1) Girl at coffee shop. Order my usual (I know the guys there, so I get a discount - small blessings), and spot a not-too-shabby-looking girl reading a book while waiting. Decided to take a seat next to her, and casually inquire as to what she's reading. She didn't respond at first, so I went quiet, then tried again, this time a bit louder. It was only then that I noticed that she actually had earphones on, but they were obscured by her hair. She tells me it's a book on lizards, and I ask her if she has any pet lizards. We exchange a maximum of ten, maybe twelve words, and then she plugs the earphones back in. Since her answers seemed kind of sharp and had an undertone of "not interested" (or maybe I misread her), I decided to leave her alone, especially since she wasn't (from a completely shallow perspective) the kind of knockout looker that warrants maybe a bit of extra effort to chat up.

Notes: I might be bad at reading people. Maybe she was interested but shy and socially awkward. Or maybe she just wasn't interested. Either way, I gave it a shot and got no bite. Maybe I could try pushing it further next time, I seem to give up too easily, IMO. Considering I had just spent the better part of the day being an errand boy, I was really too tired to give a damn. Granted, I did notice as she left that she had the book Felidae poking out of her bag. I found that kind of funny, as I have met very few people who have ever seen the animated movie, and even less who had read the book.

2) Girl at the supermarket. Make eye contact, give her a kind of smirk, but she turned away shyly. Pass by each other several times, I saw her look down and smile at least once when I looked at her as she was passing by while I was looking at toothpaste. Was behind her in line, was thinking I could chat her up when we both got to put our stuff in our cars outside, but the cashier took longer than expected, and she left.

Notes: Would a simple "hi", or an observational comment as you passed her by been too hard?

3) Girl at the park. Just doing my usual walk around routine, run across two girls, probably first-year university, walking with their dog. As I'm passing by, smile at the blonde one, who immediately smiled back, and asked her what the dog breed was. Exchange maybe a maximum of 6 words, and move on. Then I reach the statue, where I turn around and walk back to my car, and either I was walking really fast, or they were walking really slow, since I managed to catch up to them. Restart my conversation with the blonde, who seemed pretty enthusiastic and exchanged a few words back and forth. Managed to successfully guess that the other girl was her sister, but then conversation slowed, and I, for some reason, became nervous and shut up. Reached my car soon after, and as I'm driving away, I notice the blonde glance back. Kept driving anyway, mentally kicked myself all the way home.

Notes: Silence is not the enemy. It is your friend. Just because you run out of something to say, doesn't mean that you can't restart the conversation further on. You keep forgetting this.

4) Girl in the city. Notice her walking around, snapping photographs. Catch her gaze a couple of times, and exchange smiles. Eventually walk up to her and tell her she seems familiar to start up a conversation. She seems friendly, and seems to be a bright girl. Out of town, on holiday visiting her friend. Chat for a bit, fail to escalate, then she mentions that she's going to check out the theater a block down. Say goodbye, let her walk away.

Notes: Should have escalated, found out if she had spare time for a chat over drinks, or get her number otherwise. Instead I spent too long faffing about, and hell, she seemed to be expecting me to escalate now that I think about it.

5) Girl at the gym. Lifting weights, she walks in, so I just look at her out of habit, and smile when our eyes meet. She gives a warm smile back, says "Hi!" as she passes by and I respond the same. Make some occasional comments to her as she's passing by, during a pause in-between sets, I walk up to her and start talking to her, by first making an observational comment about the weights she's using. Ask if she's a newcomer, since I had never seen her at the gym before, she seems pretty friendly and enthusiastic, and she actually took charge of the conversation by introducing herself, asking my name, going for a handshake, etc. I figure, hey this girl seems into it, she seems nice and fun to get along with, chat a bit more, before it goes quiet and she moves onto the treadmill whilst I go to do some pull-ups. Exchange words several more times as we move around, and as she's leaving, initiates exchange of goodbyes. Should have noticed that there way another guy coming in with her, and leaving, guess when I saw him talking to her, I just figured he was another guy trying to chat her up. Eventually decide, eh, what the hell, run out to catch up with her and the guy to ask her out. Just to avoid awkwardness, ask the guy if he was her boyfriend, he confirms, ask her the same, she confirms. They seemed a bit taken aback at first that I ran out just to try and ask her out, but once that was done, said goodbye again and went back inside the gym to finish my workout.

Notes: Guess she was one of those girls that is just friendly to everyone. Kinda disappointing, and should have realized that the guy was her boyfriend, but ah well. Still feel proud of myself for actually chasing her up to ask her out, instead of just hanging around at the gym and nursing fantasies of that being "her good friend". Better just get it over with. But man, come on, every time I get a good, friendly interaction going with a girl and ask her out, she just has to have a boyfriend.

Yet another day closer to achieving intimacy with a lovely girl.