How to Handle Life's Top "What I Should Have Said" Moments

Photo: ThinkstockBy Leigh Newman

1. The situation: You're on a second date with a smart, funny guy. But his last 20 out of 21 sentences have been wisecracks or clever comments. By the entrée, you know this isn't a match. You're looking for someone slower, more relaxed, somebody who can be quiet with you. Spending time with him has not been awful. If it had been, you wouldn't be in this situation, because it would have been obvious to both of you on the first date that you two should not see each other again. But as it is, you ate another dinner, you laughed, you found out you both fear live lobsters and love chocolate-dipped cones. It's all perfectly endurable. But when he leans in to ask for a third date, how do you make it clear that this isn't possible--without being rude?

The response:
"Tonight was wonderful. But I don't feel like we're a shidduch."

Certain, very well-meaning pals will urge you to explain what you like about this guy and what you don't. But men, like many of us, don't need a dissection of their best and worst qualities --most especially at such a moment of open vulnerability. Certain other very well-meaning pals will urge you to identify some flaw in yourself--as if you need to find something wrong with you in order to justify a lack of desire or commitment.

But bringing up shidduch--the Hebrew word for engagement or "match"--focuses your argument on your common connection. What you're saying is: You two aren't suited to each other. Rather than he's not suited to you or you're not suited to him. Those of the Jewish persuasion (fluent in Hebrew) will understand this sentence in a flash. Those of us not of the religion (me!) may require some explanation. Regardless, mentioning the unfeasibility of this particular "match" may just cause you to consider what you are looking for from long-term love--on your next dates, with other people.

RELATED: 11 Ways to Keep the Faith (No Matter What Happens)

2. The situation: You work at an online pizza-delivery company. Your boss, the founder, strolls into your office and describes the new plan she's just come up with. From now on, the website will also sell beer, salad, ice cream and--why the heck not, every family wants one on Friday night--puppies. In fact, she wants to kick all this off by the end of the fiscal quarter.

The response:
"I wish I had thought of that! But are you worried whether we'll have enough time to make that kind of totally groundbreaking change?"

Your boss is your boss--and even if she's deluded at this moment, she's got a dream. The dream may be in that shiny, new, everything-is-perfect-and-possible phase, but you don't need to be the one that says, "That is a horrible idea," because, sorry my dear, nobody loves a dream killer.

Instead, asking her if she's worried about the time frame puts the responsibility for addressing any problems on her, not you--avoiding the usual "I'm worried that..." or "My only worry is that..." This way, she can fret about the logistics (including the one that seems most problematic to you) and, ultimately, realize that she can feasibly expand into the beer, salad, dessert business by the end of the quarter, but should wait to launch a new, separate puppy website. Why? Because you can't just drop off live, vulnerable baby dogs on strangers' doorsteps! When she comes into the office with her newly revised plan (including a vetting process for new owners), you will have the next perfect response already prepared: "How can I help?"

3. The situation: You dial up a big, multinational hotel corporation to confirm the reservation for your stay at a French-Polynesian resort next week--your only vacation of the year. "Hello," says the customer-service agent. She does not sound French-Polynesian, by the way. She does not even sound 14.

The response:
"My name is Leigh Newman. What's yours?"

The idea here is that by exchanging names and civilities, you're establishing a human connection that may lead to a more positive interaction. But let's say--just because it so often happens--that the customer-service rep can't find your records. She puts you on hold for a few minutes, only to come back on the line and say, nicely, "Nope! There's no reservation!" But she is willing to give you a similar room for triple the price. At that point, asking for her name is moot. She is not a ding-dong. She is going to put you back on hold for a manager. Or give you a fake name. Or give you a name without a last name or an extension. Or say that company policy is not to give out names. At that moment, you realize if you'd gotten the name of the very kind, polite woman (Dee-Dee) who had made the reservation six month ago, you could bring it up now. Strike with good manners--and a fat dollop of hope--first.

4. The situation: You're at a restaurant. You get up to go to the bathroom and see the famous owner of a company you admire sitting at the bar (or the author of your favorite book or the star of your favorite TV show). She is sitting alone--as amazing, talented people often are because everyone is too afraid and shy to approach them. You don't want to run up to her and say, "Sheryl Sandberg!! I love your work! In fact, I love you!" because then there is nothing for the poor woman to do except say, "Thank you," feel embarrassed and fall silent. You also don't want to run up to her and say, "Are you Sheryl Sandberg, the famous COO of Facebook?" So instead you stand there by the bussing station...wishing you could say something. But what?

The response:
"My name is Leigh Newman. I'm so interested in social media. What advice would you give to a person looking to enter into your field?"--all of which is a slight adaptation of what young Henry Cavill (now star of Man of Steel) asked Russell Crowe, back when Cavill was an unknown 16-year-old. First, as with the customer-service agent, introducing yourself is just plain polite. It also reminds the actor/mogul/author that she has something in common with you: you're both humans; you both have names. You don't have to be afraid of her. (And if it turns out that she needs to be afraid of you, she has your name.)

Second, praising an area of her expertise, without fawning over her personally, makes anyone feel open to talking; you're focusing on her interest, not her performance, love life, childhood or hangnails. The best part? You may just learn something that applies to something much bigger. "If you want to go for it, then really go for it," Crowe told Cavill. "Commit."

5. The situation: Your friend is having a rough time. Her boyfriend of two years broke up with her three days before their annual cruise (sticking her with the bill) and her boss promoted three lesser-qualified men over her. So it's not surprising that at the cocktail party the two of you attend, she has that second (or third) glass of industrial-grade Chardonnay, joins the conversation you're having with a random, attractive male lawyer and ends up in a meandering rant about men: those selfish, inconsiderate, always-land-on-top jackasses!

The response: "Sarah. I so see where you are coming from. Let's go grab a bite at that new restaurant around the corner and talk about it."

Why? Standing there blushing is only going to allow your friend to humiliate herself further. You're her friend; your job is to protect her. It's time to leave. But whispering something to the lawyer like, "Sarah had a little too much to drink," or "Sarah had a bad breakup," will make you look rude for speaking about her in third person (as Russell Brand so famously noted). A direct "Let's go home" is also tricky. She won't want to go home; she's drunk; time has stopped. Your job is to acknowledge the difficult thing that inspired the misguided monologue ("I see where you're coming from") and to get her out of the room ("Let's go grab a bite"). If you want, tip the coat-check girl a few dollars to hand your card to the lawyer with the phrase, "Men aren't so bad" on it, all the better. He'll probably call. Everyone finds a person who can save everyone's self-esteem--without flattery or obvious falsehoods--attractive.


KEEP READING: 10 Social Skills Everyone Can Master

More from Oprah.com:

6 of Nate Berkus's Most Dazzling Home Makeovers
Quiz: What's Your Worry Set Point?
Pastor Rick Warren: 6 Ways to Make the Most of the Hand You're Dealt in Life
Some of the Best Quotes to Point Your Life Forward