

This article is an excerpt from the Shortform book guide to "The Fine Art of Small Talk" by Debra Fine. Shortform has the world's best summaries and analyses of books you should be reading.
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Want advice on how to ask someone on a date? What do you do if you get turned down?
Asking someone on a date can be nerve-wracking—especially when you’re afraid of being turned down. Additionally, when planning the date, you should always provide full details rather than trying to surprise them and pick an activity where you can converse in a casual environment.
Here are more tips from The Fine Art of Small Talk on how to ask someone out.
How to Ask Them Out
The purpose of dating, according to Fine, is to learn about each other, discover what it’s like to be around each other, and enjoy each other’s company. In short, you want to know if this is a person you’d enjoy spending some greater portion of your life with. As such, Fine says, plan dates that maximize your ability to interact, converse, and connect. Before you ask someone out, Fine recommends thinking of a few casual dates—activities you’d enjoy engaging in with a friend. Be prepared to provide the full details up front.
(Shortform note: When it comes to planning dates, Fine suggests you prioritize conversing and connecting. However, to really help your partner to open up, it’s arguably more important to prioritize their feeling of safety and comfort. As such, don’t try to surprise your date: Always share the full details when you extend your invitation. Make sure the date is safe and casual; there shouldn’t be anything about the venue or activity that involves danger or threat. Further, be flexible—offering multiple date options allows you to work around your schedules, as well as the possibility that your partner may not be comfortable with your first suggestion. Finally, be understanding: The other person has every right to say “no,” and if you can’t accept that, you’re not ready to date.)
Here’s how to ask someone on a date: When you make the call to arrange the date, Fine says it’s important to remind your potential date of who you are: Refresh their memory of specific things that happened when you met, and tell them what you enjoyed about the time you spent together. Let them know you’d like to connect with them again, and then offer your date idea.
Here’s an example conversation:
- Andrew: “Hi Julia, it’s Andrew; we met at the speed dating event at Barlowe’s last week.”
- Julia: “Oh, hi Andrew, it’s nice to hear from you again!”
- Andrew: “Julia, I really enjoyed hearing about your experience working for the Monterey Bay Aquarium; I’m still chuckling about what you said about penguins.. I was hoping we might get a chance to hang out again sometime soon.”
- Julia: “That would be fun! I’ve been wanting to hear more about your volunteering at the raptor center..”
- Andrew: “Well, would you be interested in joining me for a walk around Bowness Park on Saturday? There’s a little coffee shop there that makes really nice pastries. We could go, say, around ten?”
- Julia: “That sounds great! I’ll text you on Friday afternoon and we can decide where to meet.”

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Like what you just read? Read the rest of the world's best book summary and analysis of Debra Fine's "The Fine Art of Small Talk" at Shortform .
Here's what you'll find in our full The Fine Art of Small Talk summary :
- Why we need small talk and why we shouldn't avoid it
- How to appear confident and engaging in any context
- How to break the ice with strangers and keep the conversation going