Terra's Past Letters

JJ

Dear JJ,

It's always a risk that you might "ruin" a friendship when you cross over into the boyfriend/girlfriend zone. You never know how she's going to react. But here's something to think about, the two of you have a solid basis for a friendship. (I'm assuming that since you've known each other for so long, you actually enjoy each other's company, as friends, and are comfortable enough with each other to talk honestly.) Here's what I suggest, instead of just blurting out "Want to go out with me?" how about if you ease into the conversation with an open-ended question like "Do you think it's possible for two people who have always been friends to become more than friends?" See what she has to say in response to that.

The idea here is to get the conversation moving in the direction of friends and romantic feelings. You might find out from her that she thinks it's a good idea for friends to date and that she has had those kind of feelings about you, in which case, it would be a "green light" signal to go ahead and ask her out. Or... you might discover, talking to her, that she thinks it's a really bad idea for friends to go out because of the risk to the friendship, in which case, you might decide that it's not such a good idea to ask her out at this time.

So, have a talk with her and see what you can find out about how she feels.... then write back and let me know what happens.

I hope this helps.