16 Ice-Breakers Every Single Should Know

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Ah, breaking the ice. Small talk. Introductions. Icebreakers.

The bane of online daters, am I right?

Whether it's starting an online message, sparking a conversation with a stranger, or the start of a first date, it can be awkward trying to get to know a stranger! Enter the bucket list of icebreakers.

So, what are some foolproof options every single keeps in their back pocket? Let’s explore!

Online and telephone icebreakers:

I have written before on good icebreakers for getting to know a stranger, as well as how to craft a good first message. Due to the nature of messaging and voice-only calls, the only things which can work as icebreakers are questions and comments (Check out the link in the video chat section next!). Texting, however, offers a few extra options!

  • Swap pictures of something interesting from your day. Whatever presents itself as funny, entertaining, or cheerful, just snap a photo and text it! The only caveat is to limit your sharing to one picture a day—after all, you shouldn’t text your match all day!

  • Text your favorite recipes to each other. Bonus points if you try to make them and report how they turned out! This is extra fun if you have wildly different tastes in cuisine. Or if one of you routinely relies on microwave meals, and the other is a chef for a living.

  • Send a few gifs and make your date guess what movie/show they are from. It’s way more fun than just asking what their favorite movie or show is. And who doesn’t love a fun guessing game?!

  • Take a going-to-church selfie on Sunday and ask for one of them going to Mass, too! It’s a fun way to see more of your match before you actually get to meet up for that first date—and if you do this before/after church, you’re sure to be dressed well and looking good.

Video chat icebreakers:

I have already written a whole list of fun icebreaker questions, which you can use on the phone or on video chat to get things rolling. But sometimes, you want to think outside the box instead of just asking questions back and forth. Enter this list of technology-friendly, unconventional icebreakers for that first call!

  • Grab an item connected to your hobbies: Introduce your pet! Or your favorite plant. Or even your best spatula. Whatever you like to do in your spare time, find an item you use and keep it on hand. It’s easy to pick it up and show your date! Plus, who wouldn’t love answering the video call and hearing “I’d like you to meet my go-to paintbrush!”

  • Play the music game: Hum your favorite song, and see if your date can guess what it is—this is more entertaining the less good your singing voice is! Or if you’re musical, play your favorite thing on an instrument. Or, you can make like my family and play “Song By Association” game. Music is a great way to connect, because on a phone or on video, it synchronizes immediately with the other person’s speaker.

  • Choose your background with intention: maybe you set up your video chat in front of your favorite artwork, or where you hang your guitar, or in your beloved garden. Besides your face, the background is the only thing your date can see—so use it well! It’s easy to start a conversation by pointing to something in your background, and talking about it.

  • Flip the camera to show what you’re both facing—even if it’s just a wall! This is along the same lines as choosing your background intentionally. Flipping the camera to show your current view gives your date more perspective of where you are. And bonus, it gives you a break from being viewable on the camera for a couple of minutes. Perfect for calming those nerves a little!

First date icebreakers:

Check out this post to plan a foolproof first date! This is a great place to start bringing in physical items as icebreakers. Since you’re sharing a real environment for the first time, you can add something to it to make your date start off on the right note!

  • A book: If you or your date is a reader, bring a book to show them. You can share your reviews of a mutual favorite, introduce them to a new author, or just page through to find your favorite quotes. Also, this gives you a sneaky way to ask to see them again: “You’re welcome to borrow it—I’ll get it back next time we go out!” You could also leave a bookmark with a flirty note hidden in the pages! (I used to be a librarian, can you tell?)

  • Card game: You can always whip out the classic first-grade favorite, Go Fish. Loser pays for coffee!  Even if the date is clearly not going to lead to a second, you can enjoy an easy game together. (And gentlemen, if you win the game, you can impress her by paying for coffee anyway.)

  • Smartphone: Your technology can come in handy here, specifically your photos. Share snapshots of whatever relates to your conversation—it could be hobbies, loved ones, places, etc. It’s a great way to connect, and your date can get a visual idea of your life!

  • Create a challenge: Play I Spy. See who can stack the most coins into a tower before it falls over. Or who can rewrap your silverware into a napkin faster. Or who can spot the most yellow cars on the road. Make a friendly competition out of anything your environment offers you! If you’re not sure where to start, the Internet has no shortage of fun challenges to try. (Just steer clear of anything involving eating, like the Cinnamon challenge or eating Tide pods. Be reasonable about this!)

Getting serious icebreakers:

If you get to this point, you should already have asked these important questions. You might not need any icebreakers, either, because you should know each other fairly well at this point! But nerves can strike at the most inconvenient times. It can feel really contrived when you are trying to ask for exclusivity! You can always fall back on these ideas.

  • The suave approach: “So they say if you make it to date three, you are a couple. What are your thoughts on that topic?”

  • The genuine question approach: “I’m at the point where I really want to keep dating you, and I don’t really want to date anyone else. How do you feel about being exclusive?”

  • The mysterious approach: “I’ve been wondering how you view exclusivity in dating—when would you say a couple is serious?”

  • The cheeky approach: “So are you going to start calling me your girlfriend yet?” With a wink tossed in, of course!

Remember, it's normal to feel awkward.

For any of the above, the biggest thing to break the ice is to acknowledge that you are breaking the ice. “This feels awkward.” “First dates are always kind of weird, right?” “This might be kind of uncomfortable to talk about, but it’s important, so I’m going to say it anyway.”

Dating naturally comes with levels of unsurety. It’s just part of the game! The way to succeed is not to avoid being awkward, but to power through it and keep trying. Keep putting in effort, keep practicing, and not even the most awkward conversations will be enough to discourage you!

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