A Guide to Effective Icebreakers for Singles

If you’re anything like me, hearing the word “icebreakers” sends an automatic shiver down your  spine. It either reminds you of 1) the soul-crushingly boring games your corporate manager makes you play at your weekly team meetings, or 2) the icebreaker gum candy that just sent the famous Miss Peaches to the veterinary hospital this month. You can sit here and pretend you don’t know who Miss Peaches is, but we know you’d be lying. 

Either way, the associations connected to icebreakers aren’t great. But we are about to change that. Why? Because they’re an important part of the dating experience, and gaining a better understanding of how they work and what makes a good versus bad one can mean the difference between a date that leaves you smiling and a date so dull you want to pull an “Eternal Sunshine of the Spotless Mind” moment and get your memory zapped for good.

Merriam-Webster sums up the word “icebreaker” pretty nicely:

 “Something that is said or done to get through the difficulties in starting a conversation or discussion.” 

I love this definition because it’s simple, sure, but also because it reminds us that icebreakers don’t necessarily have to be “Two Truths And A Lie” or “Would You Rather?” In fact, they don’t have to be games at all. Your icebreaker can take many shapes and sizes, but when it’s all said and done icebreakers all fall under one of these two categories:

Verbal Icebreakers

A verbal icebreaker is pretty much exactly what it sounds like: Any icebreaker that uses language to bring ease into the conversation. This could be in the form of questions (whether asked in person or on a dating app), such as:

Notice how all of these questions touch on observations that the speaker made about their date’s online profile or something they’ve spoken about previously. This is because the best way to not only break the ice but leave a good impression is to show that you’ve been paying attention. No one wants to feel like the 15th person you’ve messaged today (even if they actually are). 

Verbal icebreakers can also be compliments (about all kinds of different things, not just looks, please). Some examples could be:

Depending on the delivery and topic, jokes can also be great verbal icebreakers. We’ll spare you the attempts at a couple of examples and say this: Keep it clean(ish) and make it specific to the person. Again, no one wants your sloppy seconds. 

Lastly, verbal icebreakers can (but don’t necessarily have to) take the form of games. If your brain hasn’t yet fried from Two Truths And A Lie or Would You Rather? feel free to give those two a try. There’s also Desert Island, 20 Questions, or some classic trivia. You could even plan your entire date on the latter and go to a Trivia Night at a bar near you. Who knows? Your giant, knowledge-filled brain (or endearing lack thereof) could be the thing that sweeps your date off their feet.

Non-Verbal Icebreakers 

Before the start of my junior year in college, I was preparing to move into a new house with my old high school classmate and her friend, Andrea, who I’d never met before. I’d always been slow to warm up to people, but within the first few minutes of meeting Andrea, she did something that immediately brought my guard down: She commented on the fact that we had shown up wearing practically the same outfit, laughed, then gave me a playful shove to the shoulder.

The physical touch was subtle, but that, along with the verbal icebreaker (the comment about our outfits) was enough to say “I’m comfortable with you, and therefore you’re safe to feel comfortable with me.” This is a perfect example of the power of a non-verbal icebreaker. 

Non-verbal icebreakers can be defined as any action that uses everything but language to bring ease to or establish rapport in a conversation. In the story above, Andrea chose to use a gentle touch to the shoulder to break the tension during our first meeting; however, this non-verbal icebreaker could also look like:

The list goes on, but you get the gist. Next time you go on a date, try out one or more of these and see how it goes. And, on the flip side, pay close attention to what your date does to help you feel more relaxed and at ease — you just may learn something! 

If you’ve made it this far in the article, you’ve probably gained a good understanding of the role that icebreakers play in the dating world. But for the sake of clarity, let’s break it down further and talk about exactly why they’re so integral in the search for love (or fun).

In essence, icebreakers have the power to bridge the gap between two individuals on a date who are, let’s be honest, probably nervous to be there. They could be perfectly compatible lovers sitting across one another at a corner cafe. But they never get the chance to realize it because no one manages to break the ice.

A joke, a gentle touch on the thigh, a genuine laugh during an awkward silence can be the hammer that shatters the wall of discomfort and awkwardness, clearing a path for each person’s authentic personality to shine. 

Finally, they can get to the juicy stuff. You know, chats about personal goals, preference between Harry Potter vs. Lord of the Rings, and favorite current artists. Icebreakers pave the way for all of the important stuff to reveal itself naturally. And maybe the relationship works out, maybe it doesn’t. But at least you’ll know you put it all on the table. Yup, icebreakers contain the power to do all that. 

I know what you’re thinking: “Tips for Starting a Good Conversation” sounds like the perfect title for a book an alien may read while visiting Earth for the first time, right along with “How to Use the Toilet” and “How to Walk Like You’re Not Keeping A Giant Secret.” But I’m telling you, when it comes to mastering the art of the icebreaker, it’s important to get down to the basics. With a foundational knowledge in creating engaging, dynamic conversations, you’ll be better able to sharpen your icebreaker game and take on the dating game with confidence. Here we go. 

Show Genuine Interest

Few things spark meaningful conversation better than a genuine curiosity in what the other person is saying. Open-ended questions, body language (such as nodding and reactive facial expressions), and follow-up questions let the person know that you’re tapped into the conversation and are committed to learning more about them. And if you’re not? Then you may be a jerk, and you probably shouldn’t be on the date in the first place.

Let Your Sense of Humor Shine

Lighten up a little and crack some jokes! This isn’t a job interview, after all. Humor can be a powerful tool in injecting some fun and laughter into the conversation that may have otherwise been awkward and slow. Once the laughs start to roll in, the real personalities start to reveal themselves. 

Our suggestion is to play it safe with the jokes at the beginning. Your date may just have the same twisted, dark, or sexual humor as you, but that’s something you’ll have to figure out along the way. So we recommend avoiding controversial or touchy topics that your date may find offensive. Even if you mean well, this can be hard to suss out upon first meeting.

Establish Respectful Boundaries

I’ll admit, this is a hard one for me because I’m a world-renowned yapper (and a nosy one at that). I want to get straight down to the good stuff — you know, childhood trauma, past relationships, deepest darkest fears, the whole shabang. But I know not everyone is an open book like me, so I’ve learned to reel it back in. Maintaining respectful boundaries helps the person I’m conversing with feel safe and comfortable in our shared space, and hopefully paves the way for deeper conversations to come in the future. Easy does it. 

Don’t Use a Pickup Line

It’s 2024, friends. We’re better than this! Pickup lines are insincere, boring, and unoriginal. Most people on the receiving end of them will know that you’ve used the same exact one on at least a dozen other people, and will be immediately turned off. As we’ve mentioned before, the person you’re talking to is likely to respond more positively to an initial text or greeting that’s specific to them, not something that sounds like you got from a Reddit thread. 

It’s one thing to understand the importance of icebreakers and another thing entirely to come up with ones that actually work. We already addressed some examples at the start of the article, but a few more can’t hurt.

1. Ask A Question Based on Their Profile

If we’ve said it once, we’ve said it a hundred times: Most online daters want to feel like the user they’ve matched with is paying attention. Have another scroll through their profile, take some mental notes on what you see, and use those notes to come up with some engaging follow-up questions. 

Let’s say you’ve matched with someone that appears to be a huge Swiftie. Your question could look like any of the following:

Questions like these show that you took genuine interest in the person’s dating profile, rather than treating them like just another Tinder match. 

2. Commit to the Bit

“I Think You Should Leave” is one of my favorite comedy shows. Naturally, I answered all my Hinge prompts based on a specific skit about ziplines (to help filter out those who aren’t fans, of course). The men I’ve gone on to match and have conversations with were those whose initial message was a quote from that very same skit, showing me that they’ve seen the show and have a top-tier sense of humor. In other words, they committed to the bit. And I respected that immensely.

Sure, not all profiles you’ll come across will be created based on a very specific episode of a sketch comedy show, but you get what I’m going for here. This is yet another example of how something as simple as paying attention to a person’s profile can go a long way in the world of online dating. 

3. Send a Song Link

Everyone likes music. And if you don’t? You’re probably a cyborg. Kick off the message thread with good vibes by sending through a song you’ve been listening to lately. Copy and paste the link and say something like: 

If they like the song, you’ve got something to bond over right off the bat. And even if they don’t, they’ll most likely enjoy the fact that you asked them for their take on it. Who doesn’t want to feel like their opinion matters?

It’s normal to get a little nervous (maybe even a little sweaty) when meeting a potential date in person. But having a few go-to icebreakers can help. Take a look at these real-life examples and let them open up a creative space for you to start brainstorming a couple of your own. 

1. Tell a Story

What makes first dates so awkward and scary is (surprise, surprise) the fact that you two don’t know each other yet. There’s no sense of comfort or familiarity. So, why not fake the familiarity? Tell them a funny, interesting, or wild thing that happened to you recently, or even something that you saw on the news. And do it like you’re talking to a friend you’ve known for 15 years. Some of the best dates I’ve ever been on started off with him or me saying something like:

Spill that tea, friend. It really gets the conversational juices flowing. 

2. Give a Polite Compliment

As I mentioned previously, you get extra points if these compliments have nothing to do with someone’s face or body. Compliments that touch on someone’s personality or interests show your date that you’re really here in the moment, taking it all in. Plus, meeting in person gives you the chance to not only demonstrate the sincerity of your compliment via your voice, but also play around with some gentle physical touch. 

You could say “This jacket looks really good on you” as you reach across and feel the material with your hands.

Or you could offer “This is such a cool ring, I’ve never seen anyone wear one like it before” while you gently brush your fingers over theirs. (The room is practically boiling over with sexual tension, can you feel it?!)

3. Play the “Are They On A First Date?” Game

Nothing takes the spotlight off of a ‘couple’ on a first date than focusing on other people who are, well, on a first date. If you and your potential boo are sitting in a public place (perhaps a bar, restaurant, or cafe), try making a game out of guessing who around you may be meeting each other for the first time. Or, if you get the sense that there aren’t any first-timers around, you could just start making up scenarios for every couple or table of two that you see. ‘Watch this scene from the romcom “Date Night” for inspo (start at timestamp 0:22). 

Your jokes can be based on their conversation, their body language or, if you want to get a little crazy with it, complete delusion. This is your chance to let your imagination — or sense of humor, hopefully, flow more naturally.

As much as we want you to get as creative and authentic with it as possible, remember there are limits or, at least, there should be. Some things are either better left unsaid, or should be bookmarked for a later date when things aren’t so fresh and fragile. Keep reading to find the three types of icebreakers that you should leave out of your dating repertoire. 

1. Offensive or Inappropriate Topics

I don’t know who needs to hear this, but insults are actually not the same thing as flirting — no matter what your first grade teacher may have told you. Although it’s true that some people appreciate a good “flirt to roast ratio,” there’s a difference between making a joke for the sake of being playful, and just being straight up hurtful in a backhanded way (also called “negging”). Some examples of negging are:

You also want to be careful about formulating your icebreaker around something that your date may find offensive or inappropriate. Unless it’s been established that the two of you are looking for a FWB-type situation, this means avoiding crude and sexual comments that could extinguish the romantic flame before it even gets the chance to light. 

2. Overly Personal Questions

As I mentioned before, this can be a tough one for people who are used to telling their business to everyone and their mom’s dentist’s cousin twice removed. But it’s necessary nonetheless. Some people take more time than others to feel comfortable sharing the “deeper” stuff, and appreciate when you respect that fact. This means avoiding questions like:

It could be that your date is the one to open up the floor for these kinds of questions. And if that’s the case, then you can choose to move forward by matching their energy. Otherwise, it’s better safe than sorry. 

3. Insincere Compliments

I get it — It can be hard to think of something nice to say to your match/date in the moment. But please, for the love of all that is good and holy, don’t offer a compliment that you don’t mean. Not only could this potentially hurt the person’s feelings (most people can smell a fake from a mile away), but it also ruins your credibility. If your match/date knows you’re capable of lying about something so small and needless, they’re naturally going to wonder what else you’re capable of lying about. It’s a lose-lose for both parties. 

Congratulations, you’ve made it to the end of our guide! You don’t win a shiny new partner, but you should be walking away with some useful insights to help you find one. You now know the vital role that icebreakers play in the world of online and in-person dating – now it’s time to start brainstorming ones that work best for you. 

With this new toolbox of knowledge by your side, we encourage you to put yourself out there on dates and apply the skills you’ve learned here, making sure to pay close attention to how your date responds to each icebreaker attempt you make. Some may be a swing and a miss — and that’s OK!

Take mental notes about what works and what doesn’t. The key is to deliver them from a place of authenticity, genuine interest, and respect. As long as you can check all three of these boxes, you’ll know you’ve done all you can do. The rest is up to the merciful — or merciless? Only time will tell — dating gods. Good luck!