CHOOSE THE RIGHT TIME
There’s really only one hard-and-fast rule about the right point in a relationship to get lingerie for a woman: You can only do it after you’ve slept with her. Do it any sooner and and the perv alert will instantly go off in her head. But that’s not the only thing that you have to keep in mind.
How long you should wait after you’ve had sex depends on the woman in question, according to Amanda Horan Kennedy, psychotherapist and CEO of the lingerie line Sassybax. “If you’ve noticed that she always wears matching bra and panties, she’ll probably appreciate the gift early in the relationship.”
If, however, she tends to wear whatever happens to be clean (if she doesn’t even worry about it being clean, you’re gonna have worse problems than figuring out how to buy her underwear), wait at least a month. That way she won’t think you’re being critical of her current underwear selection or trying to turn her into someone she’s not.
And whatever you do, avoid giving her underthings on her birthday. “For a birthday, she wants something she can show off to her friends,” Kennedy says. “Plus, lingerie is as much a gift to the giver as it is to the recipient, so don’t make her special day about you.” All other occasions— New Year’s Eve, Valentine’s Day, Secretary’s Day — are game on.