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Looking for the Right Moment
Read her positive signals. The appropriate time to whisper in a girl's ear can vary, but at least make sure that she's enjoying your company, and hasn't been shying away from you. If she laughs at something you say, smiles frequently while you're talking, and consistently makes eye contact with you, the chances are good that she finds you likable. If you began speaking as part of a group, and she breaks off from that group to talk to you alone, this is also a likely signal that she's interested in getting to know you.
Consider testing the waters. A good way to get an idea about whether she'd be comfortable with close contact such as a whisper, is to touch her hand or arm lightly while making a joke or confiding something. If she seems okay with this, then she'd probably not have a problem with your whispering to her. But if she draws back from you, and the tone of the conversation deteriorates after that, it's best not to try making any further contact.
Offer to buy her something first. If you're at a bar or nightclub, a good way to begin working your way to earning her affection is to ask if you can buy her a drink. If she accepts, this is an indication that she'll at least give you a chance to show that you're worth her time. If she's with a group of friends, offer to buy them something as well. If you're up to something subtler, and there happens to be a jukebox onsite, offer to buy her a few songs. If you ask her for a drink, and she says no thanks, explaining that she doesn't drink, take her word for it. But don't consider it as a rejection, even if you offer her a non-alcoholic drink without success. She may really just not be thirsty. For the jukebox, you could try, “Did you notice the jukebox in the corner? How about I get some platters spinning—anything you'd like to hear?”
Suggest an alternative activity beforehand. A bold gesture such as whispering in her ear may come off more naturally if the two of you are already doing something fun together. If you're at a bar, getting her to play an arcade game, pool, or darts with you will allow you to shift the tone of your interaction from formal to informal. Once you've a had a laugh together, you'll both be more in the mood for flirting involving bodily contact. Some ways to suggest this would be, “How about getting away from the crowd for a bit and trying our hand at Space Invaders?” or “I'm sure you know a good trick shot or two at the pool table. I'd be thrilled if you could show me.”
Choose an appropriate phrase. Be sure you know just what you're going to say, and how to say it, before whispering. Pretend you're on stage, and need to deliver your lines convincingly. You can whisper sweet nothings, secrets, or whatever else you fancy, as long as it will fit with the tone of the conversation you've already been having. If you want to make her laugh, and the joke is slightly off-color, you can whisper the punch line in her ear. If you'd like to come off as seductive, be careful not to use descriptive language that might offend most people, especially if you've only recently met her. If you've only met that day, try something simple and attentive that is not likely to offend, such as, “Has anyone told you how pretty you look tonight?” If you're feeling confident, you could try a suggestive phrase such as, “Have you seen how beautiful the moon looks tonight?”
Making the Approach
Stand or sit to the side of her. This will make it easier to whisper in her ear, which would be awkward directly from the front—it could appear as if you're going in for a kiss. If you'd still like to add some element of surprise, wait until she turns her head away from you before approaching her ear. If you already know her fairly well, you could try to surprise her by whispering from behind her. But do this only if you know she's not easily frightened, since it could produce a big scare. If you especially want to avoid startling her, you can try placing one hand gently on her shoulder before approaching her ear.
Cup your hand around your mouth. If you're on her right side, use your right hand to cup your mouth. If you're on her left side, use your left hand to cup your mouth. This way your whispering will be shielded from the hearing of any others who might be in front of her or to her side. If her hair is covering her ear, avoid brushing it away if you've just met her that day. If you've been on at least a couple of dates, brushing her hair aside should be acceptable.
Approach her ear. If you've only just met the person, avoid making direct contact between your cupped hand and her ear. If she's your girlfriend or if you've been dating for some time, it should be okay to press your hand lightly against her ear while whispering.
Ensure that she can hear you. If you're in a noisy area such as a busy bar or at a party, you may have to speak above a whispering tone in order for her to hear you. Be careful not to yell, though. A tone slightly above a whisper should be audible, since your mouth will be close to her ear. But if there is little or no background noise in your area, speak slowly in a whisper.
Follow up according to her reaction. If she immediately moves away from you even before you get a chance to whisper, or after, you'll know to avoid trying to make physical contact with her for the moment. But if she responds with a smile, giggle, and sustained eye contact, you've done well. Yet be careful not to take a positive reaction as an invitation to move a step beyond by hugging her or holding her hand right away. Be content with having made her laugh and smile, and wait for a response from her, such as touching your hand or moving closer to you, that shows she's probably comfortable with more involved flirting.
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