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Oops! How To Recover From Dating Disasters

Did you accidentally spill wine on your date, stick your foot in your mouth, or do something else you regret? Here’s how to recover from any gaffe.

By Phineas Mollod and Jason Tesauro

obody’s perfect. Even Casanova now and again misspoke or dropped an errant oyster shell onto a Venetian consort’s lap. So it stands to reason that during any date, the average person will commit some minor mishap and that it’s probably not fatal. While a quick “I’m sorry” works for many gaffes, other more serious transgressions require a more in-depth fix-it strategy. Here, a trouble-shooting manual for any faux-pas, no matter how mortifying.

Bad venue
Sometimes, a bout of awkwardness is caused by the vibe-killing
Stuck in an awkward silence? Acknowledging it can put you both at ease.
atmosphere of the room. But why let a café choice reflect your personality poorly? Laugh, and bond over the dreadful service, blaring speakers, or rotten tunes: “I guess I’m on probation now… you can pick the next place” or “Who knew? It got a great review!” Bounce back easily with a spontaneous change of plan: “Let’s switch gears and blow this joint. I know a better place three blocks away, or there’s always bowling!”

Foot-in-mouth mistakes
This malady affects both verbal clods and the most adept dater. Before the evening gets rolling, nervousness can make something untoward fly out your mouth. First aid in this case depends on the severity of the gaffe. For a simple oops that isn’t too personal, like a slur against cats, a simple change of subject will do. Or, at most, follow with a quick apology and push the conversation forward (“Ever since my childhood feline Heathcliff scratched my nose, I’ve hated cats… tell me something to change my mind…”). If your offense is on the heavier end (an insult to her alma mater, career path, or a beloved family member), jump in with a substantive apology (“I’m awfully sorry, forgive me, that didn’t come out quite right”) and follow up with one at the end of the date to show you meant it. But otherwise, don’t mention the misstep again and again. A date is a 2- or 3-hour audition; keep apologizing, and those constant reminders make for a cut that won’t heal.

Awkward silences
There is a break in the action during every date, but sometimes, momentum sputters and the silence becomes weighty, with each party either waiting for the other to begin or chattering about anything just to fill the void. The first inclination after the third long pause is to excuse yourself to the restroom. Stay put. Leaving an ice-cold table exacerbates the tension, causing both parties to rehearse something to say for your return in two minutes. Before pulling the restroom reset, take the initiative to re-establish a modicum of rapport and buy some precious chitchat (e.g., talk about the menu or wine, comment on wacky patrons at the bar). Or, fall back on corny humor: “You know, sociologists say there’s is a lull in conversation approximately every 22 minutes… I guess we’re good for around the next half hour then?”). In any case, never utter, “Sorry, I’m just tired and a little out of it.” Translation: “I’m inattentive. You’re boring. Why are we here?”

General clumsiness
Oops, there goes the red wine onto her rather expensive blouse… but skip the crazy contrition. After procuring club soda, offer to foot the dry cleaning bill and then turn your clumsiness into something endearing, an inside joke. You’ll know there’s attraction cooking if this humorous strategy works. As a capper, offer up a winning anecdote about a similar disaster. Though, if it’s a personal story, couch it as if it happened to a “friend of mine” and tweak the ending (“After my
If the place you picked is too loud, crowded, or boring, suggest switching venues.
‘friend’ Gina knocked over the ice bucket into his lap, they fell in love that night…”) since no one wants to date a career klutz.

Too much vice
If you utter, “Hey, I ordered two shots of tequila for us while you were gone” or “Hey, let’s sneak outside for a smoke?” and get met with an “Um… I don’t do that,” we feel your pain. To avoid these scenarios, always play follow the leader in the vice department and avoid suggesting naughty habits until your date’s demonstrated some proficiency at it. In general, most people are tolerant of a little excess, so it’s not a critical gaffe. A simple response suffices, maybe with a return query that leads to intimate disclosures: “Sorry, I got carried away,” or “Once in a while I bum a smoke while on the town. Do you have any bad habits you’d care to confess?”

Untoward affections
When you feel amorous toward your date, it’s easy to get a little too touchy-feely for that person’s tastes—and while this mishap usually affects men, women should also take note. If you ever end up having your hands nudged (or slapped) away during a sojourn into someone else’s space, here’s how to handle it. First, characterize the rebuff:
Playful push-away (translation: “It’s OK, but bad timing.”): Some people don’t fancy being kissed in public or are coy by nature. If you’re sensing attraction, a rejection might signal poor timing, not an absolute no-go. Be patient and extra cognizant of your date’s gestures and verbal cues. Look for something more than the whiff of green light which led you on your first misguided quest. Instead of withdrawing completely, which may inadvertently show you’re no longer interested, downgrade to lesser affections such as handholding or whatever your current security clearance allows.
Absolute red light (translation: “No way José.”): Wandering paws slapped unceremoniously off tensed thighs, followed by a reproachful glare = hands off. After this transgression, retreat and apologize. Your date may offer you a reason for the snub, or the ultimate answer that he or she is just not into you. But there’s an upside to even that scenario: Now you no longer have to waste your time with “When can I see you again?” emails or text messages the next day. See? Even gaffes have their upside:
If you two aren’t on solid ground to begin with, a small mishap can tip the scales toward “no thanks.” But if you’re truly meant to be, you can do no wrong with these smooth recovery strategies.


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 MGAffairs.com 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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