Dear Dr. Date,
During the past year-and-a-half I have had classes with a very attractive girl. We have developed a strong friendship, see each other often and spend lots of time together with a larger group of friends. Recently, my feelings for her have turned romantic. When we’re together she flirts with me, but no more than she does with other guys. Every day I sit next to her in calc class, and listen to her complain about how she thinks she’s “an undateable toad.”
Dr. Date, I know your advice is always to come out and ask her how she feels, but I really don’t want to jeopardize our friendship with each other or our circle of friends by doing this. How can I express my feelings for her without making our friendship awkward?

— Clueless in Calculus

Yes, my advice is to be open and honest about how you feel, but this is never as easy as it sounds. First off, you don’t just run up to her on the street and blurt out, ‘I want you to be my woman.’ At the same time, you need to let her know something about how you feel.
The problem (and solution) usually lies within the huge gap between what you are thinking in your head and what you’ve actually expressed to her. Most often, we mistakenly think a person knows how we feel, but they usually have little clue. Those innuendoes and glances that we think are so obvious often go unnoticed. You can have an all-consuming crush on a person and flirt with them constantly, but that person might only pick up on a few tiny messages and simply think you’re being nice.
With that in mind, I think you should be more playfully flirtatious and bold. You missed a big opportunity to do this when she was joking about being an undateable toad. This is where you, in your own witty style, let her know that you’d like to go out on a date with her. Make it fun and make it light. Nothing cramps a first date like the weight of the future.
You learn so much about a person after only one date. It’s usually clear that either some spark is there or it isn’t. I’d like to get all of you to the point where this first date isn’t so daunting. It’s really just an extension of your first meeting. At some point after several dates, a relationship begins. A first date is not a relationship. It’s just a chance for you to go out, have fun and learn more about an interesting person. Try to keep the simplicity of this in mind next time you talk to your friend.