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Start a casual conversation before getting into anything romantic.
But most every other friend of mine has a story about seeing someone on the subway, or the bus, or the line at the drugstore, and wanting to talk to them but not knowing how - and letting the moment pass them by.
How do you strike up a conversation with someone you don't know without coming off as creepy, while still making it clear that you're interested?
The short answer: It's hard.
For the long answer, let's turn to Jordan Harbinger, host of "The Art of Charm" podcast, where he shares tips on networking and relationship building, romantic and otherwise. Harbinger recently appeared on another podcast - "The James Altucher Show" - and gave some pointers on the dilemma mentioned above.
Back when he was single, Harbinger said he spotted a woman on the train who was texting furiously.
"Are you gonna write the whole book on your phone?" he asked her.
It turned out the woman was really open to conversation, and told him how she wanted to text her friend, but there was no service underground, so she was preparing a message she could send as soon as they surfaced. She and Harbinger ended up getting into a discussion about how annoying it would be if there were cell service on the train, and how they appreciated the respite from technology.
The trick here is that Harbinger didn't open with a traditional pick-up line (Altucher suggested, "I didn't get your text. Can you resend it?") or anything that would directly signal his interest.
That's because he put himself in the woman's shoes and tried to figure out what she'd be thinking or worrying about if a random guy started talking to her - he assumed it was safety. So he tried to disarm her.
"That was a pretty nonthreatening general thing to say," he said of the opening line he ended up using. After they established some rapport, he could theoretically ask for her number. (Harbinger didn't reveal on the podcast whether he did that.)
Another trick he sometimes uses?
Instead of speaking directly to the person he's interested in, he'll talk to that person and someone else seated near him. "Now it's just a conversation and I happen to be leading it," he told Altucher.
Harbinger's advice jibes with research on flirting: A 1986 study found that women generally prefer "innocuous" opening lines to direct openers or pick-up lines. Think, "Which team are you rooting for?" or, "How do you like the band?" (Men, on the other hand, tend to prefer direct lines, like, "Can I buy you a drink?")
Keep in mind, though: Harbinger says not everyone will be open to conversation. This is just a way to boost your chances of getting the object of your affection to talk to you. He told Altucher that getting good at this kind of relationship building ultimately comes down to persistence and patience.
Citing the work of the psychologist Anders Ericsson, he said it's all about "deliberate practice," which involves having a goal and figuring out exactly what went wrong if you don't reach it. What can you say next time that won't put the person on their guard or turn them off?
The takeaway here seems to be that it helps to imagine how you would feel if you were that person and someone approached you while you were going about your business. If you'd feel even a little bit skeeved out by the line you're about to use, it's probably best to find another one.