Handling scary dating moments

Sure, dating is filled with plenty of warm-and-fuzzy feelings and good times. But, in honor of Halloween, let’s look at the scary stuff. As anyone who’s ever asked for someone’s phone number or gone in for a first kiss can tell you, certain moments in the courting process can be, well, downright terrifying. But fret not: With a little expert guidance, you can fly through these date-night frights with nary a shudder. Try our advice for some typically panic-provoking moments below, and pretty soon you’ll be saying, “That wasn’t so scary, was it?”

Scary Dating Moment #1: Breaking the ice

Some enchanted evening, you may find your true love across a crowded room or in the bookstore, on the subway, at the coffee shop, or somewhere else... and suddenly, you forget every trick in your how-to-meet-someone history. Don’t just stand there frozen, or you could let someone special slip away! “Say whatever pops into your head — and say it within two seconds of thinking it,” says Dan Neuharth, Ph.D., a therapist and author of Secrets You Keep From Yourself. “The longer you wait, the harder it gets, and spontaneity usually scores points with potential dates.” Afraid your clever quotient has been stunned along with the rest of you? No worries! “There’s nothing wrong with an old standby: say, ‘Hello, how are you?” encourages Neuharth.

Or, you could try a little dating humor. Dating coach David Wygant suggests walking over to your prospect with a smile and saying, “I really hate this part.” Most likely the response will be, “What part?” to which you reply, “The part where I walk over and break the ice.” Wygant says this works because it doesn’t come off as a pick-up line. “It’s one of my favorite approaches because it’s real and allows you to move easily into introductions or conversation without any awkwardness, especially since you’ve already poked fun at yourself and the process,” he says.

You can also boost your confidence about approaching someone by having a couple of common questions and short, funny stories in your back pocket for breaking the ice. Then if you freeze up, you can pull something from your introduction arsenal. “The easiest opening line I know is a question about the event or place itself,” says JoAnn Magdoff, Ph.D., a New York City-based psychotherapist. “Ask, ‘What brings you here?’ or, if you’re at a party, ‘How do you know the host?’” Other good questions to use in a pinch include asking about siblings, vacation plans, home towns and/or favorite sports teams. For stories, tie in some current events or trivia facts.

And finally, remember that you’re trying to make an impression. “Think about what you’d like your date to know about you and lead the conversation in that direction, but keep it brief,” says Dr. Magdoff. In other words, don’t talk incessantly about yourself. Give the person a taste and leave him or her wanting to know more.

Scary Dating Moment #2: Asking for a phone number

You’ve managed to get things rolling, but now, all you can think about is how to shift from pleasant chit-chat to programming this person’s phone number into your cell. Fortunately, there are some simple ways to facilitate your digit-seeking efforts.

To begin with, always start your quest with a little flattery. Yes, it will get you everywhere (or at least up your chances of success). “Try saying, ‘I like chatting with you. I wish we had more time, would you mind if I gave you a call?’” suggests Laurie Puhn, J.D., communication expert and author of Instant Persuasion: How to Change Your Words to Change Your Life. The same rules apply online. Puhn suggests emailing something like, “You seem very interesting, I’d enjoy getting to know more about you” before moving on and asking, “Can we speak on the phone?”

Another good tactic? Give out your number first. Dr. Magdoff recommends handing over a business card but borrowing the other person’s pen to write your personal number or email on the back. “If you’re already prepared you can appear too indiscriminate or calculating rather than spontaneously interested,” says Dr. Magdoff. And if you really don’t want to take any chances, ask for his or her number after you’ve already given yours.

Scary Dating Moment #3: Going in for a first kiss

It’s just a little smooch… so why is it so nerve-wracking? Kisses are wonderful expressions of affection, so stop second-guessing yourself and just do it — but only when you’re ready. “Never kiss someone because you think you should,” says love coach Rinatta Paries. “Only kiss someone because you’re enjoying your time together and feel a bond forming.”

Once you’re primed, however, there is definitely a preferred pecking order. “The first kiss should not be at the end of the date,” says Wygant. “It’s way too planned, and then you spend the whole first date worrying about whether or not you’re going to have that kiss.” A better bet? Do it unexpectedly and long before you two are saying farewell. “If you’re walking the person home or on your way to a movie after dinner, these are good times,” says Puhn. “Then just get close, smile and lean in… most likely your date will be impressed by your confidence and accept the kiss.”

You can also take the pressure off by keeping your date guessing. “At the end of the date, say, ‘I bet you think this is the moment that I’m going to kiss you, but I had such a great time I want to save it for the next date,’” suggests Wygant. During the second date, feel free to go in for the kiss at any time. As Wygant notes, “It’s fun, and waiting makes the other person anticipate it more!”

Scary Dating Moment #4: Asking for exclusivity

Does the very thought of anyone else touching your date infuriate you? Then it might be time to talk about dating each other exclusively. But how do you propose that someone ditch all other dating prospects for you?

First, consider whether you’ve allowed the relationship enough time to develop properly. If you’re seeing each other regularly — about twice a week for a month, at minimum — then it’s absolutely appropriate to say, “I like spending time with you and I want to see where this will go. What do you think about being exclusive?” or “It feels pretty natural to keep time open for each other at this point — how would you feel about dating each other exclusively?” Also keep in mind that for some people, exclusivity is an issue when they’re contemplating introducing a date to friends and family. If that’s your situation, say so before agreeing to see each other again. “See what your date’s actions look like in the few days after that. Does this person pull back and wait longer to call, or enthusiastically agree?” asks Nancy Slotnick, founder of and author of Turn Your Cablight On: Get Your Dream Man in 6 Months or Less. “If he or she does the latter, then you have a keeper.”

Scary Dating Moment #5: Saying “I love you”

It’s amazing how uttering those three little words to someone for the first time can be the scariest dating moment of all. Why? Probably because your heart is on the line. This is why the decision on timing is yours alone to make. That said, most of our experts feel that at least a few months of dating are necessary to know that you’ve moved beyond those early stages of infatuation, attraction and excitement to be sure that your feelings are genuine.

From there, try easing into it with a “I think I’m falling for you” or “I could totally see myself falling in love with you.” That way, you can gauge how your intended will react when you break out the big confession. If saying it gets you tongue-tied, consider writing it down instead — in an email, birthday card, or other sweet note. And no matter what, you should steel yourself for the possibility that you won’t necessarily hear “I love you, too” right then and there. “Every person takes a different amount of time to feel comfortable with the label ‘love,’ so be patient,” advises Puhn. The bottom line: No matter what happens, you should congratulate yourself for having the courage to put your true feelings out there.

Kimberly Dawn Neumann ( is a popular New York City-based freelance writer whose work has appeared in such publications as Cosmopolitan, Marie Claire, Redbook, Maxim and frequently online. A certified dating/relationship coach, she’s published two books: The Real Reasons Men Commit and Sex Comes First and is the founder of

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