20 Conversation Starters (Almost) Guaranteed To Get That First Date

The first date often feels like the hardest part of a relationship. After we get through the first date, the rest is up to our charm and chemistry. Right?

But believe it or not, there is something harder than the first date. We know, we know; it’s unthinkable that anything could be more shoulder-tension-causing than that fateful first meeting.

Usually, we’re stuck stressing about what to wear, what to say, and how loudly we should be laughing in order to guarantee a second date. We want to roll things back a step further, though. How do we get a first date in the first place?

In this day and age of instant connection on apps and websites, the asking-out-on-a-date can seem like a fairly large obstacle. But it’s time to take things into our own hands. We’re going to look at the power of pre-date conversation. This is the conversation that introduces two people and tries to get one of them to go out with the other one. Some might call them “pick up lines,” but we’re way too classy for that.

In this fast-paced world, being able to spark and hold a conversation is worth so much. These conversation starters will, naturally, lead us to the next step: a first date.

20 Respectfully Point Out Something Uncool


Uncool isn’t always everyone’s prerogative, but sometimes we can’t help ourselves. One of the best ways to start a conversation can actually be to stand up for what’s right. Zoosk reveals that commenting on someone’s snarky comment to a waiter, or even calling out someone who’s rude to another person on the bus can bond two people together.

This is because it shows off the instigator’s values and highlights their moral compass. Or, it could just be the fact that we like to bond with each other during negative events. Either way, it’s certainly a righteous way to make a connection!

19 Ask About Their Weirdest Job


Who knows what the answers will reveal! Starting a conversation can be as simple as asking a question. It’s just a matter of knowing which question to ask, which is why this one appears on our list. Any question that will get someone talking is a safe conversation starter.

People love to reminisce about their odd experiences almost as much as they love to talk about their jobs. Combining these two reasons might be what inspired Refinery29 to come up with this question. They suggest asking about a person’s weirdest job. Depending on how many professional experiences the person has had, we could be in for a long talk!

18 Ask A Question About Their Drink/Food


It seems obvious, but this is often a nice, neutral place to start when it comes to conversation. As those who like to overthink know, there’s much more that goes into conversation than just the words that we say. However, we can’t talk without using words. If that sounds like a no-brainer, that’s because it is.

Forget about the intention behind the interaction, and ask a neutral question. Elite Daily says that asking a question about their drink or their food is a good way to not only start a conversation but to also build into a conversation about likes and preferences.

17 Start A Conversation About Whatever Karaoke, Band, Or Open Mic Artist Is On


It doesn’t matter if we like or dislike the Pink Floyd cover band that’s currently warbling their way through a replay of The Wall. What matters is that we can talk about it. Refinery29 reveals on their list of conversation starters that discussing whatever event the two of you are sharing is a low-pressure conversation starter. Places like karaoke, concerts, and open mic nights all invite connection and conversation.

By starting a conversation about the shared experience, both of you will feel comfortable; it’s an even playing field, and it doesn’t feel intrusive. This easy conversation instigation means a higher chance of continuing the conversation throughout the night.

16 Don’t Feel Pressured To Make The First Move, But Maybe Look Approachable


One of the tips Psychology Today lists on their small talk guide is that there are two ways to go about starting a conversation: we can be approached, or we can approach someone. Both are equally valid when it comes to engaging in conversation.

Don’t feel pressured to make the first move, but “if you want to try to get approached, stand about 10 feet from [an] individual or group. Keep that head up and make a flicker or two of eye contact. Give it a minute to see if you’re approached or, if it’s a group, you get a wave or even word inviting you to join.” This keeps you open and available to a conversation.

15 If It’s At A Party, Inquire About A Mutual Friend


Okay, let’s say that we’re not out with our friends. We’re at a friend’s place, or maybe in a party room at work or in an apartment building. There’s no band and no questionable karaoke to bond over. What do we do?

Psychology Today says that shared events aren’t the only good, neutral conversation ground. Bringing up mutual friends is also a great way to inspire a connected conversation. Asking someone how long they’ve known the host, or even how they met them, can offer some shared conversation that will naturally lead into other, deeper discussion. And a deep conversation is the kind that leads to a first date!

14 Offer A Compliment, No Strings Attached


People love to feel good. They like to know that their style choices are appreciated or that they’re doing a good job today. Connectedness and appreciation is part of what makes us human. Offering a compliment, out of the blue, with no strings attached, is a great way to catch someone’s eye.

We’ve found that people love positivity, and a compliment shows that we’re not afraid to share that positivity. While it might require working up some nerve (after all, we so rarely find the confidence to chat with strangers as it is), the results are going to be very, very worthwhile.

13 Try Bonding Over The Bad

Believe it or not, bonding over the bad can be just as powerful as bonding over something that’s good. Psychology Today has a whole article on dealing with awkward dinner party talk, and one of the things that we loved was the fact that they suggest asking questions about events or experiences that were bad, negative, or awkward.

Why? According to Psychology Today, looking back on those sorts of events is often funny and leads to some hilarious discussion. Not to mention the fact that, if it’s a negative situation you two are connecting over, you’ll have something to look back on and laugh at later on.

12 Ask Questions, But Don’t Turn The Talk Into A Job Interview


Technically this isn’t a question to ask but rather a method of asking the questions. Starting a conversation is sometimes as easy as a smile. And at other times it’s as nerve-wracking as complimenting someone out of the blue.

Generally, though, the best way to approach a conversation is to temper the question-asking. Relate to what they’re saying and reveal some details about yourself as well. Psychology Today says that, while people love to talk about themselves, it’s better to err on the side of respectful discussion rather than asking too many questions and making it feel like a job interview.

11 Break The Ice With An Act Of Kindness


We’ve all heard about the pay-it-forward trend, right? This is where someone will do something nice for a stranger, like secretly buying them a cup of coffee and asking them to “pay it forward.” We’re taking over that trend for ourselves, however, as it’s also a great way to break the ice.

Paying for someone’s coffee, candy bar, or even jug of milk is a kind way to break the ice and to start a conversation off on the right foot. It’s also a little less in-your-face than buying someone a drink at a bar, which means people are likely going to be more receptive to any advance we make after.

10 Inquire As To What They’re Reading (Or Watching)


The classic fall back question, asking what someone is reading or watching, might sound like a boring way to start talking to someone. However, it’s actually one of the conversation starters that’s almost guaranteed to get a response. People love to share what they’re passionate about and especially like to share pieces of art that have affected them.

Psychology Today suggests this as a first date topic, but we think it’s suited to being a get-to-know-you lead-up query. This works especially well if you’re on public transit and sitting next to a cute someone watching a funny show on their phone or tablet. Though, maybe wait until they wrap up the episode before interrupting.

9 ...And Then Follow It Up With A “What Else Is Good” Question


The other benefit to asking about what someone is reading or watching? They usually have other things that they’ve watched or read that they can also recommend. This makes it the perfect conversation piece as you’ve got the rest of the conversation right there in each of your respective Netflix viewing histories.

Refinery29 says “what else is good” gives them the chance to ask about you, too: your preferences, your likes, and your dislikes. All in all, it’s just a great way to build a conversation. We’ve also personally been known to suggest watching TV shows together now and then, which might be too forward for some.

8 Ask For Advice


This is an uncommon tactic, but it can still work. Sometimes we have a bad day. We drop our coffee, we trip on a curb, or we run into an ex. Sometimes we’re just left chewing on a problem that we can’t quite solve. No matter what, that problem is going to be there. Why not talk about it?

If there’s someone who looks like they might be dealing with something as well, try asking them for advice. Talking to a third party about a problem can often shed new light on a situation. It can also make the askee feel valued, which might make them want to engage more.

7 Always, ALWAYS Ask About Their Dog


Seriously, just do it. Even if someone doesn’t like dogs (but, then again, who doesn’t have at least a little soft spot for those fluffy babies?) they’re still a great topic of conversation. Dogs are like children. There’s always something new happening in a dog owner’s world.

Refinery29 says that this is a must-ask, and we definitely agree. Not to mention that this can easily build into a discussion about other pets, childhood pets, and animals as a whole. It might seem specific, but there’s really a vast amount of conversation that can be grown from this one slobbery topic.

6  Talk About Ideas, Not Just Experiences


Ideas are powerful, and sharing ideas can be one of the most important things two people can do. Elite Daily describes how it’s important to ask someone what they think about things other than what’s happening in the immediate present. This means asking questions, and probably being up to date on what’s happening in the world.

Talking about ideas is one way we get to know people. We can learn about their ideas and values and can figure out our true compatibility with them. Asking someone about things like an idea that they’ve had for an invention or even an idea for a novel or song can teach us a lot about a person.

5 A Safe Bet Is To Ask About Their Work Or Studies


When all is lost, we can always fall back on the classic work-or-studies question. Asking someone what they’re studying or what they’re working on is an easy, effective way to launch a conversation. After all, who hasn’t used this as a way to start talking to someone before?

Asking what a person does for work is much more interesting than asking where they work, as well. Letting someone describe their job in their own words gives insight into who they are, and what qualities they value, as well. It might be a safe bet, but it’s a safe bet for a reason.

4 Ask A Follow-Up Question, Rather Than “One-Upping”


Here’s another conversation tip in general. Zoosk mentions how this is one of those habits that many of us do without being aware that we’re doing it. One-upping is what happens when someone tells a story, and then we tell another story that overshadows or overpowers them without acknowledging what they said.

Or, alternatively, actively saying something like “I’ve got something better.” It’s really easy to do, and can really easily shut down a conversation. But there’s a simple way to stop, and that’s to always ask a follow-up question. Ask a question about the story, and then share your own.

3 Keep It Light And Friendly, Rather Than Oversharing Everything

pinterest.com / @taylranne

On the topic of sharing, though, we need to remember that there’s a lifetime ahead when it comes to getting to know the person in front of us. Psychology Today mentions how it’s not exactly appealing to overshare everything right away. Keeping it light and friendly is all we need to do when first getting to know someone.

Figure out if the basic interests are compatible, and then dive into the deep stuff. Conversation is easily won with a simple question; it can quickly become overburdened by sharing too much too quickly. That’s not the tone that makes for a smooth “will you go out with me” transition!

2 Try Subtly Restating What They Just Said


One conversation tip that comes directly to us from Psychology Today is the idea of mirroring the language of the person we’re talking to. Subtly restating what was just said, “will show that you've been listening and will also allow your conversation partner to clarify if in fact you are way off in your judgment.”

While the tip might be more geared towards the continuation of a conversation, we believe that this even works for starting a conversation as well. It can engage you with a person without forcing you to come up with something original to say and will start you two on a similar ground.

1 Look Into Their Future (But Not With A Crystal Ball)

pinterest.com / @hbybeee

After successfully starting a conversation, it can feel a little awkward to abruptly ask if they want to go out. Refinery29 says that one of the best ways to transition into that first-date-question pop is to ask about their week ahead. This will give us an idea about how they spend their time, as well as how they might want to fit a date into their schedule.

If they mention that they work early, but have their afternoons free, it’s easy for you to suggest a coffee or late lunch date rather than drinks. Since you’re working with their schedule, it’s (almost) guaranteed to get a yes!

Sources: Psychology Today, Refinery29, Zoosk, Elite Daily

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