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How To Overcome 4 Awkward Dating Situations


Here, four people recall their most embarrassing dating moments — and our etiquette expert offers advice on the best way to handle things, should you find yourself in a similar situation!

By Jen A. Miller

ating can be wonderful, funny and — let’s face it — occasionally awkward at times. And while not every date always goes
Showing grace under pressure is always the proper thing to do.
according to plan, that doesn’t mean you need to bail out when an embarrassing situation does arise.

We shared four awkward real-life dating stories with Diane Gottsman, etiquette expert and owner of The Protocol School of Texas, and asked her advice on what would have been the proper thing to do in each situation. She might not have been able to help our singles out during their awkward dates, but these tips could help you the next time you’re faced with one of your own “oops” moments on your path to finding romance.

Awkward Situation #1: He spilled his drink all over her… twice!
Stacy, 23, from Philadelphia, PA was on her first date with a new guy that started out badly when he accidentally spilled hot coffee all over her. “Thankfully, I had a spare sweatshirt to change into,” she says. But that wasn’t the end of it: “We went off later for drinks; he managed to accidently spill red wine all over my navy jeans,” recounts Stacy.

How they handled it: Stacy simply went to the bathroom and cleaned up as best she could. (The bartender gave her a free drink, too.)

Gottsman’s analysis: “A spill is generally an accident, so the gracious thing for the lady to do would be to make the best of the situation by cleaning up the mess and, whenever possible after a particularly nasty spill, making a detour home to change outfits. If this happens to you, you shouldn’t roll your eyes, get mad and scream about it, or call him out on what just happened. Reacting this way will only make your date feel clumsy (which, honestly, in this case, it he sounds like he was!). Showing grace under pressure is always the proper thing to do.”

Awkward Situation #2: He used the “L” word with his girlfriend too soon
Antoine, a publicist from Minneapolis, MN, let his emotions get the best of him when he blurted out “I love you” unexpectedly: “My girlfriend of just over a month was getting out of my car over the weekend and it just came out of my mouth,” he recalls.

How they handled it: Awkward much? Yes, according to Antoine — but following up that uncomfortable moment with some good communication saved the day. “Thankfully, we were able to talk about it and I told her that, while in fact I do care for her greatly and am very comfortable around her, I’m not ready for us to use the word ‘love’ just yet,” he says.

Gottsman’s analysis: “If someone slips up and says ‘I love you’ and immediately regrets it, the best thing to do is own up to the misstep and not dwell on it for very long by giving
It’s important to set a precedent during the first date.
up too much information after the fact. For example, simply say, ‘I realize that a few minutes ago (or yesterday, etc.) I said that I loved you. I have to apologize and clear the air. I think a great deal of you, but I should not have proclaimed my love — I misspoke. I hope you understand and will forgive my thoughtless remark.’ Period! No more than that is necessary.”

Awkward Situation #3: The movie they picked for their first date made them both uncomfortable
Christina, 30, who works in advertising, was asked out for a typical dinner-and-a-movie date by a guy she met at a mutual friend’s birthday party. “An independent movie festival was going on, and since he was all about supporting independent films, we went to see the one that was currently playing,” she recalls. But the movie wasn’t exactly what either one of them expected — with a plot involving prostitutes, kidnapping and murder, their movie date felt more like a disaster. “It was a really disturbing movie to watch… especially on a first date,” says Christina.

How they handled it: Christina and her date stayed in the theater until the bitter end. (Unfortunately, they never did go out again.)

Gottsman’s analysis: “The right thing to do would have been for one of them to look at the other and say, ‘Wow, this is not what I expected. I’m so sorry, would you like to leave?’ Usually the person who picked the movie should do this, although there is nothing wrong with the other person saying, ‘Hey, this is too much for me — do you mind if we leave and find something else to watch that’s not so bloody or graphic?’ It’s important to set a precedent during the first date if something offends you without being rude or dramatic about it.”

Awkward Situation #4: His date got him confused with someone else
“So many business cards were exchanged over the course of our monthly meeting because we had about a thousand members,” says Drew, 44, an active member on the board of a professional marketing association from Atlanta, GA, explaining how a case of mistaken identity led to his own awkward dating moment. At one of the group’s events, Drew had been flirting with another guy who agreed to go out with him for a coffee date — but their chemistry just wasn’t the same later on when they finally met up with each other. “He seemed distant, so I finally asked him about it,” says Drew. “His reply: ‘Well, I talked to a lot of other people that evening and I didn’t quite realize who you were when you called. I was really hoping it was this other guy I spoke with who was calling me, not you.’”

How they handled it: Drew tried to joke about the situation to ease the tension after his date’s confession.

Gottsman’s analysis: “Drew should be grateful he didn’t actually hook up with this guy! After hearing that his date was disappointed, Drew should have replied, ‘I understand. Sorry for the mix-up; let’s just call it a night.’ The bottom line is that the other guy was very rude for making that comment, and Drew sounds like he took the high road. He shouldn’t take things like that personally; instead, be thankful not to be pursuing a relationship with a guy like that!”


Jen A. Miller is a NJ-based writer whose work has appeared in The New York Times, The Philadelphia Inquirer, Psychology Today, The Washingtonian and Men’s Fitness.
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