Should You Flirt with a Friend?

Whether or not you should flirt with a friend depends on several factors.  The results can either be delightful or devastating, so it’s important that you think about them before you begin flirting with her.  The first question to ask yourself is: “Why do I want to flirt with my friend?”  Is it because you’re naturally flirty and it just seems fun?  (This is likely the case if your friend is of your non-preferred gender.)  Or is it because you are actually interested in your friend?

If it’s the first, there are fewer risks to take into consideration.  Flirting often takes the form of joking and teasing that strengthens the bond between friends.  If he’s been your friend for a long time, you should be able to gauge how he’s react to your “advances”.  You may already flirt with one another to some degree.  Do you make eye contact frequently, smile at each other, and make casual physical contact (picking lint off each other, punching each other playfully, etc.), so ramping up your game shouldn’t be too difficult.  You can try using ridiculous pick up lines on him or joke the inevitability of your marriage.

There are some things to be aware of, however, even when you’re just flirting for fun.  No matter what your sexual orientation, she may become concerned or angry if you hit on her.  Men in particular fear being seen as “less of a man”, and may feel like others are judging him if another man flirts with him (perhaps especially if he’s into men but not yet out of the closet).  Some people will not be comfortable with same-sex flirting, even if you think it’s clear that it’s all in fun.  Oddly enough, there are people who would be okay with same-sex flirting that would be uncomfortable with cross-gender flirting.  While flirting with someone who may or may not or may not be attracted to the same sex is seen as “safe”, since it’s clear that because at least one of you is straight that nothing will come of it, whereas with opposite-sex flirtation, there is the possibility of confusion.  Finally, your friend might actually harbour feelings for you and flirt back, only to be hurt when it becomes clear that you were only joking.

Certain things are different when you actually are interested in your friend.  First of all, flirting is a great way to discover whether or not she might be receptive to your attention without being explicit and risking damaging your friendship.  After all, flirting is the art of expressing your interest without saying or doing anything to clearly indicate it.  In return, the object of your attention can tell you how she feels by using non-explicit words and body language.  If she even notices you’re flirting with her, that is.  Neither of you is exposed to ridicule and you may just find out if you should take that next step. 

In addition to the concerns for friendly flirtation, serious flirtation runs the risk of upsetting your friend or making him feel like remaining your friend or spending as much time with you is leading you on or just more trouble than it’s worth.  It’s up to you to decide whether finding out how your friend really feels about you is worth the risk of losing him altogether.  But look on the bright side: it seems more friends flirt happily than “break up”.