Scary Dating Moments - Solved

by Kimberly Dawn Neumann
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Terrified to ask for someone’s phone number, go in for the first kiss, or (yikes) say those three little words? Never fear—help is here.

Sure, dating is filled with plenty of warm-and-fuzzy, feel-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, etc… and suddenly you forget every trick in your how-to-meet-someone arsenal. Quick, don’t just stand there paralyzed and let
f saying “I love you” leaves you tongue-tied, consider writing it instead.
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 the old standby ‘Hello, how are you?” encourages Neuharth.

Or, try a little dating humor. Dating guru David Wygant, founder of, 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 answer, “The part of walking over and breaking the ice.” Wygant says this works because it doesn’t come off as a line. “It’s one of my favorite approaches because it’s real and allows you to move easily into introductions or conversation without awkwardness since you’ve already poked fun at yourself and the process,” he says.

You can also give yourself approach-confidence by having a couple common questions and short, funny stories in your back pocket. Then if you freeze you can pull from your data base. “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. “’What brings you here?’ or if you’re at a party, ‘How do you know the host?’” Other good in-a-pinch questions include asking about siblings, vacation plans, hometowns and favorite sports teams. For stories, tie in current events or trivia.

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 hottie’s phone number into your cell. Fortunately, there are some simple ways to facilitate your digit-seeking efforts.

To begin with, always start your number 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?” says Laurie Puhn, J.D., communication expert and author of Instant Persuasion. 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 to, “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 persons pen to write your personal number or email on it in front of them. “If you’re already prepared, you can appear too indiscriminate, horny 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 surrendered yours.

Scary dating moment #3: Going in for the first kiss
It’s just a little lip-lock… 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 because you think you should,” says love coach Rinatta Paries. “Only kiss because you’re enjoying your time together and feel closeness 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 you
Most likely they’ll be impressed by your confidence and accept the kiss.
then spend the whole first date worrying about whether or not you’re going to have that kiss.” A better bet? Do it unexpectedly and well before 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 they’ll be impressed by your confidence and accept the kiss.”

You can also take the pressure off by keeping them 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,’” says Wygant. Then during the second date feel free to go in for the kiss at any time. “It’s fun and makes the other person anticipate it!”

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 consider asking for exclusivity. But how do you propose that he or she ditches all other prospects for you?

First consider if you’ve allowed the relationship appropriate time to develop. 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 dating only each other feel for you?” Also keep in mind that exclusivity can become an issue for some women when they’re contemplating entering a sexual relationship. If that’s your situation, Nancy Slotnick, founder of, suggests saying “I do want to sleep with you, but the reason that I’m not is that I only have sex in the context of an exclusive relationship, and it didn’t seem like we were there yet.” Then even if he proposes exclusivity, don’t sleep together that night because it could be an empty promise. “See what his actions look like in the few days after that: Does he pull back and wait longer to call or does he send you a dozen red roses saying you’re the only girl for him?” asks Slotnick. “If he does the latter, then you have a keeper.”

Scary dating moment #5: Saying “I love you”
Three little words. Amazing how uttering them 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. That said, most of our experts felt at least a few months of dating are necessary to know that you’ve moved beyond those first phases of infatuation, attraction, and excitement to know your feelings are for real. (And whatever you do, don’t say “I love you” for the first time when you’re having sex. Too many hormones are involved, and your date may not be able to take you seriously.)

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 you intended will react when you break out the big confession. If saying it gets you tongue-tied, consider writing it instead—in an email, birthday card, or other sweet note. And no matter what, you should steel yourself for the possibility that this person won’t necessarily say “I love you” back right then and there. “Every person takes a different amount of time to feel comfortable with the label ‘love,’ so be patient,” says Puhn. The bottom line is, no matter what happens, you should congratulate yourself for having the guts to get it out there.

Kimberly Dawn Neumann is a New York City-based freelance writer whose work has appeared in such publications as Cosmopolitan, Marie Claire, Fitness, and frequently for Happen. She thinks dating can be terrifying, but that doesn’t stop her from trying.
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