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Super-Simple Pick-Up Strategies


If you’ve been away from the dating scene for a while and your flirting skills are a bit rusty, try these easy icebreakers from a professional matchmaker.

By Rachel Greenwald

f you’ve been out of the dating scene for awhile, you’re probably not used to approaching attractive strangers. Yet you see them everywhere: that cute man in the produce section at the grocery store, the intriguing woman across the field at your son’s soccer game. But how can you make contact without resorting to cheesy lines like “So, do you come here often?” Next time you see someone appealing, try turning a chance encounter into a potential date with the strategies below.

Act quickly. When someone catches your eye, don’t hesitate. Often there is only a small window of opportunity before the
Ask a question that requires more than a “yes” or “no” answer.
moment passes and the stranger is gone. If you believe in fate, think of it this way: That interesting person standing in line next to you at the post office may have been put there just for you.

Keep it simple. In that brief window of opportunity, what can you say? Try “Hello.” No, it’s not clever, sassy, or scintillating, but it’s a time-tested classic and it works. (Don’t forget a friendly smile!) It’s also a good gauge for whether someone wants to interact with you; not everyone is in a good mood, has time to chat, or is single—even if you don’t see a wedding band. If you receive a smile and a “hello” back, the natural response is to make a comment about your surroundings. Perhaps “Why do you think the line is so long here today?” or “How do you know our hostess?” This is a casual and non-threatening way to open the door for dialogue. The key is to ask a question that requires more than a “yes” or “no” answer. You want to create a bridge to further discussion, rather than start a dead-end exchange such as “Isn’t it beautiful out today?” which may only get you, “Yes” in response.

Stay current. Before you leave your house each day, be sure to read the newspaper or watch the news on TV. Staying abreast of current events (including sports events) allows you to comment quickly on something interesting or quirky—after all, you never know who you’ll bump into throughout the day. Think of one question each morning about a current event and commit it to memory. Something humorous is nice, but even a straightforward “Did you see the news this morning about (fill in the blank)?” can be a great icebreaker.

Consider a conversation prop. If you’re ultra-shy or ultra-rusty, wouldn’t it be great if someone else approached you first? You can put yourself in that position by carrying a “conversation prop” if possible. Sample props might include: a travel book, sport equipment, or even an item of clothing with a foreign slogan, sports team, or university logo on it. Choose something that relates to your interests or reveals something intriguing about you. A single man or woman who
Act fast before the moment passes and the interesting stranger is gone.
would like to meet you might see your prop, make a comment about it, and start a dialogue. You’re making it easy for someone to approach you. While this method is a “passive” one, it’s nice sometimes to let the initial responsibility fall to the other person.

Close the deal. Once you have made contact and exchanged some initial banter, you’ll want to make sure you will see this person again. You should always have cards with your contact info with you (business cards are preferable, but if you don’t have any, make your own cards at Kinko’s and include your name, phone number, and email address). If it feels right, you can say directly, “I’d love to chat with you again; here’s my card.” Or, you can hand someone your card without being too forward by referring to something you’ve just talked about. For example, “If you remember the name of that book you loved, let me know. I’d love to read it! Here’s my card.” If you’d rather make the first follow-up move, ask for her (or his) card. Make sure you’re carrying a pen in case he or she doesn’t have a card. If all else fails or you’re at the gym without a pocket, commit the person’s last name and company name to memory so you can follow up. Sometimes that extra effort can pay off with a wonderful romance.


Rachel Greenwald is the author of the New York Times best-selling book Find a Husband After 35 Using What I Learned at Harvard Business School. She is also a dating coach and matchmaker. She is a frequent guest on The Today Show and has been featured in dozens of magazines from Oprah to People.
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