Men - First-Date Etiquette, Explained

First dates can be a dicey time: Do you greet a woman with a handshake or a kiss? Do you hold the door for her? Let our pair of savvy experts answer these questions and more. Prepare to charm!

by Phineas Mollod and Jason Tesauro

n today’s world of anonymous email and to-the-point voicemail messages, the art of courting a woman often falls by the wayside. Which is why we — experts on modern etiquette and savvy-suitor skills — would like to provide a first-date manners brushup. Not merely trotted out for holidays, manners are more than stuffy rules ingrained from many a granny’s rap on your adolescent knuckles. They’ll put your date at ease, charm her, and convey your affection — all the while boosting your own confidence. So, for your wooing pleasure, we’ve compiled some first-date dictates to speed the way from IM’d emoticons to candlelit sweet nothings.

First-date dictate #1: Dress with finesse
Lead with a swift kiss: Dates that begin with a cold, prudish handshake are doomed from the start.
Put more than a moment’s thought into your choice of first-date attire. Simplicity and sophistication should rule. What’s proper? Neither your Sunday best nor your most casual Friday garb, but rather something pulled from the cleaners, or at least the topmost layer of the hamper. Also worth a mention: If you accessorize to reflect your every interest, you can look like the decorated hood of a NASCAR racer. From your collection of LIVESTRONG yellow wristbands, boldly patterned ties and quirky socks, pick one — and only one — attention-grabbing item before going out.

First-date dictate #2: Perfect the proper greeting
When you pick your date up (much more gentlemanly than having her meet you at a given restaurant), it helps to have flowers in hand. Greet her with a warm, ever-so-slightly lingering kiss on the cheek and proffer a sincere compliment. Try “You’re even lovelier in person” if you’ve met online; “You’re even lovelier than I remembered” if you met in person. If the word “lovely” doesn’t trip off your tongue, try “cute” — the goal here is to say something flattering and sincere. And, yes, we did say to lead with a swift kiss. Dates that begin with a cold, prudish handshake are doomed from the start. This isn’t a business meeting, even if you do want to ruffle through her papers.

Note: Not everyone is touchy-feely enough for a sweeping Hollywood embrace. Train your bachelor eye to decode body language: Is your date recoiling with tensely crossed arms, or looking skittish? If initial chemistry is lukewarm, start slowly and simmer; don’t be pushy with busy paws and probing questions. When the temperature is hotter, capitalize on a live wire with enthusiasm as you unleash a battery of smiles, edgy banter and tender touches across the table.

First-date dictate #3: Charm her with a bit of classic etiquette
Does your date secretly wish you wouldn’t hold the door for her or let her order first? Come now. Do you really need to ask? Revisit some Amy Vanderbilt mandates: Do hold the door, yield
Instead of silently burying your head in a menu, focus on the main dish of the evening… your date.
the seat with the better view in the restaurant and, for Pete’s sake, insist that she have the last yummy bite of dessert. Also, stand when she leaves the table and escort her down the street so that you’re nearest the curb — shielding her from such calamities as bus-sprayed puddles. Nowadays, dating is like job hunting, and a gracious sense of manners is a bonus skill that will increase your curb appeal. (Though beware: Do keep your actions subtle. Overdoing the chivalry routine — say, finding yourself half-bowing as you hold the door for her — will only make you appear to be a phony who’s best suited to chirping “Yes, milady” at the Medieval Festival’s human chess board.)

Convinced you’re not the manners type? Let us put it this way: After suffering through a long week of loud-mouthed bosses and messy roommates, what modern lady wouldn’t welcome some special treatment? Especially given the post-grunge casualness of today’s society, manners stand out… and can melt her heart.

First-date dictate #4: Order with panache
Ordering isn’t just the utility of requesting food, but a time to test plate-sharing preferences and taste-bud adventurousness. Instead of silently burying your head in a menu, focus on the main dish of the evening… your date. If the server returns while you two are just getting warmed up, don’t break the momentum — take command of some never-fail appetizers: “We’re still looking, but please bring the spring rolls while we decide.” While ordering entrees for another is a tad forward, get a sense of her flavors; any opportunity to glean personality clues shouldn’t be missed. After suggesting a Chianti Reserva, do you get a snappy retort about her Tuscan semester abroad, or a blank stare? If the latter, chime in with why it’s one of your favorites — and why you think she may like it too. Since no one is a mind-reader, avoid iffy statements that say nothing (“Sangria sounds okay… I guess”). Rather, accentuate the positives (“I love sushi!”), and voice negatives (“Mussels — never a favorite of mine”). Standing by convictions (no, not the larcenous kind) helps identify common ground while uncovering curious contrasts that can stimulate conversation.

First-date dictate #4: Bid her goodnight in grand style
If the night was a flop, a quick finish with a polite handshake or brief hug is expected, perhaps with great relief. Be simple (“I had a nice evening, thank you. Good night.”). Never make false promises for the sake of propriety (“Let’s do this again…um, I’ll call you.”).

But let’s be optimistic and now focus on a truly delightful night. Don’t sully it with an awkward close or last-second lobby for a slobbery kiss. Your first pitch of woo shouldn’t be volleyed just as she’s unhitching her seat belt or fumbling for apartment keys. In fact, the post-dessert stroll is a fine time for romantic hand-holding. As for the final parting, marry thoughtful words (“What a marvelous time. I’d love to see you and your sweet smile again.”) and actions. By actions, we certainly don’t mean a cold, platonic hug — that’s best left for crotchety aunts and the like. A successful first date is best capped off with a lip-to-lip smooch that neither lingers too long nor leaves too soon. Then, lean back and offer breathing room. If an encore is desired, body language will be crystal clear; otherwise, bid good evening and march away confidently… there will be a next time.

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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