The Art Of Date-Night Conversation

Our dating etiquette experts teach you how to chat up anyone—especially that lovely creature sitting across the table from you.
By Phineas Mollod and Jason Tesauro

hen it comes to wooing someone, intimate cafés, jazz clubs, ballgames and park promenades are main ingredients. Conversation, however, is the spice that determines if you’re a bland dish of blah or a colorful plate of wonder. Everyone has their own brand of charm, but without some conversational panache, a first date feels pretty much like a corporate Q&A — a dry exchange of biographical info. To generate cool chat, we’ve outlined simple tips to keep talk flowing:

Review Your Hot Topics
A date shouldn’t be scripted or reduced to
Prep by coming up with snappy answers for likely questions.
crib notes, but to warm up the charisma, reserve ten minutes for prep. Like chopping herbs and veggies before heating the frying pan, readying your brain for a sumptuous dinner of dialogue helps the date simmer more smoothly. As you make your way to the rendezvous, run through a conversational refresher of funny stories, noteworthy news oddities and other talking points to fuel chitchat or relight the pilot if sparks sputter. Then, silently ask yourself these high-probability questions and outline some snappy answers: “What’s new?” or “What do you do?” and if this was the culmination of online mating, “What drew you to my profile?”

Chat Yourself Up
Portray yourself as the winning lover and companion by covering dynamic topics that separate you from herds of dull souls. Creative leanings, pet causes and foreign adventures paint you as fun-loving, socially active and a tad sexy, so tell your date all about them. A vivacious personality projects sex appeal, while a limp list of credentials and professional memberships suggests unimaginative pillow talk later on.

Better Banter
Good: Referencing information aired in previous email and phone calls (“You mentioned that you hawked pretzels at Raiders games after high school”). Bad: Rambling tales of collegiate mischief and job ennui are yawn-inducing, as are stony silences. Also, premature EP (earning potential) and matrimony-feelers feel like the preapproval process before qualifying for a mortgage.

Even shy types can spur on a bubbly exchange. Remember what mom said: Don’t be interesting, be interested. Instead of hogging the mike, pass it to your date. And when you’re on the clock, put your banter to better use. For instance, the standard 20 questions reveal home towns, relationship history, criminal priors and favored kissing techniques, but it should advance naturally during energetic conversation, not one-by-one from a clipboard checklist.

Edge Your Way to Improv
When both of you are completely comfortable, take
Remember, don’t be interesting; be interested.
off the kid gloves. Those with a Dennis Miller streak might throw in a little levity and over-the-top humor with a well-placed rant. Take the stage for a spontaneous bit on some Seinfeld-ian pet peeve — the scourge of pigeons, the evils of processed beef jerky, or your local Soup Nazi. Overdo this strategy too early or too often, however, and you will be seen as either a wild card or a cynical (and soon-to-be-dateless) weirdo.

Try Asking These Five Questions
You know those job-interview questions you despise? Fear not, that battery of queries can be refashioned, with wit and a smile, into clever conversation starters when other techniques fail to get the chatter cooking:

Old: “Where do you see yourself in five years?”
New: “What are some of your crazy dreams and lottery-winning fantasies?”

Old: “What are your strengths?”
New: “After quitting time, which passions and pursuits keep you out late? How do you relax on the weekends?”

Old: “Why did you apply for this job?”
New: “Before we both went for the same dryer at the laundromat, who noticed
who first?”

Old: “How did you hear about our company?”
New: “I’m glad Tia and Gino played matchmaker. What was it they said that piqued your interest?”

Old: “I’ve told you everything you need to know. Do you have any more questions?”
New: “Well, I’ve admitted I am a tennis fanatic and amateur painter who occasionally blows extra cash at the dog track. Now that you know my secrets, what’s one of yours?”

Few women can resist offering up a confession of their own under those circumstances.

Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train with his wife and daughter in New York. Jason Tesauro pushes pen and ink by day and leads the lifestyle seminar series by night, ne'er far from his sweetheart and a Brady Bunch houseful 'o tots in Virginia. Together they are the authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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