Assume attraction. You know that you are sexy, and no matter if she’s “taken”, lesbian, a happy single, she likes to feel desirable. You’re in a position to give her that feeling. You can open up the interaction with a line as simple as this: “Hi. What’s your name?” You can also establish a mystery: “You’re drinking green tea, right? That tells me a lot about your personality.” Then don’t tell her what it is. Right before approaching, you can start humming or softly singing to yourself, it bridges the gap between not speaking and speaking – you’re already in “talk mode” when you say your first words to her.
Tease Her (But Don’t “Neg”)
Playful teasing is a great way to break the ice and get her smiling and laughing. If she says something like “My friends sent me to the bar to get their drinks,” you can respond with “Jeez, sounds like they needed a break from you!”
Alternatively, you can make it even lighter hearted and play it safe by accusing her of staring at your butt while you were making a point.
Make sure not to overdo the teasing, though; you’re trying to flirt with her, not roast her at the Friar’s Club. Speaking of which, you iliar with the term “negging.” If not, here’s how Wikipedia describes it: [R]
“Negging is a rhetorical strategy whereby a person makes a deliberate backhanded compliment or otherwise insulting remark to another person in order to undermine their confidence in a way that gains approval.”
Why anyone would think the key to winning a woman’s affections is to make her feel like crap is beyond me, but for some reason, some people put a lot of stock in this idea. Don’t be one of those people – negging is a gross and demeaning practice, and more importantly, it doesn’t work. [R]
The case study demonstrates that “sensitivity” is the second most desired characteristic in married women, with “honesty & trustworthiness” in first place… polar opposite characteristics to negging.
Playful Opportunities With Double-entendres
She’s talking about her travels: “I spent a lot of time down south.” Say: “Down south?! You dirty girl!” Look for opportunities to introduce playful sexual innuendo into a conversation – if you set your mind to it, you’ll be amazed at how many things you can “accidentally misinterpret” as sexual hints. At some point, tell her: “Look, I realize I’m hot, but please stop your constant innuendos. I’m not that easy.”
Don’t Compliment Her (At First)
A lot of guys think they have to compliment a woman to make it extra-clear that yes, they do find her sexually attractive. While your honesty is certainly appreciated, it’s also overkill; she already knows that based solely on the fact that you’re approaching her.
Part of the fun of flirting is the implicit admission that each person finds the other attractive. Explicitly stating it is like handing someone a birthday present and announcing “It’s a book” before they can open it – it takes all the mystery out of the encounter.
A Note About Confidence
Many people struggle with flirting because they think they lack the self-assuredness to effectively pull it off. It’s true that these tips really only work if you present yourself as confident; otherwise, the results will be less than stellar. (Probably somewhere between “awkward” and “nightmarish,” if I had to ballpark it.)
Now, this would ordinarily be where I’d divulge some extremely simple method that would magically instill you with boundless confidence. Unfortunately, that’s not how confidence works; it’s just one of those things that comes with time and, yes, practice. If you’re lacking in confidence, all you can do is fake it ‘til you make it.