Search Results: how long to wait before asking out

Long story short, I've known this girl for 5 years but never really talked to her until we started freshman year of college (this year). We live right next to each other. From August to early October we hung out 3-5 times a week and got to know eachother very well and grew pretty comfortable around each other. In fact I have even fell asleep in her room before. Even though I was falling for her in that time I did nothing. Eventually she got a boyfriend and we didn't hang out as much anymore. We just started 2nd semester and she sent me a text Monday night, leg day tomorrow? We are workout buddies again like 4 months ago, and I don't think she's with her boyfriend anymore, just dating other guys now. I really like her and I felt terrible when she got a boyfriend and I regret that I didn't tell her how I felt. Now might be my chance. We have a good friendship now but I feel like she was interested in me at one point, and I am now. Anyway here is my plan.

When we are eating dinner next time, I am going to bust out a notebook and pencil. I will be like "okay I need to show you something." I will draw a stick figure in a hole, and say "That's me, I'm stuck in a hole and can't get out on my own." Then I will draw a stick figure her outside the hole and say "you're standing right there (I draw a ladder next to her), and you have a ladder." Then say something like "If you throw that ladder down to help me I can put in a little effort and get out of the hole." Then I will pause for a couple seconds and be like, "oh wait I forgot something, this hole has a name." Then I will draw a sign next to the hole and label it FRIENDZONE. After that I just watch her and see what she says. Might be dumb idea, but it seems better than saying flat out "I really like you." It's casual and kind of funny. Of course if she doesn't get it or takes a long time to answer I will just say "basically what I am asking is will you go on a date with me?"

By the way I am 18 not 28!!!