If I hadn’t seen it for myself, I may not have believed it. But with my own two eyes, I watched a man look at a woman and say, “Miss, I think you just dropped something.” When she stopped to look around, he paused for dramatic effect and added: “my heart.” I wondered: What would she do? Would her eyes roll down the street as she ignored him? Would she respond negatively with a look and/or snarky comment? I was rapt, awaiting her reaction. The funny thing is… she did neither of those things. Instead, she laughed, then he laughed — and suddenly, they were having a real conversation.

I’ve often wondered: Why did that particular line work? I have a few theories. First, it occurred at a down-to-earth party in the countryside and not at some black-tie event or random happy hour. The relaxed setting definitely had something to do with this pick-up line’s success. Second, it exuded an air of someone familiar with Jane Austen’s writing, which suited both the setting and the woman he tried it on (and who clearly enjoyed his playful, yet formal tone). Third, it occurred in private. It was spoken rather quietly and projected just between the two of them, so he didn’t have to worry about her friends judging his approach.

Related: The cheesiest pick-up lines of all time
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Of course, each line is specific to every person and setting to which it’s applied, and this disclaimer seems especially pertinent for men. “Most women hate — I repeat, hate — pick-up lines,” asserts Dr. Ish Major, dating expert and author of Little White Whys: A Woman’s Guide Through the Lies Men Tell and Why. “Or at least, they hate to believe that a man thought a pick-up line would actually work on them. That said, the key to a really good pick-up line is to make it not seem like one at all.” Fair enough! Nobody wants to sound stupid or inauthentic, but someone has to say something to break the ice, right? With that in mind, check out these six lines that have worked for others — including suggestions on how to make them work for you, too.

Effective pick-up line #1: [Dater extends hand and says] “Would you hold this while I go for a walk?”
“Unless the object of your affection is really hard-hearted or just completely not into you, this line makes people smile,” says Kimberly Dawn Neumann, dating/relationship coach and author of The Real Reasons Men Commit. “It’s sweet. It’s clever. It takes a minute to register and then when it does, the door is open for conversation. You can literally ‘walk away’ with the person of your dreams if he or she takes the bait. And if not, you can always say, ‘Well, that’s too bad! You know what they say: warm hands, warm heart’ (or something like that) and then gracefully make an exit.”

Related: 4 pick-up places men should avoid

Effective pick-up line #2: “Hey, I’m (introduce yourself). Can I take you out some time?”
Daters “miss initiative,” says Andrea Syrtash, relationship expert and author of It’s Okay to Sleep with Him on the First Date: And Every Other Rule of Dating, Debunked. “This pick-up line works wonders.” It’s bold, since it surpasses small talk and (hopefully) drops you directly into the first date-planning stage. It’s perfect for situations where you don’t have a lot of time (i.e., one or both of you are leaving an event and haven’t had a chance to really break the ice and converse yet) or social opportunities (as in, you’re at a business conference killing time between sessions and you meet on a five-minute coffee break before heading back).

Effective pick-up line #3: “I really like your [comment on anything interesting the person you wish to meet is holding, wearing, reading, etc.].”
“People respond well to compliments,” says Neumann. “The reason this line works is because it doesn’t come across as a line at all. You utter it to make another person feel good, but the likely result will be that you both engage in conversation… and besides, you can always follow up with further questions about said complimented item (which will allow you to keep the conversation going a bit longer),” explains Neumann. “On the flip side, if you’re looking to meet people, this is a great tactic. Consider carrying an interesting book or toting around a really bright umbrella or purse or similarly remarkable object. You are giving people an automatic opener if you ‘prop’ yourself with something that’s worth commenting on.”

Related: 5 ways to get his attention in 72 seconds

Effective pick-up line #4: “This party really surprised me with the (food, wine, view, entertainment…pick something).”
“Simply make an interesting or amusing comment about your surroundings,” suggests Dr. Major. “Just make an opening statement. When you speak in statements, it implies an openness and confidence. It’s the way old friends speak to each other…and since you’re trying to make a new friend, an opening statement is perfect! And this works great for men and women! The key is not to overthink it” — but do definitely try to keep it positive.

Effective pick-up line #5: “You look like trouble!”
This is one of my favorites, but it works only if you’re in a fun, relaxed setting (like a crowded party or bar) and only if it’s said in an easygoing manner and delivered with a genuine smile. A little teasing can go a long way, and nothing gets the flirtatious juices flowing faster than a little challenge… just be sure to err on the side of sounding playful and not mean-spirited, regardless of you or your potential love interest’s gender.

Effective pick-up line #6: “Hi (followed by a friendly smile)!”
I saved the most obvious icebreaker for last. “This is the absolute best pick-up line ever invented,” says Dr. Major. “It’s quick, clean, neat, unassuming, non-intrusive, friendly and pleasant.” It gets the other person to notice you and signals your interest at the same time. Here’s the thing: It’s likely that your flirting target has already noticed you, too, and has been waiting to see:

A: If you would approach, and
B: How you would approach.

Your only job in that situation is to have the courage to say something — i.e., break the ice. If someone likes you, he or she will pick up the conversation and run with it from there. If not, no harm, no foul. “Nothing ventured, nothing gained,” says Major. “At the very least, you can walk away knowing you were up to the task!”

Related: Seduction moves for shy daters

When it comes to choosing a pick-up line, follow these solid rules from the business world:

1. Know your person. When applied to dating, the rough translation is that before you speak, first try to get a sense of whether your opener to this potential Mr. or Ms. Right stands a chance of working at all. Does the person seem easygoing or uptight? Choose the line that you think will work best on your potential love interest.

2. Know your setting. Are you in the kind of place — a hayride, for example — where the homespun goodness of a sweet, yet slightly corny line could plant a big smile onto the face of your intended? Or are you at a sophisticated, pricey black-tie event where you’re more likely to come off like a fool fulfilling the terms of a lost bet? When it comes to lines — whether they’re good, bad or corny — context definitely matters. In the case of my first example (“my heart”), a gallant delivery wouldn’t hurt, either. If you’re going to make a grand gesture, commit 100% to it… don’t do it halfway!

Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Visit his website, follow him on Twitter, or email him.



Article courtesy of Match.com.