How to Win with First-Date Conversations: What’s Your Headline?


first date tipsWe all know the rules of first-date conversations. You’re not supposed to talk about sex, exes or politics. As a friend once told me, “You’re one dumb outburst away from never seeing this person again.” Sounds easy, right? Some people say first dates might even be fun.

Not so fast. You have bigger responsibilities than simply avoiding offending or boring someone as you happily sip your IPA. You need to be mindful of the how the other person will remember you. I’m not talking about bringing a list of talking points that you review in the bathroom, then dash out and say, “Did I mention I like to laugh?” You need to think about what your date would say about you if a friend asked, “So how did it go?”

Your date will likely summarize you in a sentence or two. “I met this nurse who just moved here from Montana. She’s really into biking and makes her own granola bars. She didn’t talk much, though.” Or “I just had a great date with a divorced dad who told me funny stories about camping with his kids. He’s a big movie buff and has a huge DVD collection.”

Yes, this is unfair. We are complex human beings forced to reduce our very essence to a paragraph in a profile or a couple minutes of conversation. The problem is that when we’re trying to get to know someone and make a quick decision whether we want to see that person again, we don’t remember nuances. We remember headlines.

Here are some tips on making sure yours are memorable.

1) Know Your Brand

You’ve already decided in your profile what you’re about and what mix of professions, geography, hobbies, relationship history, political affiliations and opinions about online dating you want to emphasize. Did you write in your first sentence that you’re a “single mom who loves to garden” or did you play up that you’re a “native New Yorker and passionate Yankees fan”? Or maybe you said you’re a “Houston transplant who works as a high school math teacher.”

These characteristics make up your base brand. Sometimes you can’t determine how others will see you. Perhaps your date just told his co-worker he had to leave early to go meet a “blonde lawyer.” But you can tinker with your identity to shape those early conversations. For example, several years ago when I wrote that I was “a magazine writer from San Diego,” my dates often asked, “Are you like Carrie Bradshaw or something? Are you going to write about our date?” (Yes, because my editor is going to love this material!) Or they would ask how I could be so foolish to leave a beautiful place like San Diego for dirty cold New York.

Since I hated both those topics, I changed my profile to emphasize my love of the outdoors and my idea of a perfect Sunday evening. Guess what? The conversations shifted to the positive qualities I wanted to emphasize. I got to talk about how it felt to be on a sailboat when the water became glittery at sunset – rather than reassure him that I wasn’t going to tweet our date.

2) Select Your Stories

Be mindful that what you say isn’t always what people hear, especially since they don’t have any context to know what you really mean. Don’t complain about your overbearing boss who keeps you late at the office most nights to a date who’s wondering if you’ll be available to get together during the week. You don’t want your date’s debrief to his mom to be “workaholic who likes Mexican food.” You could tell a funny story about your grandmother’s mean cat and risk your date concluding that you’re not a “cat person.” (Actually, I would want to hear that story, but it might help to add, “I just want to be clear I love cats.”)

You don’t have to monitor every word that comes out of your mouth. Just try to be extra positive and enthusiastic about your life at least during those first few exchanges. It might even help to remind yourself in advance of your best attributes and what you’d like to play up during the date. (You’re great at making campfires. You make colorful and healthy summer salads. You love to laugh.) You’re not following a script, just planting seeds of conversation … and reasons for a second date.

About the Author:

Sarah Elizabeth Richards is a journalist and the author of Motherhood, Rescheduled: The New Frontier of Egg Freezing and the Women Who Tried It. Her writing has appeared in The New York Times, The Wall Street Journal, Marie Claire, Elle, Cosmopolitan, Slate and Salon.

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