conversation

Starting a conversation on a chat line can be a daunting task—especially when you know nothing about the person on the other end. How do you go beyond the usual “Hey, how’s it going?” without sounding scripted or disingenuous? The truth is, your opening line can set the tone for the entire conversation, so it’s important to stand out!!

Conversation Starters

Here are 10 unconventional ways to break the ice on chat lines and get that phone date off to an unforgettable start:

1. “If you had a superpower for a day, what would it be and why?”
This question immediately shifts the conversation into a playful, imaginative space. It’s also a great way to learn more about what excites or interests your partner, without being too personal right off the bat.

2. “What’s one thing you’d love to learn if time and money weren’t a factor?”
People love talking about their passions. This opener reveals a lot about their ambitions and dreams while steering clear of typical small talk.

3. “I just tried [insert a new activity or food here] for the first time! What’s something new you’ve done lately?”
This approach not only shares a little bit about yourself but also encourages your partner to share something current and exciting in their life.

4. “Tell me something most people don’t know about you.”
It’s bold, but it’s effective. This line invites vulnerability and can lead to a deeper, more meaningful conversation right from the start.

5. “If you could trade lives with any fictional character for a week, who would it be?”
This can lead to a conversation filled with laughs, surprising revelations, and shared interests in movies, books, or TV shows.

6. “What’s your go-to karaoke song?”
A fun, lighthearted way to get the conversation going, this question can reveal a lot about your partner’s taste in music and their sense of humor.

7. “If we were to create a secret handshake over the phone, what would it sound like?”
A little silly? Sure. But it’s a great way to lighten the mood and create a sense of camaraderie and inside jokes.

8. “What’s the worst opening line you’ve ever heard?”
This one is both a conversation starter and a conversation continuer—it allows you to move past the typical lines and jump straight into a shared experience of how awkward phone dating can be.

9. “Describe your perfect Saturday morning.”
Everyone has a dream weekend plan. Whether it’s lounging in bed with coffee or going on a morning hike, this question can lead to a fun exchange about favorite pastimes.

10. “If you could only eat one cuisine for the rest of your life, what would it be?”
People love food—this question might spark a passionate discussion about favorite dishes, travel, and cooking.

Final Thoughts

The key to these unconventional openers is to use them as a jumping-off point. Pay attention to your partner’s responses, and follow up with curiosity and interest. The goal is to make your chat line conversations feel natural, engaging, and different from the rest. After all, the best way to make a connection is to be yourself—just with a touch of creativity.