The goal of the first handful of dates is to establish common ground and figure out whether the two people involved possibly have a future together. But none of that can happen if the woman you're out with is shy or shuts you out. So, your primary duty is to draw out your dinner-mate's story-without any too harsh tactics. You don't want to sound as if you're interviewing her for a job, nor like you're grilling her, police-drama-style. You need to step up your conversational game, show off your natural charm…and nimbly encourage her to reveal more of herself. Follow this advice to do just that. And remember, the more you share, the more quickly the two of you will feel connected.
1. Prep Properly
Want to ensure loose lips come date night? Start before the date. Clever banter and pulse-quickening flirtation don't have to wait for Saturday. Doing some leg work via phone and email creates a culture of exchange beforehand, priming the pump so that by dinnertime, delving in should be easy.
2. Ooh & A-ha
Exciting interjections urge her on. Be quick with a laugh and calls of "No way!" and "Get out of town" and "That's crazy!" These exclamations are conversational kindling. Let her know that you're into the tale she's telling, and she'll be encouraged to share further. The better you are at responding with genuine interest, the more likely she'll let down her guard and grant you an extra level of security clearance.
3. Nix the One-Upmanship
"Oh, yeah? You think that's funny? Then let me tell you about the time..." Statements like these only serve to lift your ego and render her anecdote irrelevant. If you must follow her story with one of your own, at least give some credit: "What a story. That reminds me of a similar thing that happened to me. It's not as wild as your spring break episode, but once upon a time…" This kind of follow-the-leader shows that you're listening and that you have an awful lot in common.
4. Ask Open-Ended Questions
Yes or no questions are fine for lie-detector tests and cross-examinations, but they won't help your coffee chat gain any traction. Instead of "Do you still kayak?" ask "What's your favorite part about being in white water?" The key to verbal interplay is the natural back and forth, not just a trade of monologues or rat-a-tat-tat of rapid fire yes/no questions that get you nowhere ("Have any brothers or sisters?" "Do you like dogs?" "Having fun?" and so forth lead to, "Check, please!").
5. Follow-Up, and Branch Out
If it's taken her the entire drinks and starters course to convey "What I did last summer," don't just give it a perfunctory shrug and move on. This is your chance to mine her memory banks for rich details and the kind of personal data that fills in the blanks about her development and inner life. Try: "What's next for you?" or "How are you different a year later?" or "What did you learn?" These are all excellent questions that turn the tables, inviting her to take a further step toward trust and confidence.
6. Set the Pace
In the Tour de France, the leader wears a yellow jersey. On a date, if that prodigious IM'er turns out to be a shy talker, open her up by being forthcoming yourself. Reveal something and then say, "Now there I've gone and told you something personal." Some daring Romeos might take this as an opportunity to say: "Your turn to tell me a secret," yet tread carefully-a gent knows when to be bold and when not to press. And once you're versed in these date-night tactics-of course, you're a gentleman!
Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested 6 train and wooing his live-in New York femme. Jason Tesauro toils at a vineyard by day and by night pushes pen and ink while celebrating 5 years of wedded-ness with his everlasting one-night-stand. 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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