I've finally found the courage to give myself an ultimatum, I will ask a colleague out tomorrow;

I work retail from on an early morning shift for the summer, and I have had an interest for a girl working in another part of the store.

I have low self confidence and self-esteem, but I have a feeling she was interested as well, unfortunately because of my aforementioned defaults, I couldn't try to seriously initiate something.

After a couple weeks working I noticed her and thought that if I was to try something it would be with her, she works in another part of the store, and we sometime meet at the cardboard recycling dump, or in the elevator to our stock. (I'm on the 3rd and she's on the 2nd floor).

I gained confidence when a couple times she would come get me at the the third floor from the second before going down the the first (we have see-through floors). meaning she intentionally went out of her way to have a chat, or so I hope. (nobody ever does this 'elevator pick-up ride' at the store). She would also joke when we rolled nearby in the store.

My first steps toward my goal was to try to get as many elevator ride together as possible, so that we could chat a bit (barely 20-30 sec). So when I knew she was below on the 2nd floor, I would take longer or less time than usual to load up my transpal than usual so that when I saw/heard her rolling toward the elevator, I would go there first and pick her up on my way down. It worked quite well and after 7-8 rides it's not an awkward "hi" or anything, we're talking and joking about stuff etc.

I also lost confidence a few times since she does chat and casually laugh with a lot of other employees, and one in particular has his break at the same time with her and sometimes climbs up the the 2nd floor and have a chat with her there jut before the end of shift. To me it seems like he's trying hard but she not interested (or so I hope). But it goes to show that she might just be talking to everyone, and/or that she's not interested in more than chatting. I also think that the longer I take to make a move, the more she will find the situation boring and lose interest (again, if she ever has some).

I said to myself many times to ask her what she was doing on [enter day here] and/or if she would like to go grab coffee in town, but each time I would not get as many elevator rides as I wanted to (we kinda need to be alone in the stock for this as I don't want people to hear, and also to have at least met once or two before as asking her out at 5:30am in a dark industrial elevator would be weird)

But yeah, tomorrow I've decided that I would ask her out at any occasion, because it's been 2 and a half week of half-assed efforts and a mini roller coaster of emotions. Time to find out what's going to happen.

Please give me thoughts on this!