How to Ask Someone Out on a Date
How to Ask Someone Out on a Date
Bon chance, lover! <3
“Young lovemaking — that gossamer web! Even the points it clings to — the things whence its subtle interlacing are swung — are scarcely perceptible; momentary touches of fingertips, meetings of rays from blue and dark orbs, unfinished phrases, lightest changes of cheek and lip, faintest tremors. The web itself is made of spontaneous beliefs and indefinable joys, yearnings of one life to another, visions of completeness, indefinite trust.”
― George Eliot, Middlemarch
A single friend recently told me that the dating experience for men is like looking for a glass of water in a desert, and the dating experience for women is like looking for a clean glass of water in a swamp. It’s rough out there. This guide gives you confidence in your noble pursuit of love.
Author’s Disclosure: This guide is written from the perspective of a woman for men. She welcomes any contributions, suggestions, and disputes. Courtship is a cat that can be skinned in more than one way.
Asking a Stranger
Start Here
Start with a Friendly Introduction: Begin with a simple, "Hi, I'm [Your Name]. I couldn't help but notice [something about the person or the context you're in], and I thought I'd come over and say hello." This approach is non-intrusive and opens the door for a natural conversation.
Comment on a Shared Experience or Environment: If you're both in a particular setting, like a coffee shop, event, or bookstore, mention something relevant to the environment. For example, "This coffee shop has the best espresso. Have you tried it?" or "This author's work is fascinating. Are you a fan as well?" It creates a common ground and eases into a conversation.
Compliment Genuinely: Offer a sincere compliment that's not overly personal. Focus on something like their style, choice of book, or even their pet if they have one with them. "I love your style; it's very unique. Where do you find your inspiration?" Compliments should feel respectful and genuine.
Express Your Interest with Confidence and Courtesy: After a brief chat that helps you gauge their openness to conversation, express your interest. "I've really enjoyed talking to you. Would you be interested in continuing this conversation over coffee or a meal sometime?"
Be Respectful of Their Response: Regardless of their answer, show kindness and respect. If they say yes, you might say, "Great! Could I get your number so we can plan something?" If they're not interested, thank them for their time with a polite, "No worries at all. It was nice chatting with you anyway!"
Suggest a Public Place for the Date: This makes the invitation feel safe and low-pressure. "There's a great café nearby I think you'd enjoy. Would you like to meet there this weekend?"
Keep It Light and Positive: Throughout the conversation, maintain a positive and light-hearted tone. This shows that you're someone enjoyable to be around and that you respect their comfort and boundaries.
Exit Gracefully: Whether they accept or decline, exit the conversation gracefully. "Well, I should get going. Thanks for a lovely chat!" This leaves a positive impression, regardless of the outcome.
General Talking Points
Hi, I don’t mean to bother you, but you seem to have really cool energy.
I’m <name>, and I’d really like to buy you a cup of coffee or tea if you’d be open to it.
Hi there, I'm [Your Name]. I couldn't help but notice your [comment about something observed] and thought it would be nice to introduce myself.
This [event/place] really is something, isn't it? What brings you here today?
I love how you've put your outfit together, it really stands out.
I've really enjoyed chatting with you. Would you be interested in grabbing a coffee or a bite sometime?
It's totally fine if you're not up for it, but I had to ask because I'd love the chance to continue our conversation.
How about we meet at that cozy café on Main Street this Saturday? It's got a great vibe.
It's been a pleasure talking to you. I hope we can do it again sometime.
Well, I should get going. Have a great day and hopefully, I'll see you around soon.
Asking a Coworker
Seriously. Don’t do it.
HR complaints, awkwardness at work, just no, man, no.
There are 7 billion people on this planet. If you can find someone, you can find them outside of work.
Asking a Friend
Start Here
Note: Know that this WILL change the context and dynamic of your friendship. In other words, “there’s no going back, pal!”
“We’ve known each other for a while now, and I’ve always wanted the chance to know you more.”
Talking Points
Would you be open to having dinner with me this weekend?
No matter your answer, I will continue to be your loyal friend.
Listen, if we go out and we don’t vibe, no harm is done. Ok? No awkwardness or hurt feelings. We’re friends who can speak candidly about our feelings. I know that the heart wants what the heart wants, and the mind has very little to do with it sometimes. We don’t get to choose who we catch feelings for. That’s life, and I’m confident that we can both be understanding about that.
The best advice I’ve read on this particular issue
In response to the following question, “How can I ask her out in a way that minimizes the risk of making our friendship weird?”:
Contrary to popular belief, you can ask her out and still remain good friends if she rejects you. This is simply because what destroys the friendship isn't asking her out but rather making a fool of yourself when she rejects you. This worst-case scenario would unfold like so:
You wait for too long and catch way too many feelings. When you ask her out, you're totally lovesick. You arrange a beautifully romantic date in a secluded spot, with rose bushes and everything, perhaps you extend a trembling hand and offer a wad of love poems you wrote for her, and then you're overcome by your feelings and you become a bumbling fool, and you move in for the kiss...
In the movies, she kisses you back with violins and everything. In real life, maybe she does if she's interested. However, if she's not interested and "doesn't see you like that" then...
The "beautifully romantic date in a secluded spot" is a tricky situation to get out of.
Your investment puts high pressure on her. You created a situation where rejection is difficult, awkward and costly for her.
If you drove her there, then you will have to endure all the drive back in total awkward mode.
If you start crying (because you're too lovesick, remember) and she consoles you, she will consume the entire energy of the friendship in doing so, after which it will no longer exist.
We haven't hit rock bottom yet. This would be when, the next day, you get drunk, and then a wonderful idea hits you: you're going to ask her out again! Maybe it'll work this time. You start with a long apology, then follow her in the street as she walks away, and then you insist, and then... oh yes...
Your excessive feelings increase the likelihood that you will say the Stuff That Should Never Be Said, like "But I was so nice to you!!! Why do you reject me!!!" which is the totally nuclear option. There is so much wrong in this sentence, she will treat you like radioactive waste for the rest of your life.
Then, of course, the following week you learn that she's dating Chad from the football team, and you conclude that Chicks Dig Jerks and that women are evil for not wanting to date you, such a... a... such a NICE GUY! In other words, you cast upon yourself the cringy curse of the Nice Guy. You die alone, bitter, and a virgin, but at least the fedora looks good.
Another option is:
Rid yourself of the fear of rejection, as it is what will cause you to create the worst-case scenario above.
Do not fear awkwardness.
What you will say when you attempt to initiate the relationship (ie, ask her out) does not determine if she is attracted to you. Either she is already attracted to you because of looks, personality, and past behavior, or she is not. Asking her out doesn't need some magic formula or anything. Either there is attraction or there isn't. Asking her out badly can ruin it, but it can't create attraction.
Considering your current friendship, pick a low-pressure setting: you're both swiping through your favorite meat market app and showing each other matches and giggling.
At the appropriate point, just mention, "hey, why don't we date each other instead of doing this?"
She says yes: you score.
She stays silent and gives you the googly-eyed stare: wait five seconds and laugh it off. If you're lucky, she was actually interested and now asks you out.
She says no: you laugh it off and go back to browsing. No drama. Not fearing rejection means you don't get butthurt or whiny, and you do not exhibit Nice Guy symptoms…
Note: Edited for brevity
Big Freakin’ List of Pick-up Lines (use at your own risk)
If I said you had a good body would you hold it against me?
Are you a magician? Because you just cast a spell on me.
Did you hurt yourself when you fell from Heaven?
Are you a cat? Because you look purrrfect!
Are you tired? Because you’ve been running through my mind all day.
Hold out hand: “Hey I’m going for a walk. Will you hold this for me?”
I’m not a photographer, but I can picture me and you together.”
Are you a cake, “Because I want a piece of that.”
Are you a bank loan? Well, you’ve certainly got my interest.
If you were a triangle, you’d be acute one!
Your hand looks heavy, let me hold it for you.
I think you are suffering from a lack of Vitamin Me.
On a scale of to 10, you’re a and I’m the you lack.
Do you like Harry Potter? Because I adumbledore you.
Was your dad a boxer? Because damn, you’re a knockout!
Your lips look lonely. Would they like to meet mine?
I was wondering if you had an extra heart. Mine was just stolen.
Your phone has GPS, right? Because I’m totally going to get lost in those *insert color* eyes.
Would you grab my arm, so I can tell my friends I’ve been touched by an angel?
Can I have your picture so I can show Santa what I want for Christmas?
Your body is 65% water and I’m thirsty.
Excuse me, do you have a band-aid? Cause I scraped my knee falling for you.
Do I know you? Cause you look a lot like my next girlfriend/boyfriend.
Do you know what my shirt is made of? Boyfriend/girlfriend material?
They say Disneyland is the happiest place on earth. Well apparently, no one has ever been standing next to you.
You look cold. Want to use me as a blanket?
Are you an alien? Because you just abducted my heart.
Did your license get suspended for driving all these guys crazy?
For some reason, I was feeling a little off today. But when you came along, you definitely turned me on.
Can I borrow your phone? I need to call God and tell him I’ve found his missing angel.
Hey, you’re pretty and I’m cute. Together we’d be Pretty Cute.
Can I follow you home? Cause my parents always told me to follow my dreams.
What’s a smart, attractive man like myself doing without your phone number?
I seem to have lost my phone number. Can I have yours?
I’m lost. Can you give me directions to your heart?
I would say God bless you, but it looks like he already did.
Are you a parking ticket? Cause you’ve got fine written all over you.
Is your name Google? Because you got everything I am searching for.
Are you sure you’re not tired? You’ve been running through my mind all day.
Did I tell you I’m writing a book? It’s a phone book and it’s missing your number.
Is there an airport nearby or is it my heart taking off?
Life without you would be like a broken pencil… pointless.
Are you from Tennessee? Because you’re the only ten I see!
I must be in a museum because you truly are a work of art.
I’m not stalking you, I’m doing research!
If I could rearrange the alphabet, I’d put U and I together.
I’m no mathematician, but I’m pretty good with numbers. Tell you what, give me yours and watch what I can do with it.
Aside from being sexy, what do you do for a living?
Do you believe in love at first sight, or should I walk past again?
You’re so sweet you must be made out of chocolate.
I’m not good at holding conversations can I hold your hand instead
If I had a nickel for every time I saw someone as beautiful as you, I’d have five cents.
Do you like Star Wars? Cause Yoda only one for me.
Go ahead, feel my shirt. It’s made of boyfriend material!
If you were a Transformer you’d be Optimus Fine!
Do you believe in love at first sight, or should I walk past you again?
I’m learning about important dates in history. Wanna be one of them?
I seem to have lost my phone number. Can I have yours?
Are you a parking ticket? Cause you’ve got fine written all over you!
Did you invent the airplane? Because you seem just Wright for me!
I was wondering if you had an extra heart…because mine was just stolen.
Are you Siri? Because you autocomplete me!
I hope you know CPR, because you are taking my breath away!
If I had four quarters to give to the four prettiest women in the world, you would have a dollar!
Let me guess, your middle name is Gillette, right? Because you’re the best a man can get!
Your eyes are bluer than the Atlantic Ocean, and I don’t mind being lost at sea.
If you were a burger at McDonald’s, you’d be the McGorgeous.
Are you a camera? Because every time I look at you, I smile.
Is there an airport nearby, or was that just my heart taking off?
Are you a loan? ‘Cause you’ve got my interest!
I’m in the mood for pizza. A pizza you, that is!
Are you a 45-degree angle? Because you’re a-cutie!
You’re so sweet, you could put Hershey’s out of business!
I’m good at algebra; I can replace your X and you wouldn’t need to figure out Y.
I’m really glad I just bought life insurance, because when I saw you, my heart stopped.
If I had to rate you from to 10, I’d give you a 9, because I’m the you’re missing.
You must be jelly, cause jam don’t shake like that.
You must be a bank loan, cause you’ve got my interest.
I’ve got 1-ply, I’ve got 2-ply, but all I really want is your re-ply.
If nothing lasts forever, will you be my nothing?
If you were a phaser on Star Trek, you’d be set to stun!
Is your name Google? Because you have everything I’ve been searching for.
Have you been covered in bees recently? I just assumed, because you look sweeter than honey.
There must be something wrong with my eyes. I can’t take them off you.
Are you from Tennessee? Because you’re the only Ten I See.
You must be a campfire. Because you’re super hot and I want s’more.
My buddies bet me that I wouldn’t be able to start a conversation with the most beautiful person here. How should we spend their money?
Well, here I am. What are your other two wishes?
Remember me? Oh, that’s right, I’ve only met you in my dreams.
You must be made of cheese. Because you’re looking Gouda tonight!
I’m glad I remembered to bring my library card. ‘Cause I am totally checking you out!
If you were a vegetable, you would be a cute-cumber!
I’m no mathematician, but I’m pretty good with numbers. Tell you what, give me yours and watch what I can do with it.
Are you made of Copper and Tellurium? Cause you are CuTe.
Are you an object with mass? Cuz i feel an attractive force around you.
Girl are those space pants? Because your butt is out of this world!
I think you’re suffering from a lack of vitamin me.
Kiss me if I’m wrong, but dinosaurs still exist, right?
Excuse me, is your name Earl Grey? Because you look like a hot-tea!
Can I borrow a kiss? I swear I’ll give it back!
If you were a vegetable you’d be a cute cumber.
Is summer over? Because I’m about to “fall” for you!
There’s a massive clothes sale in my bedroom – everything is 100% offI lost my number…can I have yours?
Are you a baker? ‘Cause those buns look TASTY.
I’m not a hoarder but I really want to keep you forever.
Is your name google? Because you’re everything I’ve been searching for.
Are you an onion cos I want to remove your layers.
Even if there wasn’t gravity on earth, I’d still fall for you.
I’m glad I brought my library card because I’m checking you out.
You don’t need keys to drive me crazy.
Do you know what my shirt is made of? Girlfriend material?
Do you smoke pot? Because weed be cute together.
Are those mirrors in your pants? Because I can see myself in them!
I was wondering if you had an extra heart? Mine was just stolen.
Are those space pants? Because your butt looks out of this world.
Is your name Chapstick? Because you’re da-balm.
Do you have a map? Because I’m getting lost in your eyes.
Do you have a bandaid? Cause I hurt my knee falling for you!
Are you my phone charger? Because without you, I’d die.
Like a broken pencil, life without you is pointless.
We’re not socks. But I think we’d make a great pair.
This may be cheesy, but I think you’re grate.
Did it hurt? When you fell from heaven.
I would like to select all of your clothes and press delete.
Did you sit in sugar? Because you have a sweet ass.
We’re you born a mermaid because you were a mermaid for me.
Your hand looks heavy; can I hold it for you?
Is your name honey? Because I’d love to drizzle you on my bland day.
Of all the beautiful curves on your body, your smile is my favorite.
I’m finding it really hard to breathe. You just keep taking my breath away.
Have you got the time… I’ve got the time if you’ve got the place!
Are you glitter because you add sparkle to my life?
Are you sitting on the Fkey? Because your ass is refreshing!
Let’s commit the perfect crime- I’ll steal your heart, you steal mine.
Do you wanna grab a coffee because I like you a latte?
Hello! I guess you are looking for Mr. Right. Well, that’s me!
My mom said she found a beautiful and intelligent girl for me. Is that you?
How does it feel to be so gorgeous?
What does it feel like to be the most beautiful girl in the room?
If you were a transformer, you’d be Optimus Fine.
Do you know what’s on today’s menu? It’s Me ‘n’ U.
Are you a doctor? Because my heart beats faster when I see you.
Are you Australian? Because you meet all of my koalafications.
Are you Space Shuttle Challenger? Cause I want to explode inside of you.
Not even Fahrenheit, Celsius, or Kelvin can measure how hot you are!
Let me tie your shoes, because I don’t want you falling for anyone else.
I don’t have a library card, but do you mind if I check you out?
Are you an orphanage? Cause I wanna give you kids.
Do you have a sunburn, or are you always this hot?
I was feeling a little off today, but you definitely turned me on.
Are you a fruit, because Honeydew you know how fine you look right now?
Do you live in a corn field, cause I’m stalking you.
Sorry, but you owe me a drink. [Why?] Because when I looked at you, I dropped mine.
Excuse me, is your name Earl Grey? Because you look like a hot-tea!
I’m not a hoarder but I really want to keep you forever.
Do you have a Band-Aid? Because I just scraped my knee falling for you.
Are you a parking ticket? ‘Cause you’ve got fine written all over you.
Are you mexican? Because you’re my juan and only!
Do you drink Pepsi? Because you’re so-da-licious!
Do I know you? Cause you look exactly like my next girlfriend.
I’m no organ donor but I’d be happy to give you my heart.
I seem to have lost my phone number. Can I have yours?
Is your nickname Chapstick? Because you’re da balm!
I’m not staring at your b00bs. I’m staring at your heart.
Can I take your picture to prove to all my friends that angels do exist?
I’ll give up my morning cereal to spoon you instead.
Do you want to see a picture of a beautiful person? (hold up a mirror)
I’m not drunk; I’m just intoxicated by YOU.
I was blinded by your beauty… I’m going to need your name and number for insurance purposes.
Is there an airport nearby or is that just my heart taking off?
There must be a light switch on my forehead because every time I see you, you turn me on!
Hi, I’m writing a term paper on the finer things in life, and I was wondering if I could interview you?
Have you been to the doctor lately? Cause I think you’re lacking some Vitamin Me.
Can I follow you home? Cause my parents always told me to follow my dreams.
You look so familiar… didn’t we take a class together? I could’ve sworn we had chemistry.
Hi, I’m Mr. Right. Someone said you were looking for me?
Do you like Nintendo? Because Wii would look good together.
If you were a flower you’d be a damnnn-delion
If you were ground coffee, you’d be Espresso cause you’re so fine.
If I had a star for every time you brightened my day, I’d have a galaxy in my hand.
Damn, if being sexy was a crime, you’d be guilty as charged!
I was wondering if you had an extra heart? Mine seems to have been stolen
I thought happiness started with an H. Why does mine start with U?
Are you a campfire? Cause you are hot and I want s’more.
If you were a tropical fruit, you’d be a Fine-apple!
Are you a banana? Because I find you a-peeling
Are you wi-fi? Cause I’m totally feeling a connection.