How to Ask Someone Out
(… and get an enthusiastic “Yes!”)
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. In fact, asking someone out was the #1 suggestion that appeared today when I started typing in Google. Proof that everyone is struggling:
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 know …
The Quick 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 on 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, 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.