"Every December 31, I set a word that will become my intention for the new year. This year, the word was “rejection.” I vowed that this year, I would be brave enough to put myself out there in situations I previously had avoided out of fear that I would hear the word “no.” As someone who deletes and re-downloads Hinge approximately 27 times a year, I wanted 2024 to be the year that I got off of the apps and figured out how to ask someone out… and the whole flirting fearlessly thing has really paid off.
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I will not lie to you—it was nerve-racking the first couple of times I approached strangers IRL. Were they even single? What if they laughed at me? Am I even in their league? At the end of the day, I realized none of that matters because one day, being bold will help me meet my perfect person. I started at bars, where it felt the most socially acceptable to approach people, and then I would cross my fingers and go up to them. 90 percent of the time, I was welcomed.
If you’re in your approaching-people-IRL era, too, here is the inside scoop into some of my favorite pick-up lines that I’ve used, my friends have used, or I’m planning on using when the moment is right. Remember: People love confidence, and if they don’t, they aren’t your person. You have nothing to lose but everything to win.
For when you’re at the bar
We all hate it, but let’s be for real: The bar is a breeding ground for new connections and the perfect place to start if you’re not sure how to ask someone out. Be cheeky, have fun, and most importantly, be bold. Pretend you’re in an early-2000s sitcom and get to it!
- Hey! Is this seat taken?
- What’s your favorite drink? I’m just asking so I know what to order you on our first date.
- Do you have Instagram? My parents always told me to follow my dreams.
- Do you like tequila or vodka?
- What are you drinking? Follow up: Is that your go-to?
- Is this your favorite bar, or do you have another one you’d like to show me on our first date?
- Do you have any other plans for the rest of your week/end?
- Are you going to stare at me all night, or are you going to come talk to me?
- What’s your favorite song? Follow up by asking the DJ to play that song and dance the night away.
- Do you wanna grab a bite somewhere?
- Tell me two truths and a lie about yourself.
- Can I interest you in some mediocre conversation?
- So, what elaborate lie are we going to tell people about how we met?
For when you’re at the park
For those who want a bit more of a wholesome meet-cute, the park is the perfect place to approach someone. Don’t know how to ask someone out? I asked a guy on a run, and now we’re about to go on our third date. Live out your rom-com dreams this fall and approach that cute dog dad you see every morning.
- Hi! What’s your dog’s name?
- Ask if you can join in on whatever games they’re playing—any excuse to look cute on a pickleball court in a tennis dress!
- Hey, I don’t usually do this, but I think you’re so cute. Would you maybe want to exchange numbers?
- My friend over there thinks you’re cute… oh, it’s me, I’m the friend.
- Hey, do you maybe want to grab coffee after this?
- Do you always run here? I’ve never seen you before!
- Do you listen to music or podcasts while you run?
- What is your favorite part of the park?
- Hey, I don’t usually do this, but would you maybe want to go on a date?
- I think we should see each other again… you know, for our dogs’ sakes.
For when you’re at the gym
The gym might be one of the most controversial places to try to get a date, but for so many of us, the gym acts as our third place. We spend a significant amount of time there, so it would be a shame to never shoot your shot with your gym crush. The trick is to not be creepy—and while that’s easier said than done, in my experience, I have found being as friendly as possible will usually put an end to the stalker vibes.
- Hey, can you spot me?
- Hey, do you have any tips for [insert exercise], I see you’ve been killing it lately.
- I just tried this workout class, do you want to go with me next time?
- I don’t normally chase people, but I’d put my Crocs in sports mode for you
- Hey, I feel like I see you here all the time! Maybe we can work out together tomorrow?
- Do you want to grab a post-workout snack after this?
- Do you do cardio before or after your strength training?
- What pre-workout do you use?
- Hey, do you wanna go to the sauna together after our workout?
- I hope someone knows how to do CPR because you took my breath away.
For when you’re at the coffee shop
Much like the gym, most of us frequent the coffee shop almost every day. If it acts as one of your third spaces, why not see if it also can act as a meet-cute? Whether you’re on a first date or trying to secure one, the odds are in your favor—because everyone is happier after coffee.
- What’s your go-to order?
- How many cups of coffee do you average a day?
- Do you drink iced drinks even in the winter?
- Coffee or tea?
- Hey, can I pay for your coffee?
- So, are you loyal to this coffee shop, or do you like to try out new ones?
- Have you ever tried [insert specialty coffee from the coffee shop]?
- Do you have a sweet tooth?
- Hey, mind if I do my work with you?
- My coffee isn’t hot enough, could you hold it for a second?
For when you’re at the bookstore
The hopeless romantic in me is determined to meet my partner at the bookstore. I can see it now… I cannot reach a book, he grabs it for me, we lock eyes, end up having a marathon reading date at the coffee shop across the street, and the rest is history. Regardless of whether you’re a little delusional like me or not, there is something to be said about common interests when it comes to compatibility. Worst case, you leave with your new favorite book.
- What’s your favorite genre?
- Do you have a favorite author?
- What’s the best book you’ve ever read?
- Do you like paperbacks, or do you splurge for a hardcover?
- What’s your stance on physical books or digital books?
- I have a library card… do you mind if I check you out?
- If you could be a character in any book, who would you be?
- Do you read the book before the movie, or watch the movie and then read the book?
- Do you maybe want to go to a cafe or park and have a reading date?
- Hey, do you want to join my book club?
- I know I’m not supposed to judge a book by its cover, but one look at you, and I’m already hooked.
For when you’re at a singles event
One of my biggest fears is approaching someone and having them not be single. One way to eliminate that fear if you’re uncertain of how to ask someone out? Singles events. I’ve found them to be a great way to socialize with others and try out some cheesy pickup lines. Plus, if you’re not vibing with the person, you can easily move on to the next without having an awkward moment trying to get away. Check one out and try out one of these conversation starters while you’re there!
- What’s your ideal first date?
- What are your love languages?
- What’s your go-to karaoke song?
- What did you want to be when you grew up as a kid?
- Hey, you must be the guy that’s going to get me a drink!
- I dare you to send me your Spotify wrapped from last year.
- What are your green/red flags?
- What are the top three qualities you look for in a partner?
- If you had a theme song played every time you walked into a room, what would it be?
- What’s your favorite restaurant? Follow up: We should go there on our first date.
- Let’s flip a coin. Heads I’m yours, tails you’re mine.
- What’s your worst first date story?
For when you’re at the airport
It always seems to be at the airport when we see the hottest people that we instantly fall in love with. Like seriously, what is with the sexual tension you feel with anyone within your age range at the airport? Sure, while it probably will be a short-lived fling, who knows… maybe they live down the block from you, or you’ll find yourself buying a one-way ticket to move to Australia. Either way, who said you couldn’t catch flights and feelings?
- Where are you heading?
- Do you have any recs for [insert wherever you’re going]?
- What is your worst travel story?
- Do you travel often?
- Where is the best place to grab a bite in this terminal?
- When we land, do you want to continue this conversation over dinner?
- Where is your favorite place you’ve ever been?
- Are you the Bermuda Triangle? Because when I look at you, everything else disappears.
- Beach or Mountains?
- Do you like to explore on vacation or relax?
- Are you a carry-on or checked-bag kinda person?
For when you need to secure their number
While approaching someone IRL might be the hardest and most daunting part, make it worth it—ask for their number! Your witty self is a catch.
- When I text you tomorrow, what number should I use?
- There’s something wrong with my phone, it doesn’t have your number in it.
- 123456789, the only number I don’t know is yours.
- I bet my number sounds nicer than yours, wanna hear it?
- I have a phone number, you have a phone number, think of the possibilities.
- My friend doesn’t think I can get your phone number, can you help us settle this bet?
Bryanna Cuthill, Contributing Writer
Bryanna Cuthill is an NYC-based writer with a Bachelor of Music in Music Theatre from Baldwin Wallace University. Being a textbook hopeless romantic, and writing professional pretender on her taxes, Bryanna is no stranger to being delulu and achieving a teaspoon of success for every cup of rejection. She’s ambitious, outgoing, and loves giving advice on modern dating.