To know how flirt with a friend successfully, one has to use charm, tact and care in not going too far. Flirting with a friend can be very enjoyable, since you know the person so well already, but it could lead to something more if you’re not careful.
- Know the boundaries. If you flirt with a friend too aggressively, it’s going to put her on the defensive and wonder what’s going on. Playful touches and slight innuendo are all fine, but handfuls of ass and crude jokes about what you want to do to her in bed are going to send your friend backpedaling.
- Ease into it. If you have not flirted much with this friend before, you have to start off slowly, with very non-threatening flirtations. Ramping it up too fast is going to raise alarm bells in your friend and perhaps scare her away. To flirt with a friend, start with little, non-offensive things and then move on from there.
- Wait until she’s in a relationship. That’s right. Don’t flirt with your friend when she’s single, but when she’s dating someone. When your friend is single, your flirtations might come across as overtures that you want to date. If she’s not ready for that it’s going to push her away, potentially. To flirt with a friend, wait until she’s in the security of a relationship. Your flirtations will remind her that she’s still deemed attractive by other men, but without the concerns that you might be seriously coming on.
- Use your knowledge. You probably know a fair amount about this friend, including dating history, her friends and her background. Use this information to your advantage to flirt in ways that you know she likes and say things that will get her to flirt in response. If you want to flirt with a friend, use the intimacy that’s already built up between you.
- Pick your spots. Since this is your friend, you know you’re going to be able to spend a lot of time with her, be it over dinner, late-night drinks, brunch or at a museum or amusement park. So, don’t get impatient about flirting. Don’t do it when she’s in a bad mood, when she’s tired or other bad times. You can pick your spots. To flirt with a friend, wait until she’s most receptive, and you’ll get some flirtation in return.
Rabin, Susan. How to Attract Anyone, Anytime, Anyplace: The Smart Guide to Flirting. Plume, 1993.