Table of Contents
- Step #1: How to Talk to Anyone
- Step #2: Find Your Diving Board
- Step #3: The Ask
- Step #4: Digital or In-Person?
- Asking Someone Out In-Person:
- Asking Someone Out Over the Phone:
- Asking Someone Out Over Text:
- Asking Someone Out on an Online Dating Website or App:
- Step #5: Consider a Wing Team
- Step #6: Laughter is THE Secret Ingredient for Attraction
- Step #7: Read Nonverbal Cues of Attraction
- Step #8: How to Ask for a Set-Up
- Last Minute Pep-Talk:
Have you ever had to ask someone out? It’s a harrowing, anxiety-filled, awkward experience. And worst of all, no one has ever given us any real guidance on the subject. It’s unlikely anybody ever sat us down in high school and gave us a step-by-step roadmap to dating the same way they taught us algebra.
So it’s no big shock that asking someone out is a big social challenge.
People have a bigger problem with asking someone out than asking for a raise at work.
Let that sink in for a second!
Is asking someone out really that hard?
Not if you follow my easy to use roadmap for asking someone out…
Even if you’ve never done it before.
Even if you’re scared as hell.
Step #1: How to Talk to Anyone
We hate small talk. We hate it so much that we’ll avoid people altogether so we won’t have to deal with the same awful questions:
- “So, what do you do?”
- “Where are you from?”
- “Come here often?”
Ironically, though we hate small talk, we cling to it like a shipwreck victim clings to a life preserver. Why?
Because it’s all we know. And everyone else is doing it, too. So much for our mom asking us, “If all the other kids jumped off a bridge, would you do it too?” Now we know the answer would be: Yes, of course.
Here’s what you can do instead:
- Ask them for advice. “Where’s a good place to eat around here?” “Is it worth signing up at this gym? What’d you like about it?” This is a great way to determine if you share a mutual interest.
- Be playful. “I have an emergency. [Dramatic pause.] I can’t decide whether to order the Caffè Americano or the Caffè Latte. Which do you think I should get?” Bonus: If you’re both at a coffee shop, it’s reasonable to assume the other person is a coffee junkie too and is likely to discuss their favorite drinks with you.
- Be thoughtful. “If you could hop on a ship tomorrow and go anywhere in the world, where would you go?” “If you were a superhero, what would be your superpower?” Much more interesting than asking what their major was in college!
- Ask them for a favor. “Hey, can you hold my jacket for a sec while I grab these drinks?”
- Make a stand (but don’t overdo it). Warning: For advanced students only. This isn’t about being a rude jerk. That said, you’re attractive when you’re passionate about something and have an opinion about it. Avoid religion and politics. Safe topics include movies, music, food and anything else you’d feel comfortable discussing with your grandma. “Texas BBQ is the best, and no one can convince me otherwise.” Say it with a smile so people don’t take you too seriously.
Above all, just start talking. The other person has just as many insecurities as you do. They’ll be grateful you took the plunge and started talking to them first so they didn’t have to go through the agony of taking the initiative themselves.
Step #2: Find Your Diving Board
The easiest way to feel confident asking someone out is to come in prepared. I call this finding your diving board. Before you approach someone, you should know what commonality you both share. In other words, is there a topic, place, hobby, or activity that you can use as a diving board into a date?
The formula you can use to ask someone out is:
- Claim: This is where you bring up a topic or hook that you think you might share.
- Excitement: Next, you want to add the emotion. Is this going to be fun, exciting, adventurous, silly, good…? Make a promise.
- Ask: This is a very simple, direct ask for company. It can be as easy as, “Wanna join?”, “Are you free?”, or “Feel like coming?”
Here are some examples:
- “There’s a wine tasting at Rico’s next week. They have a great selection. Wanna go?”
- “Have you seen the new Batman movie? It has an awesome Rotten Tomatoes rating. We should go!”
- “There’s a new club opening this weekend. The DJ is supposed to be amazing. You should come!”
Step #3: The Ask
Let’s dive a little further into the ask. There are a few things you want to keep in mind before asking someone out:
- Be specific. Vagueness makes people nervous. For example, ask what they’re doing this weekend. Then say, “Would you like to go with me to dinner at Angelo’s on Friday? After dinner, we could catch that concert in the park.” This makes it clear you’re asking them on a date and not a platonic hangout.
- Stay safe. When in doubt, pick a safe activity that’s low commitment for the both of you: coffee, lunch, or dinner. Avoid movies as they prevent you from getting to know each other.
- Be flexible. They may say no … only because they’re busy that weekend or they hate Italian food. They may make a new suggestion, which is great news for you because compromise means they want to make this work.
- Be cool and casual. You’re not a salesperson, and you’re not closing a deal. If the person says yes, smile and say great. Never be pushy or make them uncomfortable.
Step #4: Digital or In-Person?
Building confidence, talking to people, gaining their trust? Those things take time and practice. Here’s the good news: asking someone out only takes a few seconds! The question is: Do you ask someone out in person, through text, online, through email, on social media, on a dating app…?
I think this is an essential part of your success. You want to pick the method that makes YOU most comfortable. Of course, I will always recommend in person because you can easily read their body language and gauge how they’re taking it, modify your behavior accordingly, and either quickly redirect or run.
We also like seeing people’s faces because it puts us at ease. A smile makes us smile, and body language fosters empathy and a sense of feeling connected to another person. Which as you can imagine works in your favor big time when asking someone out.
Plus, asking in person makes you look brave and serves as good practice for the date! If you can’t handle talking to them in person, how can you handle meeting for coffee?
However, there is also a downside to in person: There’s no hiding.
If you know that you will be too nervous to use confident body language or take in their cues, then phone or email might be a better option for you. So let’s review the options and tips.
Asking Someone Out In-Person:
- Smile and make eye contact, but don’t stare. If you find yourself getting nervous, briefly glance at their shoulder or another part of their face.
Asking Someone Out Over the Phone:
- Let them know you are going to give them a call with a heads-up text or email. This increases the chances they will pick up. Or if they push back on the phone call, you know that they might not be ready to be asked out.
- Whatever you do, never leave a voicemail or a note asking someone out. You have no way of knowing whether they got the message or not, and you lose the element of warmth that comes from asking them directly.
Asking Someone Out Over Text:
Let’s get something out of the way: I like texting to build suspense and get to know each other, BUT too much texting is dangerous because it sets a precedent. You don’t want the potential relationship to hinge on texting instead of face-to-face communication. And you definitely don’t want to finally show up to a date and awkwardly realize the rapport you had over text doesn’t translate to real life.
Texts should be primarily used for two things:
- Spiking interest. Be flirty and fun. “You have an amazing voice. I bet you’re a real crowd pleaser at karaoke.” Or take an opposite tack: “I bet you can’t beat me at a karaoke match ;)” Now you’ve issued them a playful challenge which naturally segues into an invitation.
- Making plans. Texts are great for logistics and check-ins. They can also be used to gauge interest.
- Whatever you do, never ever send a text like, “I’m bored. What are you doing?” Nobody wants to babysit you. Be interesting and focus on having a great life. This way the other person feels like they won the damn lottery to get to be a part of it.
Asking Someone Out on an Online Dating Website or App:
Ah, online dating. Welcome to the 21st century. A few ground rules:
- Don’t be lazy. The goal is to meet in person and go on actual dates, not sit at home messaging each other back and forth while you watch Netflix. It’s easy to get lulled into a false sense that you’re getting somewhere when all you’re doing is chatting online with a bunch of strangers.
- Don’t let it be your only method. The upside of online dating is you can search for people by any filter including mutual interests. The downside is you cut yourself off from the spontaneity of real life; you never know when you’ll run into a great match at a friend’s party or your favorite coffee shop. Use online dating in conjunction with other methods, not as your sole method.
- Don’t wait too long to make your move. After two or three messages, you have a sense of the other person’s interest. Don’t say anything self-defeating like, “I don’t suppose you’d like to meet up, would you?”
Focus on getting little yesses from the other person: “I think talking in person is a better way of getting to know someone than email.” If you can get a yes on topics you know they’ll agree with, they’re more likely to say yes to meeting up with you.
Suggest something that’s easy and a low investment, like getting a coffee. You don’t have mutual friends to attest to how wonderful you are, and this person doesn’t even know what your voice sounds like. You’re a total stranger! By making this easy for them, you’re not putting any pressure on them. This gives you major brownie points in their eyes.
Once the other person confirms, give them two options to choose from (i.e. Friday night or Saturday afternoon). This shows respect for their time and gets them more engaged in the conversation.
Finally, send them your phone number “just in case something comes up” and ask for theirs as well. (Note: Obviously, do this only if you feel comfortable.)
Step #5: Consider a Wing Team
Don’t feel like you have to go out for the first time alone—especially if you are asking someone you don’t know very well. Go on double or group dates. It’s less pressure for everyone involved, and you won’t have to worry about awkward lulls in conversation with other people around you.
Stumped for group date ideas? Here’s a few:
- Go the beach. Barbecue, have a cookout, and play sports.
- Host your own Iron Chef. Everybody has to cook dinner and dessert using a crazy ingredient, then the group picks the winners.
- Get tickets to your favorite sports game.
- laser tag
- mini golf
- play pool
- Have a game night. Everybody brings their favorite game; make sure to have good snacks on hand.
- Have a picnic.
- The museum: most museums are cheap, and some are donation only.
- Bike riding—if you don’t have a bike, check Craigslist for good deals. Some cities also have cheap bike rentals.
- Go to a local fair or carnival.
- Host a movie marathon. Bonus: test each other on movie trivia while you watch.
- Have a video game competition.
- Volunteer. For those who like philanthropy, sign up at the local food kitchen or somewhere else that needs a helping hand.
You’re only limited by your imagination and people’s interests!
Step #6: Laughter is THE Secret Ingredient for Attraction
Before you can find love, you should aim for a much easier target: humor!
According to Professor Jeffrey Hall at the University of Kansas, sharing a laugh together is a strong indicator you’re interested in each other. Men especially use humor to gauge a woman’s romantic interest. And Hall’s study found that women were in fact more likely to laugh at men’s jokes to show they were interested.
Humor indicates you’re a warm and fun person. And who doesn’t love someone who’s warm and fun? It also deepens the relationship, so you’ll have a stronger bond that can last years once the initial flurries of attraction wear off.
And because humor is a safe method for testing mutual interest, you don’t risk overt rejection. You can casually feel the person out and segue into asking for a date in a way that feels natural. You smooth talker, you.
Now you’re probably thinking, “But I don’t know how to be funny!” Look, we’re not talking about doing stand up comedy. In fact, Andrew Tarvin at Humor That Works says humor is subtle and requires very little effort. It can be as simple as a smile, a turn of phrase, a play on words, or making a funny face. Even then, it’s not so much about being funny as being fun, and making people feel welcomed. “If you think fun, you think positive and you think inclusive,” Tarvin says, “you’re well on your way.”
You know who’s super funny? Children. They’re always smiling, laughing, and fun to be around. They think everything around them is hilarious, and they let you know it. Are they doing stand up like Chris Rock or Louis CK? Of course not! Kids are too busy pouring cereal down their pants and smashing bananas on their foreheads.
You can take away two key lessons here:
- First, kids don’t worry about being funny. They’re focused on having fun.
- Second, kids are curious about everything and love to share their experiences with the people around them.
This kind of warmth and openness works. How many times have you seen a kid thaw even the most serious adult? Point being, you don’t need to be a comedian to make humor work for you. Focus first on being warm and inviting. You’re at a dinner, not a deposition. If you remember nothing else, remember this:
- Stop thinking about what you’re going to say before you say it. You’ll come across as nervous and unconfident. Humor comes from spontaneity and fun, not memorizing one-liners.
- Really listen to what the other person is saying. You’ll respond quicker and look engaged. Being attentive and smiling will take you farther than trying to be the next Louis CK.
Okay okay, but what if you really want to nail your comedy skills and wow everyone in a room like a pro?
Then you need to listen to my friend David Nihill. He went from being mortally terrified of public speaking to doing stand-up comedy at sold out shows, and winning storytelling awards … and he did it in just one year. He wrote a guest post for us on 8 Ways to be More Funny. Check it out here.
Step #7: Read Nonverbal Cues of Attraction
Want to know if someone is into you? Pay more attention to body language and flirtation. Men and women do this very differently:
For example, women show their desirability by tilting their head to expose their neck (a prime erogenous zone). Men stand up straight, square the shoulders, plant their feet slightly more than shoulder width apart, and display their hands.
As you get better at reading and responding to body language, you’ll notice people finding you more charismatic and responding to you better. “Fake it till you make it” is a tired and overused phrase. People sense desperation and inauthenticity wafting off you like a bonfire. Faking confidence won’t mask that.
So how do you project confidence when you’re shaking in your shoes?
Researchers at Ohio State found that good posture gave people more confidence in their thoughts, and they rated themselves more positively versus when they were slumped over.
“People assume their confidence is coming from their own thoughts,” said Richard Petty, co-author of the study and professor of psychology at Ohio State. “They don’t realize their posture is affecting how much they believe in what they’re thinking.”
In other words, you can’t think yourself better … but it is possible to use confident body language to trick your brain into believing you really ARE better. A quick and simple solution to this is something called Power Body Language.
Power Body Language is a way of standing and expressing yourself that not only makes you more influential with other people (in a way that’s totally authentic and honest), but also makes you feel more confident too.
Confidence not only ensures you’ll actually ask the person out; a University of California study found that students consistently ranked people who spoke up often as more intelligent than they really were. So confidence literally makes people think you’re smart and a leader! All good traits to have when you’re trying to put your best foot forward and impress someone.
If you’re still nervous about asking someone out, consider that we spend the majority of our lives worrying too much about ourselves, and we don’t pay nearly as much attention to other people’s perceived flaws.
In other words, whatever you’re self-conscious about, the other person’s probably too busy feeling self-conscious to notice. So cut yourself some slack. It’s likely the other person will be flattered you asked them out (or impressed, because the very idea makes them nervous too).
Step #8: How to Ask for a Set-Up
Remember that old story about Cyrano de Bergerac?
Trust me, you’ve heard it before, even if you don’t recognize the name. It’s about a guy wooing a girl … and one of his friends is hiding under the balcony feeding him lines. Nothing worth doing is ever done solo, so why should dating be any different?
Your friends can play matchmaker for you. They’ll even be thrilled to do it, because who doesn’t love seeing two people hit it off? Plus it makes them look good when their recommendation is a hit.
Did you ever hear the story about the supermodel and the rockstar who couldn’t find a date? It’s true. Iman and David Bowie got hooked up by their mutual hairstylist after complaining to him that they were unlucky in love. They were happily married for over twenty years. Goes to show you even famous people need matchmaking help from a friend sometimes.
If you don’t have a particular person in mind to ask out, but you’re actively looking, ask your friends what interesting friends of theirs you should meet.
Note how you’re not outright asking for matchmaking services. Why?
- Because many people aren’t good matchmakers, especially off the top of their head.
- Because people don’t like being put on the spot … and the paradox of choice suggests that if someone has to pick ONE person out of everyone they know, they’ll feel paralyzed and won’t make ANY choice.
So instead say:
“Hey, I’m looking to make new friends and you know interesting people. Who do you know that is super cool that I should meet?”
Two reasons this works:
First, they’re more likely to offer suggestions since the pressure’s off about being perfect and hooking you up with your one true love. That’s like asking someone to hit a Grand Slam on their first day of Little League practice.
Second, you’re still very specific with this request. You’re not looking for new business contacts. You’re looking for casual relationships you can explore to see if there’s something worth pursuing.
Dating is a numbers game and much of your success in asking people out requires simply connecting with a lot of folks. Your friends have classmates, coworkers, neighbors, friends of friends, a favorite barista… the list goes on. They may even arrange a personal intro if you ask.
And if they don’t have a recommendation ready for you? No problem. They’ll know about social events where people with your shared interests are hanging out.
A huge mistake people often make when meeting someone is they let their hopes get dashed when they don’t see any initial chemistry. So they give up on them. This drives me nuts! This person might be friends with your future significant other! Why give up so quickly before they can introduce you?!
For example, if you’re a woman looking for a man, and you make friends with a guy but there’s no spark, you may think why bother talking to him again?
But this guy knows a ton of other guys! Imagine if you met one new guy a week. After a year, that’s 52 men, plus all their friends and cousins and co-workers. How quickly do you think you’d be introduced to a guy who’s right for you?
So keep making friends, and don’t hesitate to ask them for help. Remember, you’re practicing your dating skills by meeting people, even in casual social situations.
This way when you finally meet someone you’d like to ask out, it’ll feel natural. You’ve practiced cracking jokes, you’ve practiced Power Body Language, and you’ve practiced meeting tons of people. You’re ready for the playoffs.
Last Minute Pep-Talk:
A few more things I want you to keep in mind before your big ask:
- Pick 3 of my 13 Great First Date Questions … to have awesome conversation once you are actually on the date.
- Rejection won’t kill you (even if it feels like it will).
- Perfectionism is ugly. It makes us think rejection is the ultimate failure. It makes us worry that we have to find our soulmate or else we’ll never be happy.
- People may turn us down for a lot of reasons, many of which aren’t personal. They’re in a relationship, they’re not dating right now, we’re the wrong gender for them, their dog died, they’re just not feeling it today, whatever.
- There are a million reasons someone may not bite. It’s not about your value as a person; dating is about finding the right fit.
- The more people you talk to and practice this with, the easier it becomes, and the less attached you’ll become to getting a yes.
- Every person you meet and practice with brings you one step closer to getting a yes from the right person. Asking people out becomes more about testing to see what works and who you want, not a black mark against your self-worth.
- Let the person know there are no hard feelings if they say no. You never want someone to feel obligated or put on the spot. Give them an easy out. “Well, it was worth a try! Thanks anyway!”
- It’s flattering to be desired. Many people will feel tickled that you took the time to ask them out. If someone makes you feel bad for having asked them out, thank your lucky stars that you dodged a bullet.
- There’s a great Lyfe Jennings lyric: “Don’t be a nickel out here lookin’ for a dime.” It’s a good mantra for dating. Why should someone want to be with us? Are we acting like the partner we want to have?
Practice. Practice. Practice.
Professional athletes don’t wait until the big game to start training. They’re practicing all the time. Same goes for dating. Every person you meet brings you one step closer to the partner of your dreams.
My sincere hope is that this marks the beginning of a fruitful dating life for you, and that you never stop honing your skills.